Safehold Inc. 10-K

Item 8. Financial Statements and Supplementary Data Index to Financial Statements ​ ​ ​ Page Reports of Independent Registered Public Accounting Firm (PCAOB ID No. 34 ) 39 ​ ​ Financial Statements: ​ Consolidated Balance Sheets as of December 31, 2022 and 2021 42 Consolidated Statements of Operations for the years ended December 31, 2022, 2021 and 2020 43 Consolidated Statements of Comprehensive Income (Loss) for the years ended December 31, 2022, 2021 and 2020 44 Consolidated Statements of Changes in Equity for the years ended December 31, 2022, 2021 and 2020 45 Consolidated Statements of Cash Flows for the years ended December 31, 2022, 2021 and 2020 46 Notes to Consolidated Financial Statements 48 Financial Statement Schedules: ​ Schedule II—Valuation and Qualifying Accounts and Reserves as of December 31, 2022 with reconciliations for the years ended December 31, 2022, 2021 and 2020 96 Schedule III—Real Estate and Accumulated Depreciation as of December 31, 2022 with reconciliations for the years ended December 31, 2022, 2021 and 2020 99 Schedule IV—Mortgage Loans on Real Estate as of December 31, 2022 with reconciliations for the years ended December 31, 2022, 2021 and 2020 100 ​ All other schedules are omitted because they are not applicable or the required information is shown in the financial statements or notes thereto. ​ 38 Table of Contents REPORT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM To the shareholders and the Board of Directors of iStar Inc. Opinion on the Financial Statements We have audited the accompanying consolidated balance sheets of iStar Inc. and subsidiaries (the "Company") as of December 31, 2022 and 2021, the related consolidated statements of operations, comprehensive income (loss), changes in equity, and cash flows, for each of the three years in the period ended December 31, 2022, and the related notes and the schedules listed in the Index at Item 15 (collectively referred to as the "financial statements"). In our opinion, the financial statements present fairly, in all material respects, the financial position of the Company as of December 31, 2022 and 2021, and the results of its operations and its cash flows for each of the three years in the period ended December 31, 2022, in conformity with accounting principles generally accepted in the United States of America. We have also audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (PCAOB), the Company's internal control over financial reporting as of December 31, 2022, based on criteria established in Internal Control — Integrated Framework (2013) issued by the Committee of Sponsoring Organizations of the Treadway Commission and our report dated February 21, 2023, expressed an unqualified opinion on the Company's internal control over financial reporting. Basis for Opinion These financial statements are the responsibility of the Company's management. Our responsibility is to express an opinion on the Company's financial statements based on our audits. We are a public accounting firm registered with the PCAOB and are required to be independent with respect to the Company in accordance with the U.S. federal securities laws and the applicable rules and regulations of the Securities and Exchange Commission and the PCAOB. We conducted our audits in accordance with the standards of the PCAOB. Those standards require that we plan and perform the audit to obtain reasonable assurance about whether the financial statements are free of material misstatement, whether due to error or fraud. Our audits included performing procedures to assess the risks of material misstatement of the financial statements, whether due to error or fraud, and performing procedures that respond to those risks. Such procedures included examining, on a test basis, evidence regarding the amounts and disclosures in the financial statements. Our audits also included evaluating the accounting principles used and significant estimates made by management, as well as evaluating the overall presentation of the financial statements. We believe that our audits provide a reasonable basis for our opinion. ​ Critical Audit Matter The critical audit matter communicated below is a matter arising from the current-period audit of the financial statements that was communicated or required to be communicated to the audit committee and that (1) relates to accounts or disclosures that are material to the financial statements and (2) involved our especially challenging, subjective, or complex judgments. The communication of critical audit matters does not alter in any way our opinion on the financial statements, taken as a whole, and we are not, by communicating the critical audit matter below, providing a separate opinion on the critical audit matter or on the accounts or disclosures to which it relates. Current Expected Credit Loss (“Expected Loss”) – Estimation of Fair Value of Underlying Collateral of Loans Exhibiting Signs of Financial Difficulty - Refer to Note 3 and Note 7 to the financial statements Critical Audit Matter Description The Company estimates its Expected Loss on its collateral-dependent non-performing loans where the borrower is experiencing financial difficulty using the estimated fair value of the collateral. The estimate of the Company's Expected Loss on such loans required judgment when determining the fair value of the collateral securing the loans. The Company records a specific allowance using a practical expedient in accordance with the CECL standard if the Company determines that the collateral fair value is less than the carrying value of the loan. The Company generally uses the income approach through internally developed valuation models to estimate the fair value of the collateral for such loans. In some cases, the Company obtains external "as is" appraisals for loan collateral. Significant judgments are required in determining the specific allowance, including estimates and assumptions regarding the fair value of the 39 Table of Contents collateral and other estimates. The determination of the Company’s specific allowance for these loans represents a critical audit matter given the level of subjectivity and judgement involved. Performing audit procedures to evaluate the specific allowance for non-performing loans required a high degree of auditor judgment, and an increased extent of effort to evaluate whether management reasonably and appropriately quantified the fair value of the collateral. How the Critical Audit Matter Was Addressed in the Audit Our audit procedures related to the determination of the fair value for those assets in which the borrower exhibits signs of financial difficulty as part of estimation of the Expected Loss included the following, among others: – We tested the design and effectiveness of controls implemented by the Company in relation to the calculation of the specific allowance, including management’s review of the fair value analysis performed in relation to collateral including related assumptions and inputs used within the fair value analysis. – We evaluated the Company’s determination of fair value of the collateral with the assistance of fair value specialists, by evaluating the reasonableness of the (1) valuation methodology; (2) significant assumptions made, including whether the significant inputs used in the model were appropriate and consistent with what market participants would use to value the collateral; and (3) mathematical accuracy of the overall valuation model. – We tested the underlying data used to develop the fair value to determine that the information used in the analysis was accurate and complete. – We considered whether events or transactions that occurred after the balance sheet date but before the completion of the audit affect the conclusions reached on the fair value measures and disclosures. ​ We tested the accuracy and completeness of quantitative data used by management to estimate the current and future economic conditions. ​ ​ /s/ DELOITTE & TOUCHE LLP ​ ​ ​ New York, New York ​ February 21, 2023 ​ ​ ​ We have served as the Company’s auditor since 2018. ​ ​ 40 Table of Contents REPORT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM To the shareholders and the Board of Directors of iStar, Inc. Opinion on Internal Control over Financial Reporting ​ We have audited the internal control over financial reporting of iStar Inc. and subsidiaries (the “Company”) as of December 31, 2022, based on criteria established in Internal Control — Integrated Framework (2013) issued by the Committee of Sponsoring Organizations of the Treadway Commission (COSO). In our opinion, the Company maintained, in all material respects, effective internal control over financial reporting as of December 31, 2022, based on criteria established in Internal Control — Integrated Framework (2013) issued by COSO. We have also audited, in accordance with the standards of the Public Company Accounting Oversight Board (United States) (PCAOB), the consolidated financial statements as of and for the year ended December 31, 2022, of the Company and our report dated February 21, 2023, expressed an unqualified opinion on those financial statements. ​ Basis for Opinion ​ The Company’s management is responsible for maintaining effective internal control over financial reporting and for its assessment of the effectiveness of internal control over financial reporting, included in the accompanying Management’s Report on Internal Control over Financial Reporting. Our responsibility is to express an opinion on the Company’s internal control over financial reporting based on our audit. We are a public accounting firm registered with the PCAOB and are required to be independent with respect to the Company in accordance with the U.S. federal securities laws and the applicable rules and regulations of the Securities and Exchange Commission and the PCAOB. ​ We conducted our audit in accordance with the standards of the PCAOB. Those standards require that we plan and perform the audit to obtain reasonable assurance about whether effective internal control over financial reporting was maintained in all material respects. Our audit included obtaining an understanding of internal control over financial reporting, assessing the risk that a material weakness exists, testing and evaluating the design and operating effectiveness of internal control based on the assessed risk, and performing such other procedures as we considered necessary in the circumstances. We believe that our audit provides a reasonable basis for our opinion. ​ Definition and Limitations of Internal Control over Financial Reporting ​ A company’s internal control over financial reporting is a process designed to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles. A company’s internal control over financial reporting includes those policies and procedures that (1) pertain to the maintenance of records that, in reasonable detail, accurately and fairly reflect the transactions and dispositions of the assets of the company; (2) provide reasonable assurance that transactions are recorded as necessary to permit preparation of financial statements in accordance with generally accepted accounting principles, and that receipts and expenditures of the company are being made only in accordance with authorizations of management and directors of the company; and (3) provide reasonable assurance regarding prevention or timely detection of unauthorized acquisition, use, or disposition of the company’s assets that could have a material effect on the financial statements. ​ Because of its inherent limitations, internal control over financial reporting may not prevent or detect misstatements. Also, projections of any evaluation of effectiveness to future periods are subject to the risk that controls may become inadequate because of changes in conditions, or that the degree of compliance with the policies or procedures may deteriorate. ​ /s/ DELOITTE & TOUCHE LLP ​ ​ ​ New York, New York ​ February 21, 2023 ​ ​ ​ ​ ​ ​ ​ 41 Table of Contents ​ iStar Inc. Consolidated Balance Sheets (In thousands, except per share data) (1) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ As of ​ ​ ​ December 31, ​ ​ 2022 2021 ​ ASSETS ​ ​ ​ Real estate ​ ​ ​ Real estate, at cost ​ $ 94,593 ​ $ 113,510 ​ Less: accumulated depreciation ​ ( 18,096 ) ​ ( 21,360 ) ​ Real estate, net ​ 76,497 ​ 92,150 ​ Real estate available and held for sale ​ 3,977 ​ 301 ​ Total real estate ​ 80,474 ​ 92,451 ​ Real estate and other assets available and held for sale and classified as discontinued operations (2) ​ ​ 2,939 ​ ​ 2,299,711 ​ Net investment in leases ​ ​ — ​ ​ 43,215 ​ Land and development, net ​ 232,014 ​ 286,810 ​ Loans receivable and other lending investments, net ( $ 925 and $ 4,769 of allowances as of December 31, 2022 and 2021, respectively) ​ 48,655 ​ 332,844 ​ Loans receivable held for sale ​ ​ 37,650 ​ ​ 43,215 ​ Other investments ​ 1,360,682 ​ 1,297,281 ​ Cash and cash equivalents ​ 1,442,269 ​ 339,601 ​ Accrued interest and operating lease income receivable, net ​ 1,132 ​ 1,813 ​ Deferred operating lease income receivable, net ​ 1,137 ​ 3,159 ​ Deferred expenses and other assets, net ​ 46,276 ​ 100,434 ​ Total assets ​ $ 3,253,228 ​ $ 4,840,534 ​ LIABILITIES AND EQUITY ​ ​ ​ Liabilities: ​ ​ ​ Accounts payable, accrued expenses and other liabilities ​ $ 143,477 ​ $ 236,732 ​ Liabilities associated with real estate held for sale and classified as discontinued operations (2) ​ ​ 333 ​ ​ 968,419 ​ Liabilities associated with properties held for sale ​ — ​ 3 ​ Debt obligations, net ​ 1,682,521 ​ 2,572,174 ​ Total liabilities ​ 1,826,331 ​ 3,777,328 ​ Commitments and contingencies (refer to Note 11) ​ ​ ​ Equity: ​ ​ ​ iStar Inc. shareholders' equity: ​ ​ ​ Preferred Stock Series D, G and I, liquidation preference $ 25.00 per share ​ 12 ​ 12 ​ Common Stock, $ 0.001 par value, 200,000 shares authorized, 86,724 and 68,870 shares issued and outstanding as of December 31, 2022 and 2021, respectively ​ 87 ​ 69 ​ Additional paid-in capital ​ 3,459,459 ​ 3,100,015 ​ Accumulated deficit ​ ( 2,053,270 ) ​ ( 2,227,213 ) ​ Accumulated other comprehensive income (loss) ​ 2,230 ​ ( 21,587 ) ​ Total iStar Inc. shareholders' equity ​ 1,408,518 ​ 851,296 ​ Noncontrolling interests ​ 18,379 ​ 211,910 ​ Total equity ​ 1,426,897 ​ 1,063,206 ​ Total liabilities and equity ​ $ 3,253,228 ​ $ 4,840,534 ​ (1) Refer to Note 2 for details on the Company’s consolidated variable interest entities (“VIEs”). Certain items have been reclassified to “Real estate and other assets available and held for sale and classified as discontinued operations” and “Liabilities associated with real estate held for sale and classified as discontinued operations” (refer to Note 3). (2) Refer to Note 3 – Net Lease Sale and Discontinued Operations. ​ ​ The accompanying notes are an integral part of the consolidated financial statements. ​ ​ 42 Table of Contents iStar Inc. Consolidated Statements of Operations (In thousands, except per share data) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ For the Years Ended December 31, ​ ​ 2022 2021 2020 Revenues: ​ ​ ​ ​ Operating lease income ​ $ 12,859 ​ $ 16,824 ​ $ 24,276 Interest income ​ 12,415 ​ 31,229 ​ 56,676 Interest income from sales-type leases ​ 869 ​ 1,215 ​ — Other income (1) ​ 70,155 ​ 70,259 ​ 78,445 Land development revenue ​ 61,753 ​ 189,103 ​ 164,702 Total revenues ​ 158,051 ​ 308,630 ​ 324,099 Costs and expenses: ​ ​ ​ Interest expense ​ 98,051 ​ 115,400 ​ 126,828 Real estate expense ​ 51,614 ​ 45,994 ​ 46,083 Land development cost of sales ​ 63,441 ​ 171,961 ​ 177,727 Depreciation and amortization ​ 5,470 ​ 7,072 ​ 7,327 General and administrative ​ 21,271 ​ 131,703 ​ 100,879 Provision for (recovery of) loan losses ​ 44,998 ​ ( 8,085 ) ​ 8,866 Impairment of assets ​ 15,109 ​ 678 ​ 5,791 Other expense ​ 8,913 ​ 8,114 ​ 569 Total costs and expenses ​ 308,867 ​ 472,837 ​ 474,070 Income from sales of real estate ​ 26,629 ​ 26,319 ​ 6,318 Loss from operations before earnings from equity method investments and other items ​ ( 124,187 ) ​ ( 137,888 ) ​ ( 143,653 ) Loss on early extinguishment of debt, net ​ ( 131,200 ) ​ — ​ ( 12,038 ) Earnings from equity method investments ​ 58,680 ​ 154,344 ​ 39,472 Net income (loss) from continuing operations before income taxes ​ ( 196,707 ) ​ 16,456 ​ ( 116,219 ) Income tax benefit (expense) ​ ( 567 ) ​ 118 ​ ( 89 ) Net income (loss) from continuing operations ​ ​ ( 197,274 ) ​ ​ 16,574 ​ ​ ( 116,308 ) Net income from discontinued operations (2) ​ 797,688 ​ 121,452 ​ 85,455 Net income (loss) ​ ​ 600,414 ​ ​ 138,026 ​ ​ ( 30,853 ) Net loss (income) from continuing operations attributable to noncontrolling interests ​ ( 37 ) ​ 75 ​ ( 337 ) Net (income) from discontinued operations attributable to noncontrolling interests ​ ​ ( 179,089 ) ​ ​ ( 5,620 ) ​ ​ ( 11,251 ) Net income (loss) attributable to iStar Inc. ​ 421,288 ​ 132,481 ​ ( 42,441 ) Preferred dividends ​ ( 23,496 ) ​ ( 23,496 ) ​ ( 23,496 ) Net income (loss) allocable to common shareholders ​ $ 397,792 ​ $ 108,985 ​ $ ( 65,937 ) Per common share data: ​ ​ ​ Net income (loss) allocable to common shareholders ​ ​ ​ Basic and diluted ​ $ 4.92 ​ $ 1.51 ​ $ ( 0.87 ) Net loss from continuing operations and allocable to common shareholders: ​ ​ ​ Basic and diluted ​ $ ( 2.74 ) ​ $ ( 0.10 ) ​ $ ( 1.85 ) Net income from discontinued operations and allocable to common shareholders: ​ ​ ​ Basic and diluted ​ $ 7.66 ​ $ 1.61 ​ $ 0.98 Weighted average number of common shares: ​ ​ ​ Basic and diluted ​ 80,722 ​ 71,831 ​ 75,684 (1) During the years ended December 31, 2022, 2021, and 2020, includes $ 20.7 million, $ 15.1 million and $ 12.9 million, respectively, of management fees from related parties. (2) Refer to Note 3 – Net Lease Sale and Discontinued Operations. ​ ​ The accompanying notes are an integral part of the consolidated financial statements. ​ 43 Table of Contents iStar Inc. Consolidated Statements of Comprehensive Income (Loss) (In thousands) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ For the Years Ended December 31, ​ ​ 2022 2021 2020 Net income (loss) ​ $ 600,414 ​ $ 138,026 ​ $ ( 30,853 ) Other comprehensive income (loss): ​ ​ ​ Reclassification of losses on cash flow hedges into earnings upon realization (1) ​ 7,737 ​ 24,566 ​ 8,075 Reclassification of losses on available-for-sale securities ​ ​ 386 ​ ​ — ​ ​ — Unrealized gains (losses) on available-for-sale securities ​ ( 4,623 ) ​ ( 357 ) ​ 1,838 Unrealized gains (losses) on cash flow hedges ​ 20,317 ​ 13,386 ​ ( 28,290 ) Other comprehensive income (loss) ​ 23,817 ​ 37,595 ​ ( 18,377 ) Comprehensive income (loss) ​ 624,231 ​ 175,621 ​ ( 49,230 ) Comprehensive (income) attributable to noncontrolling interests (2) ​ ( 179,126 ) ​ ( 21,860 ) ​ ( 7,184 ) Comprehensive income (loss) attributable to iStar Inc. ​ $ 445,105 ​ $ 153,761 ​ $ ( 56,414 ) (1) Reclassified to “Net income from discontinued operations” in the Company’s consolidated statements of operations are $ 22,623 and $ 6,974 for the years ended December 31, 2021 and 2020, respectively. Reclassified to “Earnings (losses) from equity method investments” in the Company’s consolidated statements of operations are $ 7,737 , $ 1,943 and $ 1,101 , respectively, for the years ended December 31, 2022, 2021 and 2020. (2) For the years ended December 31, 2022, 2021 and 2020, includes $ 179.1 million, $ 16.3 million and $ 6.8 million, respectively, of comprehensive income attributable to noncontrolling interests was from discontinued operations. ​ The accompanying notes are an integral part of the consolidated financial statements. ​ ​ 44 Table of Contents iStar Inc. Consolidated Statements of Changes in Equity (In thousands ) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ iStar Inc. Shareholders' Equity ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Accumulated ​ ​ ​ ​ ​ ​ ​ ​ ​ Common ​ ​ Additional ​ ​ Retained ​ ​ Other ​ ​ ​ ​ ​ ​ ​ ​ ​ Preferred ​ ​ Stock at ​ ​ Paid-In ​ ​ Earnings ​ ​ Comprehensive ​ ​ Noncontrolling ​ Total ​ ​ ​ Stock ​ ​ Par ​ ​ Capital ​ ​ (Deficit) ​ ​ Income (Loss) ​ ​ Interests ​ Equity Balance as of December 31, 2019 ​ $ 12 ​ $ 78 ​ $ 3,284,877 ​ $ ( 2,205,838 ) ​ $ ( 38,707 ) ​ $ 197,538 ​ $ 1,237,960 Impact from adoption of new accounting standards (refer to Note 3) ​ — ​ — ​ — ​ ( 12,382 ) ​ — ​ — ​ ( 12,382 ) Dividends declared—preferred ​ — ​ — ​ — ​ ( 23,496 ) ​ — ​ — ​ ( 23,496 ) Dividends declared—common ($ 0.43 per share) ​ — ​ — ​ — ​ ( 32,815 ) ​ — ​ — ​ ( 32,815 ) Issuance of stock/restricted stock unit amortization, net (1) ​ — ​ 1 ​ 4,060 ​ — ​ — ​ 3,363 ​ 7,424 Net income (loss) ​ — ​ — ​ — ​ ( 42,441 ) ​ — ​ 11,588 ​ ( 30,853 ) Change in accumulated other comprehensive income (loss) ​ — ​ — ​ — ​ — ​ ( 13,973 ) ​ ( 4,404 ) ​ ( 18,377 ) Repurchase of stock ​ — ​ ( 5 ) ​ ( 48,402 ) ​ — ​ — ​ — ​ ( 48,407 ) Contributions from noncontrolling interests ​ — ​ — ​ — ​ — ​ — ​ 496 ​ 496 Distributions to noncontrolling interests ​ — ​ — ​ — ​ — ​ — ​ ( 15,167 ) ​ ( 15,167 ) Balance as of December 31, 2020 ​ $ 12 ​ $ 74 ​ $ 3,240,535 ​ $ ( 2,316,972 ) ​ $ ( 52,680 ) ​ $ 193,414 ​ $ 1,064,383 Impact from adoption of new accounting standards (refer to Note 3) ​ — ​ — ​ ( 25,869 ) ​ 15,850 ​ — ​ — ​ ( 10,019 ) Dividends declared—preferred ​ — ​ — ​ — ​ ( 23,496 ) ​ — ​ — ​ ( 23,496 ) Dividends declared—common ($ 0.485 per share) ​ — ​ — ​ — ​ ( 35,076 ) ​ — ​ — ​ ( 35,076 ) Issuance of stock/restricted stock unit amortization, net (1) ​ — ​ — ​ 8,098 ​ — ​ — ​ 3,752 ​ 11,850 Net income ​ — ​ — ​ — ​ 132,481 ​ — ​ 5,545 ​ 138,026 Change in accumulated other comprehensive income (loss) ​ — ​ — ​ — ​ — ​ 31,093 ​ 10,670 ​ 41,763 Repurchase of stock ​ — ​ ( 5 ) ​ ( 122,414 ) ​ — ​ — ​ — ​ ( 122,419 ) Contributions from noncontrolling interests ​ — ​ — ​ — ​ — ​ — ​ 12,027 ​ 12,027 Distributions to noncontrolling interests ​ — ​ — ​ ( 335 ) ​ — ​ — ​ ( 13,424 ) ​ ( 13,759 ) Change to noncontrolling interest ​ ​ — ​ ​ — ​ ​ — ​ ​ — ​ ​ — ​ ​ ( 74 ) ​ ​ ( 74 ) Balance as of December 31, 2021 ​ $ 12 ​ $ 69 ​ $ 3,100,015 ​ $ ( 2,227,213 ) ​ $ ( 21,587 ) ​ $ 211,910 ​ $ 1,063,206 Dividends declared—preferred ​ — ​ — ​ — ​ ( 23,496 ) ​ — ​ — ​ ( 23,496 ) Dividends declared—common ($ 0.375 per share) ​ — ​ — ​ — ​ ( 31,839 ) ​ — ​ — ​ ( 31,839 ) Issuance of stock/restricted stock unit amortization, net (1) ​ — ​ 1 ​ 11,646 ​ — ​ — ​ 4,581 ​ 16,228 Net income ​ — ​ — ​ — ​ 421,288 ​ — ​ 179,126 ​ 600,414 Change in accumulated other comprehensive income (loss) ​ — ​ — ​ — ​ — ​ 18,380 ​ — ​ 18,380 Paid-in-kind dividend to common shareholders ($ 2.19 per share) ​ ​ — ​ ​ — ​ ​ — ​ ​ ( 192,010 ) ​ ​ 5,437 ​ ​ — ​ ​ ( 186,573 ) Issuance of common stock in connection with 3.125 % convertible notes (2) ​ — ​ 17 ​ 347,798 ​ — ​ — ​ — ​ 347,815 Contributions from noncontrolling interests ​ — ​ — ​ — ​ — ​ — ​ 7,893 ​ 7,893 Distributions to noncontrolling interests ​ — ​ — ​ — ​ — ​ — ​ ( 385,131 ) ​ ( 385,131 ) Balance as of December 31, 2022 ​ $ 12 ​ $ 87 ​ $ 3,459,459 ​ $ ( 2,053,270 ) ​ $ 2,230 ​ $ 18,379 ​ $ 1,426,897 (1) Net of payments for withholding taxes upon vesting of stock-based compensation. (2) Refer to Note 10 for details on the Company’s 3.125 % convertible notes. ​ ​ The accompanying notes are an integral part of the consolidated financial statements. ​ ​ 45 Table of Contents iStar Inc. Consolidated Statements of Cash Flows (In thousands) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ For the Years Ended December 31, ​ ​ 2022 2021 2020 Cash flows from operating activities: ​ ​ ​ ​ Net income (loss) ​ $ 600,414 ​ $ 138,026 ​ $ ( 30,853 ) Adjustments to reconcile net income (loss) to cash flows from operating activities: ​ ​ ​ (Recovery of) provision for loan losses ​ 44,998 ​ ( 9,235 ) ​ 9,052 (Recovery of) provision for losses on net investment in leases ​ — ​ ( 10,872 ) ​ 1,760 Impairment of assets ​ 16,600 ​ 2,965 ​ 7,827 Depreciation and amortization ​ 5,470 ​ 59,294 ​ 58,092 Non-cash interest income from sales-type leases ​ ( 1,748 ) ​ ( 25,054 ) ​ ( 24,969 ) Stock-based compensation expense ​ ( 27,664 ) ​ 69,261 ​ 39,354 Amortization of discounts/premiums and deferred financing costs on debt obligations, net ​ 9,322 ​ 8,572 ​ 13,328 Amortization of discounts/premiums and deferred interest on loans, net ​ ( 6,859 ) ​ ( 14,481 ) ​ ( 30,738 ) Deferred interest on loans received ​ 8,725 ​ 27,526 ​ 20,661 Selling profit from sales-type leases ​ — ​ ( 25,034 ) ​ — Earnings from equity method investments ​ ( 185,809 ) ​ ( 162,467 ) ​ ( 42,126 ) Distributions from operations of other investments ​ 158,427 ​ 51,588 ​ 24,826 Deferred operating lease income ​ ( 2,055 ) ​ ( 11,310 ) ​ ( 14,052 ) Income from sales of real estate ​ ( 710,367 ) ​ ( 34,794 ) ​ ( 6,318 ) Land development revenue in excess of cost of sales ​ 1,688 ​ ( 17,142 ) ​ 13,025 Loss on early extinguishment of debt, net ​ 172,608 ​ — ​ 12,038 Other operating activities, net ​ ( 13,043 ) ​ 720 ​ ( 19,496 ) Changes in assets and liabilities: ​ ​ ​ ​ ​ Origination and fundings of loans receivable held for sale, net ​ ​ — ​ ​ ( 59,624 ) ​ ​ — Proceeds from sale of loans receivable held for sale ​ ​ 43,536 ​ ​ — ​ ​ — Changes in accrued interest and operating lease income receivable ​ 2,252 ​ 5,493 ​ ( 2,311 ) Changes in deferred expenses and other assets, net ​ ( 17,562 ) ​ ( 11,995 ) ​ ( 5,351 ) Changes in accounts payable, accrued expenses and other liabilities ​ ( 51,266 ) ​ ( 1,764 ) ​ ( 1,863 ) Cash flows provided by (used in) operating activities ​ 47,667 ​ ( 20,327 ) ​ 21,886 Cash flows from investing activities: ​ ​ ​ Originations and fundings of loans receivable, net ​ ( 6,740 ) ​ ( 75,250 ) ​ ( 119,368 ) Capital expenditures on real estate assets ​ ( 1,178 ) ​ ( 6,762 ) ​ ( 15,798 ) Capital expenditures on land and development assets ​ ( 21,875 ) ​ ( 23,929 ) ​ ( 40,954 ) Acquisitions of real estate, net investments in leases and land assets ​ ( 40,273 ) ​ ( 42,652 ) ​ — Repayments of and principal collections on loans receivable and other lending investments, net ​ 129,109 ​ 270,393 ​ 208,240 Net proceeds from sales of loans receivable ​ 128,585 ​ 122,609 ​ 11,000 Net proceeds from sales of real estate ​ 2,021,821 ​ 157,258 ​ 48,415 Net proceeds from sales of land and development assets ​ 59,946 ​ 182,723 ​ 161,063 Net proceeds from sales of other investments ​ ​ 608,238 ​ ​ 111,429 ​ ​ — Distributions from other investments ​ 175,398 ​ 35,036 ​ 39,871 Contributions to and acquisition of interest in other investments ​ ( 274,544 ) ​ ( 216,997 ) ​ ( 260,121 ) Other investing activities, net ​ 9,325 ​ 158 ​ ( 1,169 ) Cash flows provided by investing activities ​ 2,787,812 ​ 514,016 ​ 31,179 Cash flows from financing activities: ​ ​ ​ Borrowings from debt obligations ​ 50,000 ​ 25,000 ​ 802,913 Repayments and repurchases of debt obligations ​ ( 1,154,033 ) ​ ( 73,559 ) ​ ( 913,501 ) Purchase of marketable securities in connection with the defeasance of mortgage notes payable ​ ( 252,571 ) ​ ​ — ​ ​ — Preferred dividends paid ​ ( 23,496 ) ​ ( 23,496 ) ​ ( 23,496 ) Common dividends paid ​ ( 30,224 ) ​ ( 34,783 ) ​ ( 32,664 ) Repurchase of stock ​ — ​ ( 122,618 ) ​ ( 54,565 ) Payments for deferred financing costs ​ ( 25 ) ​ ( 14,288 ) ​ ( 7,711 ) Payments for withholding taxes upon vesting of stock-based compensation ​ ( 10,567 ) ​ ( 4,093 ) ​ ( 2,716 ) Contributions from noncontrolling interests ​ 7,893 ​ 11,127 ​ 496 Distributions to noncontrolling interests ​ ( 351,005 ) ​ ( 13,425 ) ​ ( 15,167 ) Payments for debt prepayment or extinguishment costs ​ ( 16,676 ) ​ — ​ ( 8,567 ) Cash flows used in financing activities ​ ( 1,780,704 ) ​ ( 250,135 ) ​ ( 254,978 ) Effect of exchange rate changes on cash ​ ( 79 ) ​ ( 124 ) ​ 273 Changes in cash, cash equivalents and restricted cash ​ 1,054,696 ​ 243,430 ​ ( 201,640 ) Cash, cash equivalents and restricted cash at beginning of period ​ 393,996 ​ 150,566 ​ 352,206 Cash, cash equivalents and restricted cash at end of period ​ $ 1,448,692 ​ $ 393,996 ​ $ 150,566 Supplemental disclosure of cash flow information: ​ ​ ​ Cash paid during the period for interest, net of amount capitalized ​ $ 103,068 ​ $ 143,451 ​ $ 142,453 46 Table of Contents iStar Inc. Consolidated Statements of Cash Flows (In thousands) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ For the Years Ended December 31, ​ ​ 2022 2021 2020 Reconciliation of cash and cash equivalents and restricted cash presented on the consolidated statements of cash flows ​ ​ ​ ​ ​ ​ ​ ​ ​ Cash and cash equivalents ​ $ 1,442,269 ​ $ 339,601 ​ $ 98,633 Restricted cash included in deferred expenses and other assets, net ​ ​ 6,423 ​ ​ 54,395 ​ ​ 51,933 Total cash and cash equivalents and restricted cash ​ $ 1,448,692 ​ $ 393,996 ​ $ 150,566 Supplemental disclosure of non-cash investing and financing activity: ​ ​ ​ ​ Fundings and (repayments) of loan receivables and loan participations, net ​ $ — ​ $ ( 42,501 ) ​ $ 6,720 Accounts payable for capital expenditures on land and development and real estate assets ​ ​ 828 ​ ​ 3,085 ​ 7,604 Contributions to other investments ​ ​ — ​ ​ 1,000 ​ ​ — Sales-type lease origination ​ — ​ 41,000 ​ — Distributions to noncontrolling interests ​ ​ 34,467 ​ ​ — ​ ​ — Defeasance of mortgage notes payable ​ ​ 230,452 ​ ​ — ​ ​ — Marketable securities transferred in connection with the defeasance of mortgage notes payable ​ ​ 252,571 ​ ​ — ​ ​ — Settlement of senior unsecured notes (refer to Note 10) ​ 218,945 ​ — ​ — Increase in net lease assets upon consolidation of equity method investment ​ ​ — ​ ​ 45,313 ​ ​ — Increase in debt obligations upon consolidation of equity method investment ​ ​ — ​ ​ 44,672 ​ ​ — Non-cash proceeds from sale of land and development asset ​ ​ — ​ ​ 1,200 ​ ​ — Financing provided on sales of real estate ​ ​ — ​ ​ 8,000 ​ ​ — Accrued finance costs ​ — ​ — ​ 115 Accrued repurchase of stock ​ — ​ — ​ 200 Transfer of loan receivable to loans receivable held for sale (refer to Note 7) ​ ​ 37,650 ​ ​ — ​ ​ — Payment of non-cash dividend (refer to Note 13) ​ ​ 192,010 ​ ​ — ​ ​ — Assumption of mortgage by third party ​ 62,825 ​ — ​ — ​ The accompanying notes are an integral part of the consolidated financial statements. ​ ​ 47 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Note 1—Business and Organization Business —iStar Inc. (the “Company”) finances, invests in and develops real estate and real estate related projects as part of its fully-integrated investment platform. The Company also manages entities focused on ground lease investments (refer to Note 8). The Company has invested capital over the past two decades and is structured as a real estate investment trust (“REIT”) with a diversified portfolio focused on larger assets located in major metropolitan markets. The Company’s primary reportable business segments are net lease (refer to Note 3 - Net Lease Sale and Discontinued Operations), real estate finance, operating properties and land and development (refer to Note 17). Organization —The Company began its business in 1993 through the management of private investment funds and became publicly traded in 1998. Since that time, the Company has grown through the origination of new investments and corporate acquisitions. Merger with Safehold Inc. —On August 10, 2022, the Company entered into an Agreement and Plan of Merger (the “ Merger Agreement ”) with Safehold Inc. (“SAFE”). The Merger Agreement provides that, subject to the terms and conditions thereof, SAFE will merge with and into the Company (the “Merger”). The surviving company of the Merger will be named Safehold Inc. (“ New SAFE ”) and its shares of common stock will trade on the New York Stock Exchange under the symbol “SAFE.” The Company expects that the Merger will close in the first quarter or second quarter of 2023. ​ As discussed further below, shortly before the closing of the Merger, the Company intends to separate its remaining legacy non-ground lease assets and businesses into a separate public company (“ Star Holdings ”) by distributing to the Company’s stockholders, on a pro rata basis, the issued and outstanding equity interests of Star Holdings (the “ Spin-Off ”). ​ Conditions to the Merger The consummation of the Merger is subject to the satisfaction or waiver of certain closing conditions, including: (i) the approval of the Company’s stockholders, (ii) the approval of SAFE’s stockholders, (iii) completion of the Spin-Off, (iv) the approval of the shares of STAR Common Stock to be issued in the Merger for listing on the NYSE, (v) the absence of any temporary restraining order, injunction or other order of any court of competent jurisdiction or other legal restraint or prohibition preventing the consummation of the reverse stock split or the Merger, (vi) generation of certain cash proceeds, (vii) the receipt of certain tax opinions by the Company and SAFE that the Merger will qualify as a reorganization under the Internal Revenue Code and that the Company and SAFE each qualifies as a REIT for federal income tax purposes, (viii) the accuracy of certain representations and warranties of the Company and SAFE contained in the Merger Agreement and the compliance by the parties with the covenants contained in the Merger Agreement (subject to customary materiality qualifiers), and (ix) other conditions specified in the Merger Agreement. ​ Conditions to the Spin-Off ​ Completion of the Spin-Off is subject to: (i) completion of the documents for the Spin-Off related financings; (ii) the satisfaction or waiver of relevant conditions to the consummation of the Merger; (iii) effectiveness of a registration statement on Securities and Exchange Commission (“SEC”) Form 10; (iv) the absence of an injunction or law preventing the consummation of the Spin-Off, the distribution and the transactions related thereto; and (v) other customary closing conditions. ​ Other Merger related transactions ​ The Company has entered into an agreement (the “ MSD Stock Purchase Agreement ”) with MSD Partners, L.P. (“ MSD Partners ”) and SAFE under which the Company has agreed to sell and MSD Partners has agreed to buy 5,405,406 shares of the SAFE’s common stock owned by the Company for $ 200.0 million (the “ MSD Stock Purchase ”) shortly before the closing of the Merger. If the Merger Agreement is terminated for any reason, the parties’ obligations to consummate the purchase and sale will also terminate. In addition to customary closing conditions, MSD Partners’ obligations to purchase SAFE’s common stock owned by the Company are subject to the condition that the closing of the MSD Caret Purchase (as defined below) will take place substantially concurrently with the closing of the MSD Stock 48 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Purchase. Upon closing of the transaction, MSD Partners will have a right to designate an observer to the board of directors of New SAFE, a preemptive right on future equity issuances (subject to certain exceptions) and registration rights. MSD Partners will be subject to a customary standstill and certain restrictions on sales of its New SAFE Common Stock. MSD Partners has also subscribed to purchase 100,000 Caret units from SAFE for an aggregate purchase price of $ 20.0 million (the “ MSD Caret Purchase ”), conditioned on the closing of the Spin-Off and the Merger. MSD Partners’ obligations to purchase the Caret units are also subject to the closing of the MSD Stock Purchase and the implementation by SAFE of certain changes to its Caret program. ​ Star Holdings will be capitalized in part with an 8.0 %, four-year term loan from New SAFE having an initial principal amount of $ 100.0 million or such other amount as the parties may agree prior to the closing of the Merger, as well as up to $ 140.0 million of bank debt from Morgan Stanley Bank, N.A. which will be secured by $ 400.0 million in shares of SAFE common stock. New SAFE will enter into a management agreement with Star Holdings, under which it will continue to operate and pursue the orderly monetization of Star Holding’s assets. Star Holdings will pay to New SAFE an annual management fee of $ 25.0 million in year one, $ 15.0 million in year two, $ 10.0 million in year three and $ 5.0 million in year four and 2.0 % of the gross book value of Star Holding's assets, excluding shares of SAFE common stock, for each annual term thereafter. New SAFE and Star Holdings will also enter into a governance agreement that will place certain restrictions on the transfer and voting of the shares of New SAFE owned by Star Holdings, and a registration rights agreement under which New SAFE will agree to register such shares for resale in accordance with applicable securities laws. ​ The Company and SAFE have entered into a voting agreement pursuant to which the Company has agreed vote its shares representing 41.9 % of the outstanding SAFE Common Stock to approve the Merger and take certain other actions, including voting against any alternative acquisition proposal or other proposal which could reasonably be expected to materially delay, postpone or materially adversely affect the consummation of the transactions contemplated by the Merger Agreement. In accordance with the terms of the existing stockholders’ agreement between SAFE and the Company, the remainder of the SAFE Common Stock owned by the Company will be voted in the same manner and proportion as the votes cast by the remaining shareholders of SAFE. The voting agreement and the obligations thereunder terminate upon the termination of the Merger Agreement in accordance with its terms. ​ As noted above, the Merger and related transactions are subject to a number of conditions, several of which are outside the Company's control; therefore, there can be no assurance that the Merger and related transactions will occur within the time frame currently expected by the parties, or at all. The foregoing descriptions of the Merger and the Merger Agreement and the related transactions and agreements do not purport to be complete and are subject to, and qualified in their entirety by, the full text of such agreements. Please see the Company's filings with the Securities and Exchange Commission for additional information, including copies of such agreements. ​ The Company has covenanted to redeem all of its outstanding preferred stock at the liquidation preference per share plus accrued and unpaid dividends and to retire all of its remaining senior unsecured notes in connection with the Merger. The Company’s trust preferred securities will remain outstanding at New SAFE. Note 2—Basis of Presentation and Principles of Consolidation Basis of Presentation —The accompanying consolidated financial statements have been prepared in conformity with generally accepted accounting principles in the United States of America (“GAAP”). The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the dates of the financial statements and the reported amounts of revenues and expenses during the reporting periods. Actual results could differ from those estimates. Principles of Consolidation —The consolidated financial statements include the financial statements of the Company, its wholly owned subsidiaries, controlled partnerships and VIEs for which the Company is the primary beneficiary. All intercompany balances and transactions have been eliminated in consolidation. The Company’s 49 Table of Contents iStar Inc. Notes to Consolidated Financial Statements involvement with VIEs affects its financial performance and cash flows primarily through amounts recorded in “Net income from discontinued operations,” “Operating lease income,” “Interest income,” “Earnings from equity method investments,” “Real estate expense” and “Interest expense” in the Company’s consolidated statements of operations. The Company has provided no financial support to those VIEs that it was not previously contractually required to provide. Consolidated VIEs —The Company consolidates VIEs for which it is considered the primary beneficiary. The liabilities of these VIEs are non-recourse to the Company and can only be satisfied from each VIE’s respective assets. The Company did not have any unfunded commitments related to consolidated VIEs as of December 31, 2022. The following table presents the assets and liabilities of the Company’s consolidated VIEs as of December 31, 2022 and 2021 ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ As of ​ December 31, 2022 December 31, 2021 ASSETS ​ ​ ​ Real estate ​ ​ ​ Real estate, at cost ​ $ 94,159 ​ $ 93,477 Less: accumulated depreciation ​ ( 18,033 ) ​ ( 14,987 ) Real estate, net ​ 76,126 ​ 78,490 Real estate and other assets available and held for sale and classified as discontinued operations ​ ​ — ​ ​ 886,845 Land and development, net ​ 128,717 ​ 176,833 Cash and cash equivalents ​ 11,886 ​ 23,908 Deferred operating lease income receivable, net ​ 6 ​ 3 Deferred expenses and other assets, net ​ 6,921 ​ 5,001 Total assets ​ $ 223,656 ​ $ 1,171,081 LIABILITIES ​ ​ Accounts payable, accrued expenses and other liabilities ​ $ 24,406 ​ $ 24,744 Liabilities associated with real estate held for sale and classified as discontinued operations ​ ​ 146 ​ ​ 493,739 Total liabilities ​ 24,552 ​ 518,483 ​ Unconsolidated VIEs —The Company has investments in VIEs where it is not the primary beneficiary, and accordingly, the VIEs have not been consolidated in the Company’s consolidated financial statements. As of December 31, 2022, the Company’s maximum exposure to loss from these investments does not exceed the sum of the $ 32.1 million carrying value of the investments, which are classified in "Other investments" on the Company’s consolidated balance sheets. Note 3—Summary of Significant Accounting Policies Significant Accounting Policies Real estate and land and development— Real estate and land and development assets are recorded at cost less accumulated depreciation and amortization, as follows: Capitalization and depreciation— Certain improvements and replacements are capitalized when they extend the useful life of the asset. For real estate projects, the Company begins to capitalize qualifying development and construction costs, including interest, real estate taxes, compensation and certain other carrying costs incurred which are specifically identifiable to a development project once activities necessary to get the asset ready for its intended use have commenced. If specific allocation of costs is not practicable, the Company will allocate costs based on relative fair value prior to construction or relative sales value, relative size or other methods as appropriate during construction. The Company’s policy for interest capitalization on qualifying real estate assets is to use the average amount of accumulated expenditures during the period the asset is being prepared for its intended use, which is typically when physical construction commences, and a capitalization rate which is derived from specific borrowings on the qualifying asset or the Company’s corporate borrowing rate in the absence of specific borrowings. The Company ceases capitalization on the portions substantially completed and ready for their intended use. Repairs and maintenance costs are expensed as incurred. Depreciation is computed using the straight-line method of cost recovery over the estimated useful life, which is generally 40 years for 50 Table of Contents iStar Inc. Notes to Consolidated Financial Statements facilities, five years for furniture and equipment, the shorter of the remaining lease term or expected life for tenant improvements and the remaining useful life of the facility for facility improvements. Purchase price allocation— The Company’s acquisition of properties is generally accounted for as an acquisition of assets. For asset acquisitions, the Company recognizes and measures identifiable assets acquired, liabilities assumed and any noncontrolling interest in the acquiree based on their relative fair values and acquisition-related costs are capitalized and recorded in "Real estate, net" on the Company’s consolidated balance sheets. The Company accounts for its acquisition of properties by recording the purchase price of tangible and intangible assets and liabilities acquired based on their relative fair values. The value of the tangible assets, consisting of land, buildings, building improvements and tenant improvements is determined as if these assets are vacant. Intangible assets may include the value of lease incentive assets, above-market leases and in-place leases which are each recorded at their relative fair values and included in “Deferred expenses and other assets, net” on the Company’s consolidated balance sheets. Intangible liabilities may include the value of below-market leases, which are recorded at their relative fair values and included in “Accounts payable, accrued expenses and other liabilities” on the Company’s consolidated balance sheets. In-place leases are amortized over the remaining non-cancelable term and the amortization expense is included in "Depreciation and amortization" in the Company’s consolidated statements of operations. Lease incentive assets and above-market (or below-market) lease value is amortized as a reduction of (or, increase to) operating lease income over the remaining non-cancelable term of each lease plus any renewal periods with fixed rental terms that are considered to be below-market. The Company may also engage in sale/leaseback transactions and execute leases with the occupant simultaneously with the purchase of the asset. These transactions are accounted for as asset acquisitions. Impairments— The Company reviews real estate assets to be held for use and land and development assets for impairment in value whenever events or changes in circumstances indicate that the carrying amount of such assets may not be recoverable. The value of a long-lived asset held for use and land and development assets are impaired only if management’s estimate of the aggregate future cash flows (undiscounted and without interest charges) to be generated by the asset (taking into account the anticipated holding period of the asset) is less than the carrying value. Such estimate of cash flows considers factors such as expected future operating income trends, as well as the effects of demand, competition and other economic factors. To the extent impairment has occurred, the loss will be measured as the excess of the carrying amount of the property over the estimated fair value of the asset and reflected as an adjustment to the basis of the asset. Impairments of real estate assets and land and development assets are recorded in "Impairment of assets" in the Company’s consolidated statements of operations. Real estate available and held for sale— The Company reports real estate assets to be sold at the lower of their carrying amount or estimated fair value less costs to sell and classifies them as “Real estate available and held for sale” on the Company’s consolidated balance sheets. If the estimated fair value less costs to sell is less than the carrying value, the difference will be recorded as an impairment charge. Impairment for real estate assets disposed of or classified as held for sale are included in "Impairment of assets" in the Company’s consolidated statements of operations. Once a real estate asset is classified as held for sale, depreciation expense is no longer recorded. The Company classifies its real estate assets as held for sale in the period in which all of the following conditions are met: (i) the Company commits to a plan and has the authority to sell the asset; (ii) the asset is available for sale in its current condition; (iii) the Company has initiated an active marketing plan to locate a buyer for the asset; (iv) the sale of the asset is both probable and expected to qualify for full sales recognition within a period of 12 months; (v) the asset is being actively marketed for sale at a price that is reflective of its current fair value; and (vi) the Company does not anticipate changes to its plan to sell the asset. Assets held for sale may qualify as a discontinued operation if certain conditions exist (refer to Net Lease Sale and Discontinued Operations). If circumstances arise that were previously considered unlikely and, as a result the Company decides not to sell a property previously classified as held for sale, the property is reclassified as held and used and included in "Real estate, net" on the Company’s consolidated balance sheets. The Company measures and records a property that is reclassified as held and used at the lower of: (i) its carrying amount before the property was classified as held for sale, adjusted for any depreciation expense that would have been recognized had the property been continuously classified as held and used; or (ii) the estimated fair value at the date of the subsequent decision not to sell. 51 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Dispositions— Gains or losses on the sale of real estate assets, including residential property, are recognized in accordance with Accounting Standards Codification ("ASC") 610-20 , Gains and Losses from the Derecognition of Nonfinancial Assets. The Company primarily uses specific identification and the relative sales value method to allocate costs. Gains on sales of real estate are included in "Income from sales of real estate" or “Net income from discontinued operations” in the Company’s consolidated statements of operations. Net Investment in Leases —Net investment in leases are recognized when the Company’s leases qualify as sales-type leases. The net investment in leases is initially measured at the present value of the fixed and determinable lease payments, including any guaranteed or unguaranteed estimated residual value of the asset at the end of the lease, discounted at the rate implicit in the lease. Acquisition-related costs are capitalized and recorded in "Net Investment in Leases" on the Company’s consolidated balance sheets. If a lease qualifies as a sales-type lease, it is further evaluated to determine whether the transaction is considered a sale leaseback transaction. If the sales-type lease does not qualify as a sale leaseback transaction, the lease is considered a financing receivable and is recognized in accordance with ASC 310 - Receivables (refer to Note 5) and recorded in "Loans receivable and other lending investments, net" on the Company’s consolidated balance sheets. Loans receivable and other lending investments, net — Loans receivable and other lending investments, net includes the following investments: senior mortgages, corporate/partnership loans, subordinate mortgages, preferred equity investments and debt securities. Management considers nearly all of its loans to be held-for-investment, although certain investments may be classified as held-for-sale or available-for-sale. Loans receivable classified as held-for-investment and debt securities classified as held-to-maturity are reported at their outstanding unpaid principal balance net of any unamortized acquisition premiums or discounts and unamortized deferred loan costs or fees. These loans and debt securities could also include accrued and paid-in-kind interest and accrued exit fees that the Company determines are probable of being collected. Debt securities classified as available-for-sale are reported at fair value with unrealized gains and losses recorded in "Accumulated other comprehensive income (loss)" on the Company’s consolidated balance sheets. Realized gains on the sale of available-for-sale securities are recorded in “Other income” in the Company’s consolidated statements of operations. ​ Loans receivable and other lending investments designated for sale are classified as held-for-sale and are carried at lower of amortized cost or estimated fair value. The amount by which carrying value exceeds fair value is recorded as a valuation allowance. Subsequent changes in the valuation allowance are included in the determination of net income (loss) in the period in which the change occurs. The Company may acquire properties through foreclosure or by deed-in-lieu of foreclosure in full or partial satisfaction of non-performing loans. Based on the Company’s strategic plan to realize the maximum value from the collateral received, property is classified as "Land and development, net," "Real estate, net" or "Real estate available and held for sale" at its estimated fair value when title to the property is obtained. Any excess of the carrying value of the loan over the estimated fair value of the property (less costs to sell for assets held for sale) is charged-off against the allowance for loan losses as of the date of foreclosure. Equity method investments — Equity interests are accounted for pursuant to the equity method of accounting if the Company can significantly influence the operating and financial policies of an investee. The Company’s periodic share of earnings and losses in equity method investees is included in "Earnings from equity method investments" in the consolidated statements of operations. Equity method investments are included in "Other investments" on the Company’s consolidated balance sheets. The Company also has equity interests that are not accounted for pursuant to the equity method of accounting. These equity interests are carried at cost, plus or minus any changes in value identified through observable comparable price changes in transactions in identical or similar investments of the same entity. The changes in fair value for these investments are included in "Other income" in the consolidated statements of operations. The Company periodically reviews equity method investments for impairment in value whenever events or changes in circumstances indicate that the carrying amount of such investments may not be recoverable. The Company will record an impairment charge to the extent that the estimated fair value of an investment is less than its carrying value and the Company determines the impairment is other-than-temporary. Impairment charges are recorded in "Earnings from equity method investments" in the Company’s consolidated statements of operations. 52 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Cash and cash equivalents — Cash and cash equivalents include cash held in banks or invested in money market funds with original maturity terms of less than 90 days. Restricted cash — Restricted cash represents amounts required to be maintained under certain of the Company’s debt obligations, loans, leasing, land development and derivative transactions. Restricted cash is included in "Deferred expenses and other assets, net" on the Company’s consolidated balance sheets. Variable interest entities — The Company evaluates its investments and other contractual arrangements to determine if they constitute variable interests in a VIE. A VIE is an entity where a controlling financial interest is achieved through means other than voting rights. A VIE is consolidated by the primary beneficiary, which is the party that has the power to direct matters that most significantly impact the activities of the VIE and has the obligation to absorb losses or the right to receive benefits of the VIE that could potentially be significant to the VIE. This overall consolidation assessment includes a review of, among other factors, which interests create or absorb variability, contractual terms, the key decision making powers, their impact on the VIE’s economic performance, and related party relationships. Where qualitative assessment is not conclusive, the Company performs a quantitative analysis. The Company reassesses its evaluation of the primary beneficiary of a VIE on an ongoing basis and assesses its evaluation of an entity as a VIE upon certain reconsideration events. Deferred expenses and other assets / Accounts payable, accrued expenses and other liabilities — Deferred expenses and other assets include right-of-use lease assets, prepaid expenses, certain non-tenant receivables, leasing costs, lease incentives and financing fees associated with revolving-debt arrangements. Financing fees associated with other debt obligations are recorded as a reduction of the carrying value of "Debt obligations, net" on the Company’s consolidated balance sheets. Lease incentives and leasing costs that include brokerage, legal and other costs are amortized over the life of the respective leases and presented as an operating activity in the Company’s consolidated statements of cash flows. External fees and costs incurred to obtain long-term debt financing have been deferred and are amortized over the term of the respective borrowing using the effective interest method. Amortization of leasing costs is included in "Depreciation and amortization" and amortization of deferred financing fees is included in "Interest expense" in the Company’s consolidated statements of operations. The Company, as lessee, records right-of-use operating lease assets in "Deferred expenses and other assets," operating lease liabilities in "Accounts payable, accrued expenses and other liabilities," right-of-use finance lease assets in “Finance lease right of use assets” and finance lease liabilities in “Finance lease liabilities” on its consolidated balance sheets, all measured at the present value of the fixed and determinable lease payments. Some of the Company’s lease agreements include extension options, which are not included in the lease payments unless the extensions are reasonably certain to be exercised. For operating leases, the Company recognizes a single lease cost for office leases in "General and administrative" and a single lease cost for ground leases in "Real estate expense" in the consolidated statements of operations, calculated so that the cost of the lease is allocated generally on a straight-line basis over the term of the lease, and classifies all cash payments within operating activities in the consolidated statements of cash flows. For finance leases, the Company recognizes amortization of the right-of-use assets on a straight-line basis over the term of the lease in "Depreciation and amortization" and interest expense on the lease liability using the effective interest method in "Interest expense" in the consolidated statements of operations. Repayments of the principal portion of the finance lease liability are classified within financing activities in the consolidated statements of cash flows and payments of interest on a finance lease liability are classified within operating activities in the consolidated statement of cash flows. Identified intangible assets and liabilities — Upon the acquisition of a business or an asset, the Company records intangible assets or liabilities acquired at their relative fair values and determines whether such intangible assets or liabilities have finite or indefinite lives. As of December 31, 2022, all such intangible assets and liabilities acquired by the Company have finite lives. Intangible assets are included in "Deferred expenses and other assets, net" and intangible liabilities are included in "Accounts payable, accrued expenses and other liabilities" on the Company’s consolidated balance sheets. The Company amortizes finite lived intangible assets and liabilities based on the period over which the assets are expected to contribute directly or indirectly to the future cash flows of the business acquired. The Company reviews finite lived intangible assets for impairment whenever events or changes in circumstances indicate that their carrying amount may not be recoverable. If the Company determines the carrying value of an intangible asset is not recoverable it will record an impairment charge to the extent its carrying value exceeds its estimated fair value. 53 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Impairments of intangible assets are recorded in "Impairment of assets" in the Company’s consolidated statements of operations. Revenue recognition — The Company’s revenue recognition policies are as follows: Operating lease income: For the Company’s leases classified as operating leases, operating lease income is recognized on the straight-line method of accounting generally from the later of the date the lessee takes possession of the space or the space is ready for its intended use. If the Company acquires a facility subject to an existing operating lease, the Company will recognize operating lease income on the straight-line method beginning on the date of acquisition. Accordingly, contractual lease payment increases are recognized evenly over the term of the lease. The periodic difference between lease revenue recognized under this method and contractual lease payment terms is recorded as "Deferred operating lease income receivable, net" on the Company’s consolidated balance sheets. The Company also recognizes revenue from certain tenant leases for reimbursements of all or a portion of operating expenses, including common area costs, insurance, utilities and real estate taxes of the respective property. This revenue is accrued in the same periods as the expense is incurred and is recorded as “Operating lease income” in the Company’s consolidated statements of operations. Revenue is also recorded from certain tenant leases that is contingent upon tenant sales exceeding defined thresholds. These rents are recognized only after the defined threshold has been met for the period. The Company moves to cash basis operating lease income recognition in the period in which collectability of all lease payments is no longer considered probable. At such time, any operating lease receivable or deferred operating lease income receivable balance will be written off. If and when lease payments that were previously not considered probable of collection become probable, the Company will move back to the straight-line method of income recognition and record an adjustment to operating lease income in that period as if the lease was always on the straight-line method of income recognition. Interest Income: Interest income on loans receivable and financing receivables is recognized on an accrual basis using the interest method. On occasion, the Company may acquire loans at premiums or discounts. These discounts and premiums in addition to any deferred costs or fees, are typically amortized over the contractual term of the loan using the interest method. Exit fees are also recognized over the lives of the related loans as a yield adjustment, if management believes it is probable that such amounts will be received. If loans with premiums, discounts, loan origination or exit fees are prepaid, the Company immediately recognizes the unamortized portion, which is included in "Other income" or "Other expense" in the Company’s consolidated statements of operations. The Company considers a loan to be non-performing and places it on non-accrual status at such time as: (1) interest payments become 90 days delinquent; (2) it has a maturity default; or (3) management determines it is probable that it will be unable to collect all amounts due according to the contractual terms of the loan. While on non-accrual status, based on the Company’s judgment as to collectability of principal, loans are either accounted for on a cash basis, where interest income is recognized only upon actual receipt of cash, or on a cost-recovery basis, where all cash receipts reduce a loan’s carrying value. Non-accrual loans are returned to accrual status when a loan has become contractually current and management believes all amounts contractually owed will be received. Certain of the Company’s loans contractually provide for accrual of interest at specified rates that differ from current payment terms. Interest is recognized on such loans at the accrual rate subject to management’s determination that accrued interest and outstanding principal are ultimately collectible, based on the underlying collateral and operations of the borrower. Certain of the Company’s loan investments provide for additional interest based on the borrower’s operating cash flow or appreciation of the underlying collateral. Such amounts are considered contingent interest and are reflected as interest income only upon receipt of cash. 54 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Interest Income from Sales-Type Leases: Interest income from sales-type leases is recognized in "Interest income from sales-type leases" in the Company’s consolidated statements of operations under the effective interest method. The effective interest method produces a constant yield on the net investment in the lease over the term of the lease. Rent payments that are not fixed and determinable at lease inception, such as percentage rent and CPI adjustments, are not included in the effective interest method calculation and are recognized in the Company’s consolidated statements of operations in the period earned. Other income: Other income includes mark-to-market gains on equity investments, management fees, other ancillary income from our operating properties, land and development projects and loan portfolio and revenues from hotel operations, which are recognized when rooms are occupied and the related services are provided. Hotel revenues include room sales, food and beverage sales, parking, telephone, spa services and gift shop sales. Other ancillary income could include gains from sales of loans, loan prepayment fees, yield maintenance payments, lease termination fees and other ancillary income. Land development revenue and cost of sales: Land development revenue includes lot and parcel sales from wholly-owned properties and is recognized for full profit recognition upon closing of the sale transactions, when the profit is determinable, the earnings process is virtually complete, the parties are bound by the terms of the contract, all consideration has been exchanged, any permanent financing for which the seller is responsible has been arranged and all conditions for closing have been performed. The Company primarily uses specific identification and the relative sales value method to allocate costs. Allowance for loan losses and net investment in leases — The Company performs quarterly a comprehensive analysis of its loan and sales-type lease portfolios and assigns risk ratings that incorporate management’s current judgments about credit quality based on all known and relevant internal and external factors that may affect collectability. The Company considers, among other things, payment status, lien position, borrower or tenant financial resources and investment collateral, collateral type, project economics and geographical location as well as national and regional economic factors. This methodology results in loans and sales-type leases being risk rated, with ratings ranging from "1" to "5" with "1" representing the lowest risk of loss and "5" representing the highest risk of loss. The Company estimates its expected loss (“Expected Loss”) on its loans (including unfunded loan commitments), held-to-maturity debt securities and net investment in leases based on relevant information including historical realized loss rates, current market conditions and reasonable and supportable forecasts that affect the collectability of its investments. The estimate of the Company’s Expected Loss requires significant judgment and the Company analyzes its loan portfolio based upon its different categories of financial assets, which includes: (i) loans and held-to-maturity debt securities; (ii) construction loans; and (iii) net investment in leases and financings that resulted from the acquisition of properties that did not qualify as a sale leaseback transaction and, as such, are accounted for as financing receivables (refer to Note 5). For the Company’s loans, held-to-maturity debt securities, construction loans, net investment in leases and financings that resulted from the acquisition of properties that did not qualify as sale leaseback transactions, the Company analyzed its historical realized loss experience to estimate its Expected Loss. The Company adjusted its Expected Loss through the use of third-party market data that provided current and future economic conditions that may impact the performance of the commercial real estate assets securing its investments. The Company considers a loan or sales-type lease to be non-performing and places it on non-accrual status at such time as: (1) interest payments become 90 days delinquent; (2) it has a maturity default; or (3) management determines it is probable that it will be unable to collect all amounts due according to the contractual terms of the loan or sales-type lease. Non-accrual loans or sales-type leases are returned to accrual status when they have become contractually current and management believes all amounts contractually owed will be received. The Company will record a specific allowance on a non-performing loan or sales-type lease if the Company determines that the collateral fair value less costs to sell is less than the carrying value of the collateral-dependent asset. The specific allowance is increased (decreased) through "Provision for (recovery of) loan losses" or "Provision for losses on net investment in leases" in the Company’s consolidated statements of operations and is decreased by charge-offs. During delinquency and the foreclosure process, there are typically numerous points of negotiation with the borrower or tenant as the Company works toward a settlement or other alternative resolution, which can impact the potential for repayment or receipt of collateral. The Company’s policy 55 Table of Contents iStar Inc. Notes to Consolidated Financial Statements is to charge off a loan when it determines, based on a variety of factors, that all commercially reasonable means of recovering the loan balance have been exhausted. This may occur at different times, including when the Company receives cash or other assets in a pre-foreclosure sale or takes control of the underlying collateral in full satisfaction of the loan upon foreclosure or deed-in-lieu, or when the Company has otherwise ceased significant collection efforts. The Company considers circumstances such as the foregoing to be indicators that the final steps in the loan collection process have occurred and that a loan is uncollectible. At this point, a loss is confirmed and the loan and related allowance will be charged off. The Company made the accounting policy election to record accrued interest on its loan portfolio separate from its loans receivable and other lending investments and to exclude accrued interest from its amortized cost basis disclosures (refer to Note 7). As of December 31, 2022 and 2021, accrued interest was $ 0.1 million and $ 1.6 million, respectively, and is recorded in "Accrued interest and operating lease income receivable, net" on the Company’s consolidated balance sheets. The Company places loans on non-accrual status once interest on the loan becomes 90 days delinquent and reverses any accrued interest as a reduction to interest income or recognizes a credit loss expense at such time. As such, the Company elected the practical expedient to not record an allowance against accrued interest receivable. During the years ended December 31, 2022, 2021 and 2020, the Company did not reverse any accrued interest on its loan portfolio. The Company’s two impaired loans are collateral dependent and impairment is measured using the estimated fair value of the collateral, less costs to sell. The Company generally uses the income approach through internally developed valuation models to estimate the fair value of the collateral for such loans. In some cases, the Company obtains external "as is" appraisals for loan collateral, generally when third party participations exist. Valuations are performed or obtained at the time a loan is determined to be impaired or designated non-performing, and they are updated if circumstances indicate that a significant change in value has occurred. In limited cases, appraised values may be discounted when real estate markets rapidly deteriorate. A loan is also considered impaired if its terms are modified in a troubled debt restructuring ("TDR"). A TDR occurs when the Company has granted a concession and the debtor is experiencing financial difficulties. Impairments on TDR loans are generally measured based on the present value of expected future cash flows discounted at the effective interest rate of the original loan. Management evaluates available-for-sale debt securities held in "Loans receivable and other lending investments, net" for impairment if the security’s fair value is less than its amortized cost. If the Company has an impaired security, it will then determine if: (1) the Company has the intent to sell the security; (2) it is more likely than not that it will be required to sell the security before recovery; or (3) it does not expect to recover the entire amortized cost basis of the security. If the Company does not intend to sell the security, it is more likely than not that the entity will not be required to sell the security or it does not expect to recover its amortized cost, the Company will record an allowance for credit losses. The credit loss component of the allowance will be recorded (or reversed, if necessary) as an "Impairment of assets" in the Company’s consolidated statements of operations, and the remainder of the allowance will be recorded in "Accumulated other comprehensive income (loss)" on the Company’s consolidated balance sheets. Loss on debt extinguishments — The Company recognizes the difference between the reacquisition price of debt and the net carrying amount of extinguished debt currently in earnings. Such amounts may include prepayment penalties or the write-off of unamortized debt issuance costs, and are recorded in “Loss on early extinguishment of debt, net” in the Company’s consolidated statements of operations. Derivative instruments and hedging activity — The Company’s use of derivative financial instruments, including derivative financial instruments at some of its equity method investments, is primarily limited to the utilization of interest rate swaps, interest rate caps or other instruments to manage interest rate risk exposure. The Company does not enter into derivatives for trading purposes. The Company recognizes its derivatives as either assets or liabilities on the Company’s consolidated balance sheets at fair value. If certain conditions are met, a derivative may be specifically designated as a hedge of the exposure to changes in the fair value of a recognized asset or liability, a hedge of a forecasted transaction or the variability of cash flows to be received or paid related to a recognized asset or liability. 56 Table of Contents iStar Inc. Notes to Consolidated Financial Statements For derivatives designated and qualifying as cash flow hedges, changes in the fair value of the derivatives, including the Company’s pro rata share of derivatives at equity method investments, are reported as a component of accumulated other comprehensive income (loss) and subsequently reclassified into interest expense or earnings from equity method investments in the same periods during which the hedged transaction affects earnings. Amounts reported in accumulated other comprehensive income related to derivatives will be reclassified to interest expense as interest payments are made on the Company’s debt. For the Company’s derivatives not designated as hedges, the changes in the fair value of the derivatives are reported in "Other expense" in the Company’s consolidated statements of operations. Stock-based compensation — Compensation cost for stock-based awards is measured on the grant date and adjusted over the period of the employees’ services to reflect: (i) actual forfeitures; and (ii) the outcome of awards with performance or service conditions through the requisite service period. Compensation cost for market-based awards is determined using a Monte Carlo model to simulate a range of possible future stock prices for the Company’s common stock, which is reflected in the grant date fair value. All compensation cost for market-based awards in which the service conditions are met is recognized regardless of whether the market-condition is satisfied. Compensation costs are recognized ratably over the applicable vesting/service period and recorded in "General and administrative" in the Company’s consolidated statements of operations. Income taxes — The Company has elected to be qualified and taxed as a REIT under section 856 through 860 of the Internal Revenue Code of 1986, as amended (the "Code"). The Company is subject to federal income taxation at corporate rates on its REIT taxable income; the Company, however, is allowed a deduction for the amount of dividends paid to its shareholders, thereby subjecting the distributed net income of the Company to taxation at the shareholder level only. While the Company must distribute at least 90% of its taxable income to maintain its REIT status, the Company typically distributes all of its taxable income, if any, to eliminate any tax on undistributed taxable income. In addition, the Company is allowed several other deductions in computing its REIT taxable income, including non-cash items such as depreciation expense and certain specific allowance amounts that the Company deems to be uncollectable. These deductions allow the Company to reduce its dividend payout requirement under federal tax laws. The Company intends to operate in a manner consistent with, and its election to be treated as, a REIT for tax purposes. Beginning in 2018, the Tax Cuts and Jobs Act reduced the corporate tax rate to 21% from 35% and net income from foreclosure property, if any, is subject to a 21% tax rate. As of December 31, 2021, the Company had $ 614.6 million of REIT net operating loss ("NOL") carryforwards at the corporate REIT level that can generally be used to offset both ordinary taxable income and capital gain net income in future years. For the year ended December 31, 2022, the Company expects to report REIT taxable income before the deduction for dividends paid and the NOL deduction. The Company will fully utilize its NOL carryforward in its year ended December 31, 2022. The Company’s tax years from 2018 through 2021 remain subject to examination by major tax jurisdictions. The Company recognizes interest expense and penalties related to uncertain tax positions, if any, as "Income tax (expense) benefit" in the Company’s consolidated statements of operations. The Company may participate in certain activities from which it would be otherwise precluded and maintain its qualification as a REIT. These activities are conducted in entities that elect to be treated as taxable subsidiaries under the Code, subject to certain limitations. As such, the Company, through its taxable REIT subsidiaries ("TRS"), is engaged in various real estate related opportunities, primarily related to managing activities related to certain foreclosed assets, as well as managing various investments in equity affiliates. As of December 31, 2022, $ 430.1 million of the Company’s assets were owned by TRS entities. The Company’s TRS entities are not consolidated with the REIT for federal income tax purposes and are taxed as corporations. For financial reporting purposes, current and deferred taxes are provided for on the portion of earnings recognized by the Company with respect to its interest in TRS entities. 57 Table of Contents iStar Inc. Notes to Consolidated Financial Statements The following represents the Company’s TRS income tax benefit (expense) ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ For the Years Ended December 31, ​ 2022 2021 2020 Current tax benefit (expense) (1)(2) ​ $ — ​ $ 82 ​ $ ( 106 ) Total income tax (expense) benefit ​ $ — ​ $ 82 ​ $ ( 106 ) (1) For the years ended December 31, 2022, 2021 and 2020, excludes a REIT tax expense of $ 13.5 million, $ 0.1 million, $ 0.1 million, respectively. (2) Under the Tax Cuts and Jobs Act, the alternative minimum tax credit carryforward is a refundable tax credit over a four year period beginning in 2018 and ending in 2021 upon which the full amount of the credit will be allowed. The CARES Act enacted on March 27, 2020 permits corporate taxpayers to accelerate the full amount of its alternative minimum tax credits. The Company filed a claim for refund and received a $ 3.0 million refund in 2020 for which the benefit had been recognized in 2017. An additional refund of alternative minimum taxes in the amount of $ 0.7 million was received during the year ended December 31, 2021 for which a tax benefit was recorded. During the year ended December 31, 2022, the Company’s TRS entities generated a taxable loss of $ 7.1 million for which the Company did not recognize a net current tax benefit or expense. As of December 31, 2021, the Company’s TRS entities had $ 165.4 million of NOL carryforwards that can generally be used to offset both ordinary taxable income and capital gain net income in future years. The NOL carryforwards will begin to expire in 2036, of which $ 73.6 million will fully expire in 2037, if unused. NOL carryforwards generated in 2018 and thereafter do not expire and are limited to 80% of taxable income when utilized. The amount of NOL carryforwards as of December 31, 2022 will be determined upon finalization of the Company’s 2022 tax return. Total cash paid for taxes for the years ended December 31, 2022, 2021 and 2020 was $ 14.6 million, $ 0.3 million and $ 0.8 million, respectively. Deferred income taxes reflect the net tax effects of temporary differences between the carrying amount of assets and liabilities for financial reporting purposes and the amounts for income tax purposes, as well as operating loss and tax credit carryforwards. The Company applied the corporate tax rate enacted December 22, 2017 under the Tax Cuts and Jobs Act effective for years beginning after 2017 to value its deferred tax assets and liabilities. The Company evaluates whether its deferred tax assets are realizable and recognizes a valuation allowance if, based on the available evidence, both positive and negative, it is more likely than not that some portion or all of its deferred tax assets will not be realized. When evaluating whether its deferred tax assets are realizable, the Company considers, among other matters, estimates of expected future taxable income, nature of current and cumulative losses, existing and projected book/tax differences, tax planning strategies available, and the general and industry specific economic outlook. This analysis is inherently subjective, as it requires the Company to forecast its business and general economic environment in future periods. Based on an assessment of all factors, including historical losses and continued volatility of the activities within the TRS entities, it was determined that full valuation allowances were required on the net deferred tax assets as of December 31, 2022 and 2021, respectively. Changes in estimates of our valuation allowance, if any, are included in “Income tax (expense) benefit” in the consolidated statements of operations. The valuation allowance was reduced to reflect the change in value of our net deferred tax assets that reflects a reduced rate of tax under the Tax Cuts and Jobs Act. Deferred tax assets and liabilities of the Company’s TRS entities were as follows ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ As of December 31, ​ 2022 2021 Deferred tax assets (1) ​ $ 64,900 ​ $ 69,360 Valuation allowance ​ ( 64,900 ) ​ ( 69,360 ) Net deferred tax assets (liabilities) ​ $ — ​ $ — (1) Deferred tax assets as of December 31, 2022 include temporary differences related primarily to asset basis of $ 16.1 million, deferred expenses and other items of $ 5.7 million, NOL carryforwards of $ 40.8 million and other credits of $ 2.3 million. Deferred tax assets as of December 31, 2021 include temporary differences related primarily to asset basis of $ 18.7 million, deferred expenses and other items of $ 8.0 million, NOL carryforwards of $ 40.3 million and other credits of $ 2.4 million. The Company has determined that the change in tax law associated with the Tax Cuts and Jobs Act will not have a material effect on whether its deferred tax assets are realizable. ​ Earnings per share — The Company uses the two-class method in calculating earnings per share ("EPS") when it issues securities other than common stock that contractually entitle the holder to participate in dividends and earnings 58 Table of Contents iStar Inc. Notes to Consolidated Financial Statements of the Company when, and if, the Company declares dividends on its common stock. Basic earnings per share ("Basic EPS") for the Company’s common stock are computed by dividing net income allocable to common shareholders by the weighted average number of shares of common stock outstanding for the period, respectively. Diluted earnings per share ("Diluted EPS") is calculated similarly, however, it reflects the potential dilution that could occur if securities or other contracts to issue common stock were exercised or converted into common stock, where such exercise or conversion would result in a lower earnings per share amount. Net Lease Sale and Discontinued Operations — A discontinued operation represents: (i) a component of the Company or group of components that has been disposed of or is classified as held for sale in a single transaction and represents a strategic shift that has or will have a major effect on the Company’s operations and financial results or (ii) an acquired business that is classified as held for sale on the date of acquisition. ​ In March 2022, the Company, through certain subsidiaries of and entities managed by the Company, closed on a definitive purchase and sale agreement to sell a portfolio of net lease properties owned and managed by such subsidiaries and entities to a third party for an aggregate gross sales price of approximately $ 3.07 billion and recognized a gain of $ 663.7 million in “ Net income from discontinued operations ” in the Company’s consolidated statements of operations. The Company refers to this transaction as the "Net Lease Sale." The Net Lease Sale is consistent with the Company’s stated corporate strategy which is to grow its Ground Lease and Ground Lease adjacent businesses (refer to Note 8) and simplify its portfolio through sales of other assets. ​ The portfolio sold consisted of office, entertainment and industrial properties located in the United States comprising approximately 18.3 million square feet. It included assets wholly-owned by the Company and assets owned by two joint ventures (see Net Lease Venture and Net Lease Venture II below) managed by the Company and in which it owned 51.9 % interests. At the time of closing, the portfolio was encumbered by an aggregate of $ 702.0 million of mortgage indebtedness, including indebtedness from equity method investments, which was repaid with proceeds from the sale. After repayment of the mortgage indebtedness and prepayment penalties, a senior term loan secured by certain of the assets (refer to Note 10), payments to terminate derivative contracts, payments to joint venture partners, and payments of promotes, transaction expenses and amounts due under employee incentive plans, the Company retained net cash proceeds of $ 1.2 billion from the transaction. In addition, as part of the transaction, the buyer sold three of the properties to SAFE for $ 122.0 million and entered into three Ground Leases with SAFE. Two net lease properties were sold to different third parties in the first quarter of 2022 and the Company’s net lease assets associated with its Ground Lease businesses were not included in the sale. After the assumption of debt by the buyer, the Company received net cash proceeds of $ 33.9 million from the sale of the two net lease properties and recognized a gain of $ 23.9 million in “Net income from discontinued operations” in the Company’s consolidated statements of operations. ​ Net Lease Venture —In February 2014, the Company partnered with a sovereign wealth fund to form a venture to acquire and develop net lease assets (the “Net Lease Venture”) and gave a right of first offer to the venture on all new net lease investments. The Company was responsible for sourcing new opportunities and managing the venture and its assets in exchange for a management fee and incentive fee. Several of the Company’s senior executives whose time was substantially devoted to the Net Lease Venture owned a total of 0.6 % equity ownership in the venture via co-investment. These senior executives were also entitled to an amount equal to 50 % of any incentive fee received based on the 47.5 % external partner’s interest. Net Lease Venture was part of the Net Lease Sale. As of December 31, 2022, $ 3.1 million of “Noncontrolling interests” was attributable to the Net Lease Venture and represented proceeds from the Net Lease Sale that were not yet distributed to the Company’s partners in the venture as of December 31, 2022. ​ Net Lease Venture II —In July 2018, the Company entered into a new venture (the “Net Lease Venture II”) with an investment strategy similar to the Net Lease Venture. The Company was responsible for managing the venture in exchange for a management fee and incentive fee. During the year ended December 31, 2022, the Company recorded $ 0.4 million of management fees from Net Lease Venture II in “Net income from discontinued operations” in the Company’s consolidated statements of operations. During the year ended December 31, 2021 and 2020, the Company recorded $ 1.7 million and $ 1.5 million, respectively, of management fees from Net Lease Venture II in “Net income from discontinued operations” in the Company’s consolidated statements of operations. Net Lease Venture II was part of the Net Lease Sale. As of December 31, 2022, $ 2.0 million of “Real estate and other assets available and held for sale and 59 Table of Contents iStar Inc. Notes to Consolidated Financial Statements classified as discontinued operations” was attributable to the Net Lease Venture II and represented proceeds from the Net Lease Sale that were not yet distributed to the Company as of December 31, 2022. ​ The Company’s net lease assets and liabilities associated with the Net Lease Sale and the Company’s other two net lease assets are classified as “Real estate and other assets available and held for sale and classified as discontinued operations” and “Liabilities associated with real estate held for sale and classified as discontinued operations,” respectively, on the Company’s consolidated balance sheets as of December 31, 2021. There are also some residual assets and liabilities from the Net Lease Sale that are classified as “Real estate and other assets available and held for sale and classified as discontinued operations” and “Liabilities associated with real estate held for sale and classified as discontinued operations,” respectively, on the Company’s consolidated balance sheets as of December 31, 2022. For the years ended December 31, 2022, 2021 and 2020, the operations of such assets are classified in “Net income from discontinued operations” in the Company’s consolidated statements of operations. ​ The following table presents the Company’s consolidated assets and liabilities recorded in “Real estate and other assets available and held for sale and classified as discontinued operations” and “Liabilities associated with real estate held for sale and classified as discontinued operations,” respectively, on the Company’s consolidated balance sheets as of December 31, 2022 and 2021 ($ in thousands). ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ As of ​ ​ ​ December 31, ​ ​ ​ 2022 2021 ​ ASSETS ​ ​ ​ ​ Real estate ​ ​ ​ ​ Real estate, at cost ​ $ — ​ $ 1,537,655 ​ Less: accumulated depreciation ​ — ​ ( 271,183 ) ​ Total real estate, net ​ — ​ 1,266,472 ​ Net investment in leases ​ — ​ 486,389 ​ Loans receivable held for sale ​ ​ — ​ ​ 48,675 ​ Other investments ​ 1,963 ​ 103,229 ​ Finance lease right of use assets ​ ​ — ​ ​ 150,099 ​ Accrued interest and operating lease income receivable, net ​ 492 ​ 2,997 ​ Deferred operating lease income receivable, net ​ — ​ 63,156 ​ Deferred expenses and other assets, net ​ 484 ​ 178,694 ​ Total real estate and other assets available and held for sale and classified as discontinued operations ​ $ 2,939 ​ $ 2,299,711 ​ ​ ​ ​ ​ LIABILITIES ​ ​ ​ Accounts payable, accrued expenses and other liabilities ​ $ 333 ​ $ 92,865 ​ Finance lease liabilities ​ ​ — ​ ​ 161,258 ​ Debt obligations, net ​ — ​ 714,296 ​ Total liabilities associated with real estate held for sale and classified as discontinued operations ​ $ 333 ​ $ 968,419 ​ ​ 60 Table of Contents iStar Inc. Notes to Consolidated Financial Statements The transaction described above involving the Company's net lease business qualified for discontinued operations and the following table summarizes net income from discontinued operations for the years ended December 31, 2022, 2021 and 2020 ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ For the Years Ended December 31, ​ ​ 2022 2021 2020 Revenues: ​ ​ ​ ​ Operating lease income ​ $ 35,596 ​ $ 164,811 ​ $ 164,446 Interest income ​ 885 ​ 3,717 ​ 3,440 Interest income from sales-type leases ​ 8,803 ​ 35,826 ​ 33,552 Other income ​ 4,292 ​ 5,178 ​ 5,412 Total revenues ​ 49,576 ​ 209,532 ​ 206,850 Costs and expenses: ​ ​ ​ Interest expense (1) ​ 7,484 ​ 43,232 ​ 42,746 Real estate expense ​ 5,072 ​ 27,366 ​ 26,410 Depreciation and amortization (1) ​ — ​ 52,221 ​ 50,765 (Recovery of) provision for loan losses ​ ​ — ​ ​ ( 1,150 ) ​ ​ 186 (Recovery of) provision for losses on net investment in leases ​ — ​ ( 10,871 ) ​ 1,760 Impairment of assets ​ 1,492 ​ 2,286 ​ 2,036 Other expense (2) ​ ( 5,669 ) ​ 16,476 ​ — Total costs and expenses ​ 8,379 ​ 129,560 ​ 123,903 Income from sales of real estate ​ 683,738 ​ 8,476 ​ — Income from discontinued operations before earnings from equity method investments and other items ​ 724,935 ​ 88,448 ​ 82,947 Loss on early extinguishment of debt, net ​ ( 41,408 ) ​ — ​ — Earnings from equity method investments ​ 127,129 ​ 8,123 ​ 2,654 Selling profit from sales-type leases ​ — ​ 25,034 ​ — Net income from discontinued operations before income taxes ​ 810,656 ​ 121,605 ​ 85,601 Income tax expense ​ ( 12,968 ) ​ ( 153 ) ​ ( 146 ) Net income from discontinued operations ​ ​ 797,688 ​ ​ 121,452 ​ ​ 85,455 Net (income) from discontinued operations attributable to noncontrolling interests ​ ( 179,089 ) ​ ( 5,620 ) ​ ( 11,251 ) Net income from discontinued operations attributable to iStar Inc. ​ $ 618,599 ​ $ 115,832 ​ $ 74,204 (1) For the years ended December 31, 2022, 2021 and 2020, the Company recorded $ 1.3 million, $ 8.4 million and $ 8.2 million, respectively, of “Interest expense” in its consolidated statements of operations from its Ground Leases with SAFE. During the years ended December 31, 2021 and 2020, the Company recognized $ 1.5 million and $ 1.5 million, respectively, of “Depreciation and amortization” in its consolidated statements of operations from its Ground Leases with SAFE. 61 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Represents the reversal of other expenses recognized in connection with the settlement of interest rate hedges during the year ended December 31, 2022. 62 Table of Contents iStar Inc. Notes to Consolidated Financial Statements (2) The following table presents cash flows provided by operating activities and cash flows used in investing activities from discontinued operations for the years ended December 31, 2022, 2021 and 2020 ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ For the Years Ended December 31, ​ ​ 2022 2021 2020 Cash flows provided by operating activities ​ $ 115,140 ​ $ 85,249 ​ $ 112,783 Cash flows provided by (used in) investing activities ​ 2,668,531 ​ 2,030 ​ ( 51,998 ) ​ New accounting pronouncements — In March 2020, the Financial Accounting Standards Board issued ASU 2020-04, Reference Rate Reform (“ASU 2020-04”). ASU 2020-04 contains practical expedients for reference rate reform related activities that impact debt, leases, derivatives and other contracts. The guidance in ASU 2020-04 is optional and may be elected over time as reference rate reform activities occur. In March 2020, the Company elected to apply the hedge accounting expedients related to probability and the assessments of effectiveness for future LIBOR-indexed cash flows to assume that the index upon which future hedged transactions will be based matches the index on the corresponding derivatives. Application of these expedients preserves the presentation of derivatives consistent with past presentation. The Company continues to evaluate the impact of the guidance and may apply other elections as applicable as additional changes in the market occur. In March 2022, the Financial Accounting Standards Board issued ASU 2022-02, Financial Instruments—Credit Losses: Troubled Debt Restructurings and Vintage Disclosures (“ASU 2022-02”). ASU 2022-02 was issued to eliminate troubled debt restructuring recognition and measurement guidance and required disclosure of gross write-offs by vintage for public business entities. ASU 2022-02 is effective for annual reporting periods beginning after December 15, 2022. Early adoption is permitted. Management is currently evaluating the impact of ASU 2022-02 and does not expect ASU 2022-02 to have a material impact on the Company’s consolidated financial statements. Note 4—Real Estate The Company’s real estate assets were comprised of the following ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ December 31, December 31, ​ ​ 2022 ​ 2021 Land, at cost ​ $ 5,570 ​ $ 6,831 Buildings and improvements, at cost ​ 89,023 ​ 106,679 Less: accumulated depreciation ​ ( 18,096 ) ​ ( 21,360 ) Real estate, net ​ 76,497 ​ 92,150 Real estate available and held for sale (1) ​ 3,977 ​ 301 Total real estate ​ $ 80,474 ​ $ 92,451 (1) As of December 31, 2022 and 2021, the Company had $ 4.0 million and $ 0.3 million, respectively, of residential homes/condominiums available for sale in its operating properties portfolio. Dispositions— Refer to Note 3 - Net Lease Sale and Discontinued Operations. ​ During the year ended December 31, 2022, the Company sold an operating property with a carrying value of $ 14.4 million and recognized gains of $ 25.2 million in “Income from sales of real estate” in the Company’s consolidated statements of operations. During the year ended December 31, 2021, the Company sold a commercial operating property with a carrying value of $ 96.8 million and recognized gains of $ 25.6 million and sold residential operating properties and recognized gains of $ 0.7 million in “Income from sales of real estate” in the Company’s consolidated statements of operations. ​ Real Estate Available and Held for Sale— During the year ended December 31, 2021, the Company transferred an operating property with a carrying value of $ 96.8 million to held for sale prior to its disposition in 2021. ​ Impairments— During the years ended December 31, 2022, 2021 and 2020, the Company recorded aggregate impairments on real estate assets totaling $ 2.4 million, $ 0.6 million and $ 3.1 million, respectively. During the year ended 63 Table of Contents iStar Inc. Notes to Consolidated Financial Statements December 31, 2022, the Company recognized an aggregate impairment of $ 2.4 million on residential homes held for sale and on an operating property based on the expected cash flows to be received. During the year ended December 31, 2021, the Company recorded an impairment of $ 0.6 million on an operating property. During the year ended December 31, 2020, the Company recorded an impairment of $ 3.1 million on a real estate asset held for sale. Tenant Reimbursements— The Company receives reimbursements from tenants for certain facility operating expenses including common area costs, insurance, utilities and real estate taxes and are included in “Operating lease income” in the Company’s consolidated statements of operations. Tenant expense reimbursements were $ 3.1 million, $ 2.9 million and $ 3.6 million for the years ended December 31, 2022, 2021 and 2020, respectively. Allowance for Doubtful Accounts— As of both December 31, 2022 and 2021, the allowance for doubtful accounts related to real estate tenant receivables was $ 0.1 million. These amounts are included in “Accrued interest and operating lease income receivable, net” on the Company’s consolidated balance sheets. Future Minimum Operating Lease Payments— Future minimum operating lease payments to be collected under non-cancelable operating leases, excluding lease payments for assets that are classified as discontinued operations and customer reimbursements of expenses, in effect as of December 31, 2022, are as follows by year ($ in thousands): (1) ​ ​ ​ ​ ​ ​ Operating Year ​ Properties 2023 ​ $ 4,183 2024 ​ 4,129 2025 ​ 4,145 2026 ​ 4,203 2027 ​ 1,570 Thereafter ​ ​ 1,117 Total ​ $ 19,347 (1) Refer to Note 3 - Net Lease Sale and Discontinued Operations . . ​ ​ ​ Note 5—Net Investment in Leases In June 2021, the Company acquired two parcels of land for $ 42.0 million each and simultaneously entered into two Ground Leases with the respective tenants. Each Ground Lease also provides for a leasehold improvement allowance up to a maximum of $ 83.0 million. The Company also concurrently entered into an agreement pursuant to which SAFE would acquire the Ground Leases from the Company. If certain construction conditions are not met within a specified time period, SAFE will have no obligation to acquire the Ground Leases or fund the leasehold improvement allowances. The Company classified one of the Ground Leases as a sales-type lease and it was recorded in “Net investment in leases” on the Company’s consolidated balance sheet at the time of acquisition. One Ground Lease was entered into with the seller of the land and did not qualify for sale leaseback accounting, and as such, was accounted for as a financing transaction and $ 42.0 million was recorded in “Loans receivable held for sale” on the Company’s consolidated balance sheet at the time of acquisition. In January 2022, the Company sold the Ground Leases to an investment fund in which the Company owns a 53 % noncontrolling interest (refer to Note 8 – Ground Lease Plus Fund). There can be no assurance that the conditions to closing will be satisfied and that SAFE will acquire the properties and Ground Leases from the Ground Lease Plus Fund. In January 2022, the Company entered into a commitment to acquire land for $ 36.0 million and simultaneously structured and entered into a Ground Lease as part of the Ground Lease tenant’s recapitalization of an existing multifamily property. The Company funded $ 34.6 million of its commitment and then, pursuant to an agreement with SAFE (refer to Note 8) and upon certain construction related conditions being met, sold the Ground Lease to SAFE in July 2022 for $ 36.0 million and recognized a gain of $ 1.0 million in “Income from sales of real estate” in its consolidated statements of operations. 64 Table of Contents iStar Inc. Notes to Consolidated Financial Statements The Company’s net investment in leases were comprised of the following as of December 31, 2022 and 2021 ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ December 31, 2022 December 31, 2021 Total undiscounted cash flows ​ $ — ​ $ 524,712 Unguaranteed estimated residual value ​ — ​ 42,000 Present value discount ​ — ​ ( 523,497 ) Net investment in leases (1) ​ $ — ​ $ 43,215 (1) As of December 31, 2021, the Company’s net investment in lease was current in its payment status and performing in accordance with the terms of the lease. As of December 31, 2021, the risk rating on the Company’s net investment in leases was 1.0 . Allowance for Losses on Net Investment in Leases —Changes in the Company’s allowance for losses on net investment in leases for the years ended December 31, 2022 and 2021 were as follows ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Year Ended ​ ​ December 31, 2022 December 31, 2021 ​ Allowance for losses on net investment in leases at beginning of period (1) $ — ​ $ 10,871 Provision for (recovery of) losses on net investment in leases included in discontinued operations (1) ​ ​ — ​ ​ ( 10,871 ) ​ Allowance for losses on net investment in leases at end of period (1) ​ $ — ​ $ — ​ (1) Refer to Note 3 - Net Lease Sale and Discontinued Operations. During the year ended December 31, 2021, the Company recorded a recovery of losses on net investment in leases of $ 10.9 million. The recovery of losses on net investment in leases for the year ended December 31, 2021 resulted primarily from the cash flows the Company received upon disposition of the Company’s net investment in leases included in “Real estate and other assets available and held for sale and classified as discontinued operations” and “Net investment in leases” on the Company’s consolidated balance sheets. ​ Note 6—Land and Development The Company’s land and development assets were comprised of the following ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ As of ​ ​ ​ December 31, ​ December 31, ​ ​ 2022 2021 ​ Land and land development, at cost ​ $ 243,727 ​ $ 297,621 ​ Less: accumulated depreciation ​ ( 11,713 ) ​ ( 10,811 ) ​ Total land and development, net ​ $ 232,014 ​ $ 286,810 ​ ​ Dispositions— During the years ended December 31, 2022, 2021 and 2020, the Company sold land parcels and residential lots and units and recognized land development revenue of $ 61.8 million, $ 189.1 million and $ 164.7 million, respectively. During the years ended December 31, 2022, 2021 and 2020, the Company recognized land development cost of sales of $ 63.4 million, $ 172.0 million and $ 177.7 million, respectively, from its land and development portfolio. Impairments— During the year ended December 31, 2022, the Company recorded an impairment of $ 12.7 million on a land and development asset due to a change in business strategy. During the year ended December 31, 2020, the Company recorded an aggregate impairment of $ 2.7 million on two land and development assets. 65 Table of Contents iStar Inc. Notes to Consolidated Financial Statements . Note 7—Loans Receivable and Other Lending Investments, net The following is a summary of the Company’s loans receivable and other lending investments by class ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ As of ​ ​ December 31, 2022 December 31, 2021 ​ Construction loans ​ ​ ​ ​ ​ ​ ​ Senior mortgages ​ $ 36,249 ​ $ 184,643 ​ Corporate/Partnership loans ​ — ​ 618 ​ Subtotal - gross carrying value of construction loans (1) ​ 36,249 ​ 185,261 ​ Loans ​ ​ ​ Senior mortgages ​ — ​ 14,965 ​ Subordinate mortgages ​ 13,331 ​ 12,457 ​ Subtotal - gross carrying value of loans ​ 13,331 ​ 27,422 ​ Other lending investments ​ ​ ​ Held-to-maturity debt securities ​ — ​ 96,838 ​ Available-for-sale debt securities ​ — ​ 28,092 ​ Subtotal - other lending investments ​ — ​ 124,930 ​ Total gross carrying value of loans receivable and other lending investments ​ 49,580 ​ 337,613 ​ Allowance for loan losses ​ ( 925 ) ​ ( 4,769 ) ​ Total loans receivable and other lending investments, net ​ $ 48,655 ​ $ 332,844 ​ (1) As of December 31, 2022, 100 % of gross carrying value of construction loans had completed construction. 66 Table of Contents iStar Inc. Notes to Consolidated Financial Statements ​ Allowance for Loan Losses — Changes in the Company’s allowance for loan losses were as follows for the years ended December 31, 2022, 2021 and 2020 ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ General Allowance ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Held to ​ ​ ​ ​ ​ ​ Construction ​ ​ ​ ​ Maturity Debt ​ Specific ​ ​ ​ Year Ended December 31, 2022 ​ Loans ​ Loans ​ Securities ​ Allowance ​ Total Allowance for loan losses at beginning of period ​ $ 1,213 ​ $ 676 ​ $ 2,304 ​ $ 576 ​ $ 4,769 Provision for (recovery of) loan losses (1) ​ ​ ( 725 ) ​ ( 239 ) ​ — ​ 46,034 ​ ​ 45,070 Transfers ​ ​ ( 396 ) ​ ​ — ​ ​ ( 2,304 ) ​ ​ 2,700 ​ ​ — Charge-offs (1) ​ ​ — ​ ​ — ​ ​ — ​ ​ ( 48,914 ) ​ ​ ( 48,914 ) Allowance for loan losses at end of period ​ $ 92 ​ $ 437 ​ $ — ​ $ 396 ​ $ 925 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Year Ended December 31, 2021 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Allowance for loan losses at beginning of period ​ $ 6,541 ​ $ 1,643 ​ $ 3,093 ​ $ 743 ​ $ 12,020 Recovery of loan losses (1) ​ ( 5,328 ) ​ ( 967 ) ​ ( 789 ) ​ ( 167 ) ​ ( 7,251 ) Allowance for loan losses at end of period ​ $ 1,213 ​ $ 676 ​ $ 2,304 ​ $ 576 ​ $ 4,769 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Year Ended December 31, 2020 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Allowance for loan losses at beginning of period ​ $ 6,668 ​ $ 265 ​ $ — ​ $ 21,701 ​ $ 28,634 Adoption of new accounting standard (2) ​ ( 353 ) ​ 98 ​ 20 ​ — ​ ( 235 ) Provision for loan losses (1) ​ 226 ​ 1,280 ​ 3,073 ​ 4,931 ​ 9,510 Charge-offs (3) ​ — ​ — ​ — ​ ( 25,889 ) ​ ( 25,889 ) Allowance for loan losses at end of period ​ $ 6,541 ​ $ 1,643 ​ $ 3,093 ​ $ 743 ​ $ 12,020 (1) During the year ended December 31, 2022, the Company recorded a provision for (recovery of) loan losses of $ 45.0 million in its consolidated statements of operations. The provision in 2022 was due primarily to a $ 22.2 million specific provision on the Company’s held-to-maturity debt security, which was recorded at its repayment proceeds and a provision of $ 23.8 million on one loan prior to it being transferred to held for sale. During the year ended December 31, 2021, the Company recorded a recovery of loan losses of $ 8.1 million in its consolidated statement of operations resulting from the repayment of loans during the period and an improving macroeconomic impact of the COVID-19 pandemic on commercial real estate markets, of which $ 1.0 million related to a provision for credit losses for unfunded loan commitments and is recorded as a reduction to "Accounts payable, accrued expenses and other liabilities". During the year ended December 31, 2020, the Company recorded a provision for loan losses of $ 8.9 million in its consolidated statement of operations resulting from the macroeconomic impact of the COVID-19 pandemic on commercial real estate markets, of which $ 1.5 million related to a recovery of credit losses for unfunded loan commitments and is recorded as a reduction to "Accounts payable, accrued expenses and other liabilities" and $ 0.9 million related to a provision on a non-performing loan that was recorded as a reduction to "Accrued interest and operating lease income receivable, net." (2) On January 1, 2020, the Company recorded an increase to its allowance for loan losses of $ 2.3 million upon the adoption of ASU 2016-13, of which $ 2.5 million related to expected credit losses for unfunded loan commitments and was recorded in "Accounts payable, accrued expenses and other liabilities." (3) During the year ended December 31, 2020, the Company charged-off $ 25.9 million from the specific allowance due to the sale of a non-performing loan. 67 Table of Contents iStar Inc. Notes to Consolidated Financial Statements The Company’s investment in loans and other lending investments and the associated allowance for loan losses were as follows ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Individually Collectively ​ ​ ​ ​ Evaluated for ​ Evaluated for ​ ​ ​ ​ ​ Impairment (1) ​ Impairment ​ Total As of December 31, 2022 ​ ​ ​ Construction loans (2) ​ $ 29,493 ​ $ 6,756 ​ $ 36,249 Loans (2) ​ — ​ 13,331 ​ 13,331 Less: Allowance for loan losses ​ ( 396 ) ​ ( 529 ) ​ ( 925 ) Total ​ $ 29,097 ​ $ 19,558 ​ $ 48,655 As of December 31, 2021 ​ ​ ​ Construction loans (2) ​ $ 59,640 ​ $ 125,621 ​ $ 185,261 Loans (2) ​ — ​ 27,422 ​ 27,422 Held-to-maturity debt securities ​ — ​ 96,838 ​ 96,838 Available-for-sale debt securities (3) ​ — ​ 28,092 ​ 28,092 Less: Allowance for loan losses ​ ( 576 ) ​ ( 4,193 ) ​ ( 4,769 ) Total ​ $ 59,064 ​ $ 273,780 ​ $ 332,844 (1) The carrying value of these loans includes amortized fees of $ 0.1 million and $ 0.8 million as of December 31, 2022 and 2021, respectively. The Company’s loans individually evaluated for impairment represent loans on non-accrual status and the unamortized amounts associated with these loans are not currently being amortized into income. (2) The carrying value of these loans includes an unamortized net discount of $ 0.2 million as of December 31, 2021. (3) Available-for-sale debt securities were evaluated for impairment under ASC 326-30 – Financial Instruments-Credit Losses. Credit Characteristics —As part of the Company’s process for monitoring the credit quality of its loans, it performs a quarterly loan portfolio assessment and assigns risk ratings to each of its performing loans. Risk ratings, which range from 1 (lower risk) to 5 (higher risk), are based on judgments which are inherently uncertain and there can be no assurance that actual performance will be similar to current expectation. ​ 68 Table of Contents iStar Inc. Notes to Consolidated Financial Statements The Company’s amortized cost basis in performing senior mortgages, corporate/partnership loans and subordinate mortgages, presented by year of origination and by credit quality, as indicated by risk rating, was as follows as of December 31, 2022 ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Year of Origination ​ ​ 2022 2021 2020 2019 2018 Prior to 2018 Total Senior mortgages ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Risk rating ​ ​ ​ ​ ​ ​ ​ ​ ​ 1.0 ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — 1.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 2.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 2.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 3.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 3.5 ​ — ​ — ​ — ​ — ​ 6,756 ​ — ​ 6,756 4.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 4.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 5.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — Subtotal (1) ​ $ — ​ $ — ​ $ — ​ $ — ​ $ 6,756 ​ $ — ​ $ 6,756 Corporate/partnership loans ​ ​ ​ ​ ​ ​ ​ Risk rating ​ ​ ​ ​ ​ ​ ​ 1.0 ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — 1.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 2.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 2.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 3.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 3.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 4.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 4.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 5.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — Subtotal ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — Subordinate mortgages ​ ​ ​ ​ ​ ​ ​ Risk rating ​ ​ ​ ​ ​ ​ ​ 1.0 ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — 1.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 2.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 2.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 3.0 ​ — ​ — ​ — ​ — ​ — ​ 13,331 ​ 13,331 3.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 4.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 4.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 5.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — Subtotal ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ 13,331 ​ $ 13,331 Total ​ $ — ​ $ — ​ $ — ​ $ — ​ $ 6,756 ​ $ 13,331 ​ $ 20,087 (1) As of December 31, 2022, excludes $ 29.5 million for one loan on non-accrual status. ​ 69 Table of Contents iStar Inc. Notes to Consolidated Financial Statements The Company’s amortized cost basis in performing senior mortgages, corporate/partnership loans and subordinate mortgages, presented by year of origination and by credit quality, as indicated by risk rating, was as follows as of December 31, 2021 ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Year of Origination ​ ​ 2021 2020 2019 2018 2017 Prior to 2017 Total Senior mortgages ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Risk rating ​ ​ ​ ​ ​ ​ ​ ​ ​ 1.0 ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — 1.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 2.0 ​ — ​ — ​ — ​ 11,909 ​ — ​ — ​ 11,909 2.5 ​ — ​ — ​ — ​ 52,161 ​ — ​ — ​ 52,161 3.0 ​ — ​ — ​ — ​ 58,522 ​ — ​ 3,056 ​ 61,578 3.5 ​ — ​ — ​ — ​ 14,320 ​ — ​ — ​ 14,320 4.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 4.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 5.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — Subtotal (1) ​ $ — ​ $ — ​ $ — ​ $ 136,912 ​ $ — ​ $ 3,056 ​ $ 139,968 Corporate/partnership loans ​ ​ ​ ​ ​ ​ ​ Risk rating ​ ​ ​ ​ ​ ​ ​ 1.0 ​ $ — ​ $ — ​ $ — ​ $ 618 ​ $ — ​ $ — ​ $ 618 1.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 2.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 2.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 3.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 3.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 4.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 4.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 5.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — Subtotal ​ $ — ​ $ — ​ $ — ​ $ 618 ​ $ — ​ $ — ​ $ 618 Subordinate mortgages ​ ​ ​ ​ ​ ​ ​ Risk rating ​ ​ ​ ​ ​ ​ ​ 1.0 ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — 1.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 2.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 2.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 3.0 ​ — ​ — ​ — ​ — ​ — ​ 12,457 ​ 12,457 3.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 4.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 4.5 ​ — ​ — ​ — ​ — ​ — ​ — ​ — 5.0 ​ — ​ — ​ — ​ — ​ — ​ — ​ — Subtotal ​ $ — ​ $ — ​ $ — ​ $ — ​ $ — ​ $ 12,457 ​ $ 12,457 Total ​ $ — ​ $ — ​ $ — ​ $ 137,530 ​ $ — ​ $ 15,513 ​ $ 153,043 (1) As of December 31, 2021, excludes $ 59.6 million for one loan on non-accrual status. ​ 70 Table of Contents iStar Inc. Notes to Consolidated Financial Statements The Company’s amortized cost basis in loans, aged by payment status and presented by class, was as follows ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Less Than Greater ​ ​ ​ ​ ​ ​ ​ ​ ​ or Equal ​ Than ​ Total ​ ​ ​ ​ ​ Current ​ to 90 Days ​ 90 Days ​ Past Due ​ Total As of December 31, 2022 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Senior mortgages ​ $ 6,756 ​ $ 29,493 ​ $ — ​ ​ 29,493 ​ $ 36,249 Subordinate mortgages ​ 13,331 ​ — ​ — ​ — ​ 13,331 Total ​ $ 20,087 ​ $ 29,493 ​ $ — ​ $ 29,493 ​ $ 49,580 As of December 31, 2021 ​ ​ ​ ​ ​ Senior mortgages (1) ​ $ 139,968 ​ $ — ​ $ 59,640 ​ ​ 59,640 ​ $ 199,608 Corporate/Partnership loans ​ 618 ​ — ​ — ​ — ​ 618 Subordinate mortgages ​ 12,457 ​ — ​ — ​ — ​ 12,457 Total ​ $ 153,043 ​ $ — ​ $ 59,640 ​ $ 59,640 ​ $ 212,683 (1) Loan past due was transferred to held for sale as of December 31, 2022. Impaired Loans —In the fourth quarter 2022, the Company classified a loan with a carrying value of $ 29.1 million as non-performing upon maturity default. In the fourth quarter 2020, the Company sold a non-performing loan with a carrying value of $ 15.2 million and received proceeds of $ 11.0 million. In addition, the Company recorded a $ 4.2 million loan loss provision and simultaneously charged-off of the remaining unpaid balance. The Company’s impaired loans, presented by class, were as follows ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ As of December 31, 2022 As of December 31, 2021 ​ ​ ​ Unpaid ​ ​ ​ ​ Unpaid ​ ​ ​ ​ Amortized ​ Principal ​ Related ​ Amortized ​ Principal ​ Related ​ ​ Cost ​ Balance ​ Allowance ​ Cost ​ Balance ​ Allowance With an allowance recorded: ​ ​ ​ ​ ​ ​ ​ ​ Senior mortgages (1) ​ $ 29,493 ​ $ 29,358 ​ $ ( 396 ) ​ $ 59,640 ​ $ 58,888 ​ $ ( 576 ) Total ​ $ 29,493 ​ $ 29,358 ​ $ ( 396 ) ​ $ 59,640 ​ $ 58,888 ​ $ ( 576 ) (1) The Company has one non-accrual loan as of December 31, 2022 and 2021 that is considered impaired and included in the table above. The Company did no t record any interest income on impaired loans for the years ended December 31, 2022, 2021 and 2020. The Company’s average recorded investment in impaired loans and interest income recognized, presented by class, was as follows ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Years Ended December 31, ​ ​ 2022 ​ 2021 ​ 2020 ​ Average Interest Average Interest Average Interest ​ ​ Recorded ​ Income ​ Recorded ​ Income ​ Recorded ​ Income ​ ​ Investment ​ Recognized ​ Investment ​ Recognized ​ Investment ​ Recognized With an allowance recorded: ​ ​ ​ ​ ​ ​ Senior mortgages ​ $ 45,032 ​ $ — ​ $ 57,853 ​ $ — ​ $ 50,205 ​ $ 2,145 Total ​ $ 45,032 ​ $ — ​ $ 57,853 ​ $ — ​ $ 50,205 ​ $ 2,145 ​ Loans receivable held for sale —In December 2022, the Company began marketing a non-performing loan for sale and classified the loan in “Loans receivable held for sale” on the Company’s consolidated balance sheet. Prior to its transfer to loans receivable held for sale, the Company recorded a provision for loan losses of $ 23.8 million on the loan based on the Company’s intent to sell the loan based on a bid received from a third-party. The loan is recorded on the Company’s consolidated balance sheet at the estimated sales price of $ 37.7 million. 71 Table of Contents iStar Inc. Notes to Consolidated Financial Statements In March 2021, the Company acquired land and simultaneously structured and entered into with the seller a Ground Lease on which a multi-family project will be constructed. The Company funded $ 16.1 million at closing and the Ground Lease documents provided for future funding obligations to the Ground Lease tenant of approximately $ 11.9 million of deferred purchase price and $ 52.0 million of leasehold improvement allowance upon achievement of certain milestones. At closing, the Company entered into an agreement with SAFE pursuant to which, subject to certain conditions being met, SAFE would acquire the ground lessor entity from the Company. The Company determined that the transaction did not qualify as a sale leaseback transaction and recorded the Ground Lease in “Loans receivable held for sale” on the Company’s consolidated balance sheet. Subsequent to closing, the Company funded approximately $ 6.0 million of the deferred purchase price to the Ground Lease tenant. The Company sold the ground lessor entity (and SAFE assumed all future funding obligations to the Ground Lease tenant) to SAFE in September 2021 for $ 22.1 million and recorded no gain or loss on the sale. In June 2021, the Company acquired a parcel of land for $ 42.0 million and simultaneously entered into a Ground Lease (refer to Note 5). The Company also concurrently entered into an agreement pursuant to which SAFE would acquire the Ground Lease from the Company. The Ground Lease was entered into with the seller of the land and did not qualify for sale leaseback accounting, and as such, was accounted for as a financing transaction and $ 42.0 million was recorded in “Loans receivable held for sale” on the Company’s consolidated balance sheet at the time of acquisition. In January 2022, the Company sold its loan receivable held for sale to the Ground Lease Plus Fund (refer to Note 8). Other lending investments —Other lending investments includes the following securities ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Net ​ ​ Net ​ ​ ​ ​ ​ Amortized ​ Unrealized ​ Estimated ​ Carrying ​ ​ Face Value ​ Cost Basis ​ Gain ​ Fair Value ​ Value As of December 31, 2021 ​ ​ ​ ​ ​ Available-for-Sale Securities (1) ​ ​ ​ ​ ​ Municipal debt securities ​ $ 23,855 ​ $ 23,855 ​ $ 4,237 ​ $ 28,092 ​ $ 28,092 Held-to-Maturity Securities (2) ​ ​ ​ ​ ​ ​ ​ ​ ​ Debt securities ​ 100,000 ​ 96,838 ​ — ​ 96,838 ​ 96,838 Total ​ $ 123,855 ​ $ 120,693 ​ $ 4,237 ​ $ 124,930 ​ $ 124,930 (1) During the year ended December 31, 2022, the Company sold its available-for-sale securities and recognized a gain of $ 2.9 million, which is recorded in “Other income” in the Company’s consolidated statements of operations . (2) During the year ended December 31, 2022, the Company received $ 75.0 million of repayments and recorded a $ 22.2 million provision in ‘Provision for (recovery of) loan losses” in its consolidated statements of operations on its debt security. ​ ​ ​ ​ ​ ​ 72 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Note 8—Other Investments The Company’s other investments and its proportionate share of earnings (losses) from equity method investments were as follows ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Carrying Value ​ Equity in Earnings (Losses) ​ ​ As of December 31, For the Years Ended December 31, ​ ​ 2022 2021 ​ 2022 2021 2020 Real estate equity investments ​ ​ ​ ​ ​ ​ ​ Safehold Inc. ("SAFE") (1) ​ $ 1,237,086 ​ $ 1,168,532 ​ $ 38,885 ​ $ 108,393 ​ $ 53,476 Ground Lease Plus Fund ​ 65,791 ​ 17,630 ​ 2,807 ​ 6 ​ — Other real estate equity investments (2) ​ 32,405 ​ 44,349 ​ 19,625 ​ 36,600 ​ ( 12,929 ) Subtotal ​ 1,335,282 ​ 1,230,511 ​ 61,317 ​ 144,999 ​ 40,547 Other strategic investments (3) ​ 25,400 ​ 66,770 ​ ( 2,637 ) ​ 9,345 ​ ( 1,075 ) Total ​ $ 1,360,682 ​ $ 1,297,281 ​ $ 58,680 ​ $ 154,344 ​ $ 39,472 (1) As of December 31, 2022, the Company owned 33.9 million shares of SAFE common stock which, based on the closing price of $ 28.62 on December 31, 2022, had a market value of $ 1.0 billion. P ursuant to ASC 323-10-40-1, an equity method investor shall account for a share issuance by an investee as if the investor had sold a proportionate share of its investment. Any gain or loss to the investor resulting from an investee’s share issuance shall be recognized in earnings. For the years ended December 31, 2022, 2021 and 2020, equity in earnings includes $ 0.9 million, $ 60.7 million and $ 14.4 million, respectively, of dilution gains resulting from SAFE equity offerings. During the year ended December 31, 2022, the Company distributed shares of SAFE common stock to its shareholders in the form of a dividend and realized a loss of $ 49.3 million on the distribution in equity in earnings from equity method investments. (2) During the year ended December 31, 2022, one of the Company’s real estate equity investments closed on the sale of a multifamily property. The Company received a distribution of $ 15.9 million from the sale and recognized a gain of $ 11.5 million in “Earnings from equity method investments” in the Company’s consolidated statements of operations. (3) During the years ended December 31, 2021 and 2020, the Company identified observable price changes in an equity security held by the Company as evidenced by orderly private issuances of similar securities by the same issuer. In accordance with ASC 321, the Company remeasured its equity investment at fair value and recognized aggregate mark-to-market gains during the years ended December 31, 2021 and 2020 of $ 18.9 million and $ 23.9 million, respectively, in “Other income” in the Company’s consolidated statements of operations. The Company’s equity security was redeemed at its carrying value in the fourth quarter of 2021. Safehold Inc. —Refer to Note 1 – Merger with Safehold Inc. SAFE is a publicly-traded company formed by the Company primarily to acquire, own, manage, finance and capitalize ground leases. Ground leases generally represent ownership of the land underlying commercial real estate projects that is net leased by the fee owner of the land to the owners/operators of the real estate projects built thereon (“Ground Leases”). In January 2019, the Company purchased 12.5 million newly designated limited partnership units (the “Investor Units”) in SAFE’s operating partnership (“SAFE OP”), at a purchase price of $ 20.00 per unit, for a total purchase price of $ 250.0 million. In May 2019, after the approval of SAFE’s shareholders, the Investor Units were exchanged for shares of SAFE’s common stock on a one -for-one basis. Following the exchange, the Investor Units were retired. In connection with the Company’s purchase of the Investor Units, it entered into a Stockholder’s Agreement with SAFE in January 2019. The Stockholder’s Agreement: ● limits the Company’s discretionary voting power to 41.9 % of the outstanding voting power of SAFE’s common stock until its aggregate ownership of SAFE common stock is less than 41.9 % ; and ● provides the Company certain preemptive rights. A wholly-owned subsidiary of the Company is the external manager of SAFE and is entitled to a management fee. In addition, the Company is also the external manager of a venture in which SAFE is a member. Following are the key terms of the management agreement with SAFE: ● The Company receives a fee equal to 1.0 % of total SAFE equity (as defined in the management agreement) up to $ 1.5 billion; 1.25 % of total SAFE equity (for incremental equity of $ 1.5 billion - $ 3.0 billion); 1.375 % 73 Table of Contents iStar Inc. Notes to Consolidated Financial Statements of total SAFE equity (for incremental equity of $ 3.0 billion - $ 5.0 billion); and 1.5 % of total SAFE equity (for incremental equity over $ 5.0 billion); ● Fee to be paid in cash or in shares of SAFE common stock, at the discretion of SAFE’s independent directors; ● The stock is locked up for two years , subject to certain restrictions; ● There is no additional performance or incentive fee; ● The management agreement is non-terminable by SAFE through June 30, 2023 except for cause; and ● Automatic annual renewals thereafter, subject to non-renewal upon certain findings by SAFE’s independent directors and payment of termination fee equal to three times the prior year’s management fee. During the year ended December 31, 2022, the Company purchased 0.2 million shares of SAFE's common stock for $ 10.5 million, for an average cost of $ 66.83 per share, in open market purchases made in accordance with Rules 10b5-1 and 10b-18 under the Securities and Exchange Act of 1934, as amended. In March 2022, the Company acquired 3,240,000 shares of SAFE’s common stock in a private placement for $ 191.2 million. In December 2022, the Company paid a non-cash dividend of approximately 6.63 million shares of SAFE common stock to its shareholders. During the year ended December 31, 2021, the Company purchased 1.0 million shares of SAFE's common stock for $ 69.5 million, for an average cost of $ 72.96 per share, in open market purchases made in accordance with Rules 10b5-1 and 10b-18 under the Securities and Exchange Act of 1934, as amended. In addition, in the fourth quarter 2021 the Company purchased 24,108 shares of SAFE’s common stock for $ 1.8 million, for an average cost of $ 73.86 per share, in an open market transaction. In September 2021, the Company acquired 657,894 shares of SAFE’s common stock in a private placement for $ 50.0 million. In November 2020, the Company acquired 1.1 million shares of SAFE’s common stock in a private placement for $ 65.0 million. In March 2020, the Company acquired 1.7 million shares of SAFE’s common stock in a private placement for $ 80.0 million. As of December 31, 2022, the Company owned approximately 54.3 % of SAFE’s common stock outstanding. During the years ended December 31, 2022, 2021 and 2020, the Company recorded $ 20.3 million, $ 14.9 million and $ 12.7 million, respectively, of management fees pursuant to its management agreement with SAFE. The Company is also entitled to receive certain expense reimbursements, including for the allocable costs of its personnel that perform certain legal, accounting, due diligence tasks and other services that third-party professionals or outside consultants otherwise would perform. Historically, pursuant to the Company’s option under the management agreement, the Company has elected to not seek reimbursement for certain expenses. This historical election is not a waiver of reimbursement for similar expenses in future periods and the Company has started to elect to seek, and may further seek in the future, reimbursement of such additional expenses that it has not previously sought, including, without limitation, rent, overhead and certain personnel costs. During the years ended December 31, 2022, 2021 and 2020, the Company recognized $ 12.5 million, $ 7.5 million and $ 5.0 million, respectively, of expense reimbursements pursuant to its management agreement with SAFE. The Company has an exclusivity agreement with SAFE pursuant to which it agreed, subject to certain exceptions, that it will not acquire, originate, invest in, or provide financing for a third party’s acquisition of, a Ground Lease unless it has first offered that opportunity to SAFE and a majority of its independent directors has declined the opportunity. Following is a list of investments that the Company has transacted with SAFE, all of which were approved by the Company’s and SAFE’s independent directors, for the periods presented: In October 2017, the Company closed on a 99 -year Ground Lease and a $ 80.5 million construction financing commitment to support the ground-up development of a to-be-built luxury multi-family project. The transaction included a combination of: (i) a newly created Ground Lease and a $ 7.2 million leasehold improvement allowance, which was fully 74 Table of Contents iStar Inc. Notes to Consolidated Financial Statements funded; and (ii) an $ 80.5 million leasehold first mortgage. The Company sold the Ground Lease to SAFE in September 2020 for $ 34.0 million and recognized a gain of $ 6.1 million in “Income from sales of real estate” in connection with the sale and in January 2021 sold the leasehold first mortgage to an entity in which the Company has a 53 % noncontrolling equity interest (refer to “Other strategic investments” below) for $ 63.3 million . In June 2020, Net Lease Venture II (see Note 3) acquired the leasehold interest in an office laboratory property in Honolulu, HI and simultaneously entered into a 99 year Ground Lease with SAFE. In November 2021, the Company acquired the property from Net Lease Venture II. The Company paid $ 0.6 million to its partner to acquire its equity interest in the property and assumed a $ 44.4 million mortgage on the property. The Company sold the property in the first quarter of 2022. Prior to the sale, SAFE paid $ 0.3 million to terminate a purchase option that allowed the Company to purchase the land at the expiration of the Ground Lease. In October 2020, the Company provided a $ 22.5 million loan to the ground lessee of a Ground Lease originated at SAFE. The loan was for the Ground Lease tenant’s recapitalization of an existing multi-family property. The Company received $ 2.3 million of consideration from SAFE in connection with this transaction. In February 2021, the Company provided a $ 50.0 million loan to the ground lessee of a Ground Lease originated at SAFE. The loan was for the Ground Lease tenant’s recapitalization of a hotel property. The Company received $ 1.9 million of consideration from SAFE in connection with this transaction. The Company sold the loan in July 2021 and recorded no gain or loss on the sale. In March 2021, the Company acquired land and simultaneously structured and entered into with the seller a Ground Lease on which a multi-family project will be constructed. At closing, the Company entered into an agreement with SAFE pursuant to which, subject to certain conditions being met, SAFE would acquire the ground lessor entity from the Company. The Company sold the ground lessor entity to SAFE in September 2021 and recognized no gain or loss on the sale (refer to Note 7 - Loans receivable held for sale). The Company also committed to provide a $ 75.0 million construction loan to the Ground Lease tenant. The Company received $ 2.7 million of consideration from SAFE in connection with this transaction. In September 2021, the construction loan commitment and the $ 2.7 million of consideration was transferred to the Loan Fund (refer to “Other strategic investments” below). In June 2021, the Company sold to SAFE its rights under a purchase option agreement for $ 1.2 million. The Company had previously acquired such purchase option agreement from a third-party property owner for $ 1.0 million and incurred $ 0.2 million of expenses. Under the option agreement, upon certain conditions being met by an outside developer who may become the Ground Lease tenant, SAFE has the right to acquire for $ 215.0 million a property and hold a Ground Lease under approximately 1.1 million square feet of office space that may be developed on the property. No gain or loss was recognized by the Company as a result of the sale. In June 2021, the Company and SAFE entered into two agreements pursuant to each of which SAFE would acquire land and a related Ground Lease originated by the Company when certain construction related conditions are met by a specified time period. The purchase price to be paid for each is $ 42.0 million, plus an amount necessary for the Company to achieve the greater of a 1.25 x multiple and a 9 % return on its investment. In addition, each Ground Lease provides for a leasehold improvement allowance up to a maximum of $ 83.0 million, which obligation would be assumed by SAFE upon acquisition. If certain construction conditions are not met within a specified time period, SAFE will have no obligation to acquire the Ground Leases or fund the leasehold improvement allowances. In January 2022, the Company sold the Ground Leases to the Ground Lease Plus Fund (see below). There can be no assurance that the conditions to closing will be satisfied and that SAFE will acquire the properties and Ground Leases from the Ground Lease Plus Fund. ​ In November 2021, the Company and SAFE entered into an agreement pursuant to which SAFE would acquire land and a related Ground Lease originated by the Company when certain construction related conditions are met by a specified time period. The purchase price to be paid is $ 33.3 million, plus an amount necessary for the Company to achieve the greater of a 1.25 x multiple and a 12 % return on its investment. In addition, the Ground Lease provides for a leasehold improvement allowance up to a maximum of $ 51.8 million, which obligation would be assumed by SAFE upon acquisition. If certain construction conditions are not met within a specified time period, SAFE will have no obligation to acquire the Ground Lease or fund the leasehold improvement allowance. There can be no assurance that the conditions to 75 Table of Contents iStar Inc. Notes to Consolidated Financial Statements closing will be satisfied and that SAFE will acquire the land and Ground Lease from the Ground Lease Plus Fund (refer to Ground Lease Plus Fund below) . In December 2021, the Company’s partner in a venture recapitalized an existing multifamily property, which included a Ground Lease provided by SAFE. As part of the recapitalization, the Company’s partner acquired its 50 % equity interest in the entity and the mezzanine loan held by the Company was repaid in full. During the years ended December 31, 2021 and 2020, the Company recorded $ 2.3 million and $ 2.4 million respectively, of interest income on the mezzanine loan. In January 2022, the Company and SAFE entered into an agreement pursuant to which SAFE would acquire land and a related Ground Lease originated by the Company when certain construction related conditions are met. The Company sold the Ground Lease to SAFE in July 2022 for $ 36.0 million when the construction related conditions were met and recognized a gain of $ 1.0 million in “Income from sales of real estate” in its consolidated statements of operations. In February 2022, the Loan Fund (refer to Other Strategic Investments below) committed to provide a $ 130.0 million loan to the ground lessee of a Ground Lease originated at SAFE. The loan is for the Ground Lease tenant’s recapitalization of a life science property. The Loan Fund received $ 9.0 million of consideration from SAFE in connection with this transaction. In April 2022, the Company exchanged its 50 % equity interest with a carrying value of $ 4.4 million in a venture that owned a hotel property for land underlying the property with an in-place Ground Lease valued at $ 9.0 million and recorded a gain of $ 4.6 million in “Earnings from equity method investments” in the consolidated statements of operations. Subsequently, the Company sold the Ground Lease on the land to SAFE for $ 9.0 million and did no t recognize any gain or loss on the sale. In June 2022, the Loan Fund (refer to Other Strategic Investments below) committed to provide a $ 105.0 million loan to the ground lessee of a Ground Lease originated at SAFE. The loan is for the Ground Lease tenant’s recapitalization of a mixed-use property. The Loan Fund received $ 5.0 million of consideration from SAFE in connection with this transaction. Ground Lease Plus Fund —The Company formed and manages an investment fund that targets the origination and acquisition of Ground Leases for commercial real estate projects that are in a pre-development phase (the “Ground Lease Plus Fund”). The Company owns a 53 % noncontrolling equity interest in the Ground Lease Plus Fund. The Company does not have a controlling interest in the Ground Lease Plus Fund due to the substantive participating rights of its partner and accounts for this investment as an equity method investment. In addition, the Ground Lease Plus Fund has first look rights through December 2023 on qualifying pre-development projects that SAFE has elected to not originate. In November 2021, the Company acquired land for $ 33.3 million and simultaneously structured and entered into a Ground Lease on which a multi-family project will be constructed. In December 2021, the Company sold the Ground Lease to the Ground Lease Plus Fund and recognized no gain or loss on the sale. The Company and SAFE entered into an agreement pursuant to which SAFE would acquire the land and related Ground Lease from the Ground Lease Plus Fund when certain construction related conditions are met by a specified time period (refer to “Safehold Inc.” above). In January 2022, the Company sold two Ground Leases to the Ground Lease Plus Fund (refer to Note 5) and recognized an aggregate $ 0.5 million of gains in “Income from sales of real estate” on the sale. The Company and SAFE entered into an agreement pursuant to which SAFE would acquire the land properties and related Ground Leases from the Ground Lease Plus Fund when certain construction related conditions are met by a specified time period (refer to “Safehold Inc.” above). Other real estate equity investments —As of December 31, 2022, the Company’s other real estate equity investments include equity interests of 95 % in real estate ventures comprised of investments of $ 32.4 million in three operating properties. As of December 31, 2021, the Company’s other real estate equity investments included $ 43.3 million in operating properties and $ 1.1 million in land assets. 76 Table of Contents iStar Inc. Notes to Consolidated Financial Statements In August 2018, the Company provided a mezzanine loan with a principal balance of $ 33.0 million to an unconsolidated entity in which the Company owns a 50 % equity interest. In December 2021, the Company’s partner in the venture recapitalized the existing multifamily property, which included a Ground Lease provided by SAFE. As part of the recapitalization, the Company’s partner acquired its 50 % equity interest in the entity and the mezzanine loan was repaid in full. During the years ended December 31, 2021 and 2020, the Company recorded $ 2.3 million, $ 2.4 million, respectively, of interest income on the mezzanine loan. Other strategic investments —As of December 31, 2022 and 2021, the Company also had investments in real estate related funds and other strategic investments in real estate entities. In January 2021, the Company sold two loans for $ 83.4 million to a newly formed entity in which the Company owns a 53.0 % noncontrolling equity interest (the “Loan Fund”). The Company did no t recognize any gain or loss on the sales. In September 2021, the Company transferred a $ 75.0 million construction loan commitment to the Loan Fund. The Company does not have a controlling interest in the Loan Fund due to the substantive participating rights of its partner. The Company accounts for this investment as an equity method investment and receives a fixed annual fee in exchange for managing the entity. In February 2022, the Loan Fund committed to provide a $ 130.0 million loan to the ground lessee of a Ground Lease originated at SAFE. The loan was for the Ground Lease tenant’s recapitalization of a life science property. In June 2022, the Loan Fund committed to provide a $ 105.0 million loan to the ground lessee of a Ground Lease originated at SAFE. The loan was for the Ground Lease tenant’s recapitalization of a mixed-use property. Summarized investee financial information — The following table presents the investee level summarized financial information of the Company’s equity method investments ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ As of December 31, ​ For the Years Ended December 31, ​ 2022 2021 ​ 2022 2021 2020 Balance Sheets ​ ​ ​ ​ ​ ​ ​ Income Statements ​ ​ ​ ​ ​ ​ ​ ​ ​ Total assets ​ $ 6,124,451 ​ $ 6,107,890 ​ Revenues ​ $ 640,429 ​ $ 889,131 ​ $ 129,789 Total liabilities ​ 3,754,720 ​ 3,019,208 ​ Expenses ​ ( 237,671 ) ​ ( 254,001 ) ​ ( 188,605 ) Noncontrolling interests ​ 23,587 ​ 3,024 ​ Net income (loss) attributable to parent entities ​ 393,492 ​ 634,896 ​ ( 59,010 ) Total equity attributable to parent entities ​ 2,346,143 ​ 3,085,657 ​ ​ ​ ​ ​ During the years ended December 31, 2022, 2021 and 2020, SAFE represented a significant subsidiary of the Company. For detailed financial information regarding SAFE, please refer to its financial statements, which are publicly available on the website of the Securities and Exchange Commission at http://www.sec.gov under the ticker symbol "SAFE" and are incorporated herein by reference. 77 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Note 9—Other Assets and Other Liabilities Deferred expenses and other assets, net, consist of the following items ($ in thousands): (1) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ As of ​ ​ December 31, 2022 December 31, 2021 ​ Intangible assets, net (2) ​ $ 319 ​ $ 1,209 ​ Restricted cash ​ 6,423 ​ 54,395 ​ Operating lease right-of-use assets (3) ​ 16,110 ​ 20,437 ​ Other assets (4) ​ 19,009 ​ 16,040 ​ Other receivables ​ 2,845 ​ 5,054 ​ Leasing costs, net (5) ​ 129 ​ 818 ​ Corporate furniture, fixtures and equipment, net (6) ​ 1,441 ​ 1,852 ​ Deferred financing fees, net ​ — ​ 629 ​ Deferred expenses and other assets, net ​ $ 46,276 ​ $ 100,434 ​ (1) Certain items have been reclassified to “Real estate and other assets available and held for sale and classified as discontinued operations” (refer to Note 3). (2) Intangible assets, net includes above market and in-place lease assets and lease incentives related to the acquisition of real estate assets. Accumulated amortization on intangible assets, net was $ 0.1 million and $ 10.2 million as of December 31, 2022 and 2021, respectively. The amortization of above market leases and lease incentive assets decreased operating lease income in the Company’s consolidated statements of operations by $ 0.1 million, $ 0.3 million and $ 0.2 million for the years ended December 31, 2022, 2021 and 2020, respectively. These intangible lease assets are amortized over the remaining term of the lease. The amortization expense for in-place leases was $ 0.1 million, $ 1.0 million and $ 0.2 million for the years ended December 31, 2022, 2021 and 2020, respectively. These amounts are included in “Depreciation and amortization” in the Company’s consolidated statements of operations. As of December 31, 2022, the weighted average remaining amortization period for the Company’s intangible assets was approximately 5.8 years. (3) Right-of-use lease assets relate primarily to the Company’s leases of office space and certain other leases. Right-of use lease assets initially equal the lease liability. The lease liability (see table below) equals the present value of the minimum rental payments due under the lease discounted at the rate implicit in the lease or the Company's incremental secured borrowing rate for similar collateral. For operating leases, rent expense is recognized on a straight-line basis over the term of the lease and is recorded in “General and administrative” and “Real estate expense” in the Company’s consolidated statements of operations. During the years ended December 31, 2022, 2021 and 2020, the Company recognized $ 4.8 million, $ 4.9 million and $ 4.7 million, respectively, in “General and administrative” and $ 0.7 million, $ 0.6 million and $ 0.6 million, respectively, in “Real estate expense” in its consolidated statements of operations relating to operating leases. (4) Other assets primarily includes prepaid expenses, deposits for certain real estate assets and management fees and expense reimbursements due from SAFE (refer to Note 8). (5) Accumulated amortization of leasing costs was $ 0.1 million and $ 1.1 million as of December 31, 2022 and 2021, respectively. (6) Accumulated depreciation on corporate furniture, fixtures and equipment was $ 12.3 million and $ 14.8 million as of December 31, 2022 and 2021, respectively. Accounts payable, accrued expenses and other liabilities consist of the following items ($ in thousands): (1) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ As of ​ ​ December 31, 2022 December 31, 2021 ​ Other liabilities (2) ​ $ 29,375 ​ ​ 30,362 ​ Accrued expenses ​ 70,445 ​ 151,810 ​ Operating lease liabilities (see table above) ​ 17,645 ​ 23,267 ​ Accrued interest payable ​ 26,012 ​ 31,293 ​ Accounts payable, accrued expenses and other liabilities ​ $ 143,477 ​ $ 236,732 ​ (1) Certain items have been reclassified to “Liabilities associated with real estate held for sale and classified as discontinued operations” (refer to Note 3). (2) As of December 31, 2022 and 2021, "Other liabilities" includes $ 21.2 million and $ 20.1 million, respectively, of deferred income. As of December 31, 2021, other liabilities includes $ 0.1 million of expected credit losses for unfunded loan commitments. ​ ​ ​ ​ ​ 78 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Note 10—Debt Obligations, net The Company’s debt obligations were as follows ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Carrying Value as of ​ Stated ​ Scheduled ​ December 31, 2022 December 31, 2021 Interest Rates Maturity Date Secured credit facilities: ​ ​ ​ Revolving Credit Facility ​ $ — ​ $ — ​ LIBOR + 2.00 % (1) — Senior Term Loan ​ — ​ 491,875 ​ LIBOR + 2.75 % (2) — Total secured credit facilities ​ — ​ 491,875 ​ Unsecured notes: ​ ​ ​ 3.125 % senior convertible notes (3) ​ — ​ 287,500 ​ 3.125 % — 4.75 % senior notes (4) ​ 753,561 ​ 775,000 ​ 4.75 % October 2024 4.25 % senior notes (5) ​ 501,997 ​ 550,000 ​ 4.25 % August 2025 5.50 % senior notes (6) ​ 346,906 ​ 400,000 ​ 5.50 % February 2026 Total unsecured notes ​ 1,602,464 ​ 2,012,500 ​ Other debt obligations: ​ ​ ​ Trust preferred securities ​ 100,000 ​ 100,000 ​ LIBOR + 1.50 % October 2035 Total debt obligations ​ 1,702,464 ​ 2,604,375 ​ Debt discounts and deferred financing costs, net ​ ( 19,943 ) ​ ( 32,201 ) ​ Total debt obligations, net (7) ​ $ 1,682,521 ​ $ 2,572,174 ​ (1) The Revolving Credit Facility accrued interest at the Company’s election of either: (i) a base rate, which is the greater of (a) prime, (b) federal funds plus 0.50 % or (c) LIBOR plus 1.00 % and subject to a margin ranging from 1.00 % to 1.50 % ; or (ii) LIBOR subject to a margin ranging from 2.00 % to 2.50 % . The Company terminated the Revolving Credit Facility in August 2022. (2) The loan accrued interest at the Company’s election of either: (i) a base rate, which is the greater of (a) prime, (b) federal funds plus 0.50 % or (c) LIBOR plus 1.00 % and subject to a margin of 1.75 % ; or (ii) LIBOR subject to a margin of 2.75 % . (3) During the years ended December 31, 2022, 2021 and 2020, the Company recognized $ 3.5 million, $ 9.0 million, $ 9.0 million, respectively, of contractual interest on the 3.125 % Convertible Notes . Refer to Unsecured Notes below. (4) The Company can prepay these senior notes without penalty beginning July 1, 2024. (5) The Company can prepay these senior notes without penalty beginning May 1, 2025. (6) The Company can prepay these senior notes without penalty beginning August 15, 2024. (7) The Company capitalized interest relating to development activities of $ 1.5 million, $ 1.0 million and $ 1.4 million for the years ended December 31, 2022, 2021 and 2020, respectively. Future Scheduled Maturities — As of December 31, 2022, future scheduled maturities of outstanding debt obligations are as follows ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Unsecured Debt Secured Debt Total 2023 ​ $ — ​ $ — ​ $ — 2024 ​ 753,561 ​ — ​ 753,561 2025 ​ 501,997 ​ — ​ 501,997 2026 ​ 346,906 ​ — ​ 346,906 2027 ​ — ​ — ​ — Thereafter ​ 100,000 ​ — ​ 100,000 Total principal maturities ​ 1,702,464 ​ — ​ 1,702,464 Unamortized discounts and deferred financing costs, net ​ ( 19,943 ) ​ — ​ ( 19,943 ) Total debt obligations, net ​ $ 1,682,521 ​ $ — ​ $ 1,682,521 ​ Senior Term Loan —The Company had a $ 650.0 million senior term loan that accrued interest at LIBOR plus 2.75 % per annum and matured in June 2023 (the “Senior Term Loan”). The Senior Term Loan was secured by pledges of equity of certain subsidiaries that own a defined pool of assets. The Senior Term Loan permitted substitution of collateral, subject to overall collateral pool coverage and concentration limits, over the life of the facility. The Company repaid the Senior Term Loan in full in March 2022 using proceeds from the Net Lease Sale (refer to Note 3 - Net Lease Sale and 79 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Discontinued Operations). During the year ended December 31, 2022, the Company incurred a “Loss on extinguishment of debt” of $ 1.4 million in connection with the repayment of the Senior Term Loan. Revolving Credit Facility —The Company had a secured revolving credit facility with a maximum capacity of $ 350.0 million and a maturity of September 2022 (the “Revolving Credit Facility”). The Company terminated the Revolving Credit Facility in August 2022. Outstanding borrowings under the Revolving Credit Facility were secured by pledges of the equity interests in the Company’s subsidiaries that own a defined pool of assets. Borrowings under this credit facility accrued interest at a floating rate indexed to one of several base rates plus a margin which adjusted upward or downward based upon the Company’s corporate credit rating, ranging from 1.0 % to 1.5 % in the case of base rate loans and from 2.0 % to 2.5 % in the case of LIBOR loans. In addition, there was an undrawn credit facility commitment fee that ranges from 0.25 % to 0.45 %, based on corporate credit ratings. Unsecured Notes — As of December 31, 2022, the Company has senior unsecured notes outstanding with varying fixed-rates and maturities ranging from October 2024 to February 2026. In connection with the Net Lease Sale, in the fourth quarter 2021, the Company obtained the consents of holders of its outstanding 4.75 % senior notes due 2024, 4.25 % senior notes due 2025 and 5.50 % senior notes due 2026 to certain amendments to the indentures governing the notes intended to align the indentures with the sale of the Company's net lease assets. The Company paid holders consent fees ranging from 0.75 % to 1.00 % of the principal amount of consenting notes, depending on the relevant series. The Company’s senior unsecured notes are interest only, are generally redeemable at the option of the Company and contain certain financial covenants (see below). 3.125 % Senior Convertible Notes —In April 2022, the Company completed separate, privately-negotiated transactions with holders of $ 194 million aggregate principal amount of the Company's 3.125 % Convertible Notes in which the noteholders exchanged their convertible notes with the Company for 13.75 million newly issued shares of the Company's common stock and aggregate cash payments of $ 14 million. The 3.125 % Convertible Senior Notes received by the Company were retired. The Company applied extinguishment accounting and recognized a net increase in shareholders’ equity of $ 180.6 million inclusive of a $ 118.1 million loss on extinguishment of debt in connection with these transactions. In July and August 2022, the Company completed a series of privately-negotiated exchange transactions with holders of approximately $ 80.9 million aggregate principal amount of the Company's 3.125 % Convertible Notes in which the noteholders exchanged their convertible notes with the Company for an aggregate of approximately 3.3 million newly issued shares of the Company's common stock and aggregate cash payments of approximately $ 43.6 million inclusive of accrued interest. The convertible notes received by the Company were retired. The Company applied extinguishment accounting and recognized a net increase in shareholders’ equity of $ 38.2 million inclusive of a $ 12.1 million loss on extinguishment of debt in connection with these transactions. In September 2022, the holders of approximately $ 11.7 million aggregate principal amount of the Company's 3.125 % Convertible Notes executed their conversion rights under the notes and exchanged their convertible notes with the Company for an aggregate of approximately 92,011 newly issued shares of the Company's common stock and aggregate cash payments of approximately $ 11.7 million. The convertible notes received by the Company were retired. The Company also repaid $ 0.5 million principal amount of its 3.125 % Convertible Notes for cash at maturity. 4.75 % Senior Notes —In April 2022, the Company redeemed $ 7.1 million principal amount of its 4.75 % senior notes due October 2024 for $ 7.2 million. The Company recognized a $ 0.2 million loss on extinguishment of debt in connection with these transactions. In July and August 2022, the Company redeemed an aggregate $ 14.4 million principal amount of its senior notes due October 2024 for $ 14.5 million. The Company recognized a $ 0.3 million net loss on extinguishment of debt in connection with these transactions. 5.50 % Senior Notes —In June 2022, the Company redeemed $ 53.1 million principal amount of its 5.50 % senior notes due February 2026 for $ 50.6 million. The Company recognized a $ 1.7 million net gain on extinguishment of debt in connection with these transactions. 80 Table of Contents iStar Inc. Notes to Consolidated Financial Statements 4.25 % Senior Notes — In August and September 2022, the Company redeemed an aggregate $ 48.0 million principal amount of its senior notes due August 2025 for $ 48.1 million. The Company recognized a $ 0.7 million loss on extinguishment of debt in connection with these transactions. Debt Covenants The Company’s outstanding unsecured debt securities contain corporate level covenants that include a covenant to maintain a ratio of unencumbered assets to unsecured indebtedness, as such terms are defined in the indentures governing the debt securities, of at least 1.3 x and a covenant restricting certain incurrences of debt based on a fixed charge coverage ratio. If any of the Company’s covenants are breached and not cured within applicable cure periods, the breach could result in acceleration of its debt securities unless a waiver or modification is agreed upon with the requisite percentage of the bondholders. Note 11—Commitments and Contingencies Unfunded Commitments —The Company generally funds construction and development loans and build-outs of space in real estate assets over a period of time if and when the borrowers and tenants meet established milestones and other performance criteria. The Company refers to these arrangements as Performance-Based Commitments. As of December 31, 2022, the maximum amount of fundings the Company may be required to make under each category, assuming all performance hurdles and milestones are met under the Performance-Based Commitments are as follows ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Other ​ Investments Performance-Based Commitments ​ $ 146,560 ​ Other Commitments —Total operating lease expense for the years ended December 31, 2022, 2021 and 2020 was $ 5.2 million, $ 5.2 million and $ 5.4 million, respectively. Future minimum lease obligations under non-cancelable operating leases, excluding lease obligations for liabilities included in discontinued operations, as of December 31, 2022 are as follows ($ in thousands): ​ ​ ​ ​ ​ ​ Operating (1) 2023 ​ $ 6,295 2024 ​ 6,178 2025 ​ 6,166 2026 ​ 142 2027 ​ 162 Thereafter ​ — Total undiscounted cash flows ​ 18,943 Present value discount (1) ​ ( 1,298 ) Lease liabilities ​ $ 17,645 (1) The lease liability equals the present value of the minimum rental payments due under the lease discounted at the rate implicit in the lease or the Company’s incremental secured borrowing rate for similar collateral. For operating leases, lease liabilities were discounted at the Company’s weighted average incremental secured borrowing rate for similar collateral estimated to be 4.7 % and the weighted average remaining lease term is 3.7 years. ​ Legal Proceedings —The Company and/or one or more of its subsidiaries is party to various pending litigation matters that are considered ordinary routine litigation incidental to the Company’s business as a finance and investment company focused on the commercial real estate industry, including foreclosure-related proceedings. The Company believes it is not a party to, nor are any of its properties the subject of, any pending legal proceeding that would have a material adverse effect on the Company’s consolidated financial statements. 81 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Note 12—Risk Management and Derivatives Risk management In the normal course of its on-going business operations, the Company encounters economic risk. There are three main components of economic risk: interest rate risk, credit risk and market risk. The Company is subject to interest rate risk to the degree that its interest-bearing liabilities mature or reprice at different points in time and potentially at different bases, than its interest-earning assets. Credit risk is the risk of default on the Company’s lending investments or leases that result from a borrower’s or tenant’s inability or unwillingness to make contractually required payments. Market risk reflects changes in the value of loans and other lending investments due to changes in interest rates or other market factors, including the rate of prepayments of principal and the value of the collateral underlying loans, the valuation of real estate assets by the Company as well as changes in foreign currency exchange rates. Risk concentrations —Concentrations of credit risks arise when a number of borrowers or tenants related to the Company’s investments are engaged in similar business activities, or activities in the same geographic region, or have similar economic features that would cause their ability to meet contractual obligations, including those to the Company, to be similarly affected by changes in economic conditions. Substantially all of the Company’s real estate and net investment in leases, including those classified in real estate and other assets available and held for sale and classified as discontinued operations, and assets collateralizing its loans receivable are located in the United States. As of December 31, 2022, the Company’s portfolio contains concentrations in the following property types: Ground Leases, land and development, multifamily, hotel, entertainment/leisure, condominium, retail and other property types. The Company underwrites the credit of prospective borrowers and tenants and often requires them to provide some form of credit support such as corporate guarantees, letters of credit and/or cash security deposits. Although the Company’s loans and real estate assets are geographically diverse and the borrowers and tenants operate in a variety of industries, to the extent the Company has a significant concentration of interest or operating lease revenues from any single borrower or tenant, the inability of that borrower or tenant to make its payment could have a material adverse effect on the Company. Derivatives The Company’s use of derivative financial instruments has historically been limited to the utilization of interest rate swaps, interest rate caps and foreign exchange contracts. The principal objective of such financial instruments is to minimize the risks and/or costs associated with the Company’s operating and financial structure and to manage its exposure to interest rates and foreign exchange rates. The Company may have derivatives that are not designated as hedges because they do not meet the strict hedge accounting requirements. Although not designated as hedges, such derivatives are entered into to manage the Company’s exposure to interest rate movements and other identified risks. 82 Table of Contents iStar Inc. Notes to Consolidated Financial Statements The Company did not have any derivative financial instruments as of December 31, 2022. The table below presents the fair value of the Company’s derivative financial instruments as well as their classification on the consolidated balance sheets as of December 31, 2021 ($ in thousands): (1) ​ ​ ​ ​ ​ ​ ​ ​ Derivative Liabilities ​ ​ Balance Sheet ​ Fair As of December 31, 2021 Location Value Derivatives Designated in Hedging Relationships ​ Interest rate swaps Liabilities associated with real estate held for sale and classified as discontinued operations ​ $ 8,395 Total ​ $ 8,395 (1) Over the next 12 months, the Company expects that $ 2.0 million related to its proportionate share of cash flow hedges held by SAFE will be reclassified from “Accumulated other comprehensive income (loss)” as a decrease to earnings from equity method investments. The table below presents the effect of the Company’s derivative financial instruments, including the Company’s share of derivative financial instruments at certain of its equity method investments, in the consolidated statements of operations and the consolidated statements of comprehensive income (loss) ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Amount of Gain Amount of Gain ​ ​ Location of Gain ​ (Loss) Recognized in ​ (Loss) Reclassified ​ ​ (Loss) ​ Accumulated Other ​ from Accumulated Derivatives Designated in ​ When Recognized in ​ Comprehensive ​ Other Comprehensive Hedging Relationships Income Income Income into Earnings For the Year Ended December 31, 2022 ​ ​ ​ ​ ​ ​ ​ ​ Interest rate swaps Earnings from equity method investments ​ $ 20,317 ​ $ ( 7,737 ) For the Year Ended December 31, 2021 ​ ​ Interest rate swaps Net income from discontinued operations ​ $ 4,748 ​ $ ( 8,140 ) Interest rate swaps Earnings from equity method investments ​ 8,638 ​ ( 1,943 ) For the Year Ended December 31, 2020 ​ ​ Interest rate swaps Net income from discontinued operations ​ $ ( 14,940 ) ​ $ ( 6,974 ) Interest rate swaps Earnings from equity method investments ​ ( 13,350 ) ​ ( 1,101 ) ​ 83 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Note 13—Equity Preferred Stock —The Company had the following series of Cumulative Redeemable Preferred Stock outstanding as of December 31, 2022 and 2021: ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Cumulative Preferential Cash ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Dividends (1)(2) ​ ​ ​ ​ ​ ​ Shares Issued ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ and ​ ​ ​ ​ ​ ​ ​ ​ ​ Annual ​ Carrying ​ ​ ​ Outstanding ​ Par ​ Liquidation ​ Rate per ​ Dividend ​ Value ​ Series (in thousands) Value Preference (3) Annum per share (in thousands) ​ D 4,000 ​ $ 0.001 ​ $ 25.00 8.00 % $ 2.00 ​ $ 89,041 ​ G 3,200 ​ 0.001 ​ 25.00 7.65 % 1.91 ​ 72,664 ​ I 5,000 ​ 0.001 ​ 25.00 7.50 % 1.88 ​ 120,785 ​ Total 12,200 ​ ​ ​ ​ ​ ​ ​ ​ $ 282,490 ​ (1) Holders of shares of the Series D, G and I preferred stock are entitled to receive dividends, when and as declared by the Company’s Board of Directors, out of funds legally available for the payment of dividends. Dividends are cumulative from the date of original issue and are payable quarterly in arrears on or before the 15th day of each March, June, September and December or, if not a business day, the next succeeding business day. Any dividend payable on the preferred stock for any partial dividend period will be computed on the basis of a 360 - day year consisting of twelve 30 - day months. Dividends will be payable to holders of record as of the close of business on the first day of the calendar month in which the applicable dividend payment date falls or on another date designated by the Company’s Board of Directors for the payment of dividends that is not more than 30 nor less than 10 days prior to the dividend payment date. (2) The Company declared and paid dividends of $ 8.0 million, $ 6.1 million and $ 9.4 million on its Series D, G and I Cumulative Redeemable Preferred Stock during both the years ended December 31, 2022 and 2021, respectively. The character of the 2022 dividends was 100 % capital gain distribution. The character of the 2021 dividends was 100 % capital gain distribution, of which 18.31 % represented unrecaptured section 1250. There are no dividend arrearages on any of the preferred shares currently outstanding. (3) The Company may, at its option, redeem the Series G and I Preferred Stock, in whole or in part, at any time and from time to time, for cash at a redemption price equal to 100 % of the liquidation preference of $ 25.00 per share, plus accrued and unpaid dividends, if any, to the redemption date. Dividends —To maintain its qualification as a REIT, the Company must annually distribute, at a minimum, an amount equal to 90% of its taxable income, excluding net capital gains, and must distribute 100% of its taxable income (including net capital gains) to eliminate corporate federal income taxes payable by the REIT. The Company has recorded NOLs in the past and may record NOLs in the future, which may reduce its taxable income in future periods and lower or eliminate entirely the Company’s obligation to pay dividends for such periods in order to maintain its REIT qualification. As of December 31, 2021, the Company had $ 614.6 million of NOL carryforwards at the corporate REIT level that can generally be used to offset both ordinary taxable income and capital gain net income in future years. In its year ended December 31, 2022, the Company expects to report REIT taxable income before the deduction for dividends paid and will fully utilize its NOL carryforward. Because taxable income differs from cash flow from operations due to non-cash revenues and expenses (such as depreciation and certain asset impairments), in certain circumstances, the Company may generate operating cash flow in excess of its dividends, or alternatively, may need to make dividend payments in excess of operating cash flows. The Company declared common stock dividends of $ 31.8 million, or $ 0.375 per share, for the year ended December 31, 2022 and $ 35.1 million, or $ 0.485 per share, for the year ended December 31, 2021. The Company designated all of its 2022 dividends as a capital gain distribution. The character of the 2021 dividends was 100 % capital gain distribution, of which 18.31 % represented unrecaptured section 1250 gain. In addition, in December 2022 the Company paid a dividend of 6.63 million shares of SAFE common stock, or $ 2.19 per share of the Company’s common stock, to its shareholders. Stock Repurchase Program —The Company may repurchase shares in negotiated transactions or open market transactions, including through one or more trading plans. The Company did not repurchase any shares of its common stock during the year ended December 31, 2022. During the year ended December 31, 2021, the Company repurchased 5.5 million shares of its outstanding common stock for $ 122.4 million, for an average cost of $ 22.38 per share. During the year ended December 31, 2020, the Company repurchased 4.2 million shares of its outstanding common stock for $ 48.4 million, for an average cost of $ 11.48 per share. The Company is generally authorized to repurchase up to $ 50.0 million in shares of its common stock. As of December 31, 2022, the Company had remaining authorization to repurchase up to $ 50.0 million of common stock under its stock repurchase program. 84 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Accumulated Other Comprehensive Income (Loss) —"Accumulated other comprehensive income (loss)” reflected in the Company’s shareholders’ equity is comprised of the following ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ As of ​ ​ December 31, 2022 December 31, 2021 ​ Unrealized gains on available-for-sale securities ​ $ — $ 4,237 ​ Unrealized gains (losses) on cash flow hedges ​ 2,230 ​ ( 25,824 ) ​ Accumulated other comprehensive income (loss) ​ $ 2,230 ​ $ ( 21,587 ) ​ ​ ​ ​ Note 14—Stock-Based Compensation Plans and Employee Benefits Stock-Based Compensation —The Company recorded stock-based compensation expense, including the expense related to performance incentive plans (see below), of ($ 27.7 ) million, $ 69.3 million and $ 39.4 million, respectively, during the years ended December 31, 2022, 2021 and 2020 in "General and administrative" in the Company’s consolidated statements of operations. As of December 31, 2022, there was $ 5.2 million of total unrecognized compensation cost related to all unvested restricted stock units that is expected to be recognized over a weighted average remaining vesting/service period of 1.08 years. Performance Incentive Plans —The Company’s Performance Incentive Plans ("iPIP") are designed to provide, primarily to senior executives and select professionals engaged in the Company’s investment activities, long-term compensation which has a direct relationship to the realized returns on investments included in the plans. Awards vest over six years , with 40 % being vested at the end of the second year and 15 % each year thereafter. As of December 31, 2022, there are five iPIP Plans, each covering a two-year investment period beginning with the 2013-2014 Plan through the 2021-2022 Plan. 2019-2022 iPIP Plans —The Company’s 2019-2020 and 2021-2022 iPIP plans are equity-classified awards which are measured at the grant date fair value and recognized as compensation cost in "General and administrative" in the Company’s consolidated statements of operations and "Noncontrolling interests" in the Company’s consolidated statements of changes in equity over the requisite service period. Investments in the 2019-2022 iPIP plans will be held by consolidated subsidiaries of the Company and have two ownership classes, class A units and class B units. The Company owns 100 % of the class A units and the class B units were issued to employees as long-term compensation. Except for certain clawback provisions, participants can retain vested class B units upon their termination of employment with the Company. The class B units are entitled to distributions from the net cash realized from the investments in the plan after the Company, through its ownership of the class A units, has received a specified return on its invested capital and a return of its invested capital. Distributions on the class B units are also subject to reductions under a total shareholder return ("TSR") adjustment. The fair value of the class B units was determined using a model that forecasts the underlying cash flows from the investments within the entity to which the class B units have ownership rights. During the years ended December 31, 2022, 2021 and 2020, the Company recorded $ 4.6 million, $ 3.8 million and $ 3.4 million, respectively, of expense related to the 2019-2022 iPIP plans. Distributions on the class B units are expected to be 50 % in cash and 50 % in shares of the Company’s common stock; provided, however, that (a) the cash portion will be increased if the Company does not have sufficient shares available under shareholder approved equity plans; and (b) if the principal remaining material asset in a plan is unsold SAFE shares, the Company may elect to distribute SAFE shares in lieu of cash and Company stock. The following is a summary of the status of the Company’s equity-classified iPIP plans and changes during the year ended December 31, 2022. ​ ​ ​ ​ ​ ​ ​ iPIP Investment Pool ​ 2019-2020 2021-2022 Points at beginning of period 95.20 84.75 Granted ​ — ​ 7.95 Forfeited — ( 0.95 ) Points at end of period 95.20 91.75 ​ 85 Table of Contents iStar Inc. Notes to Consolidated Financial Statements As of December 31, 2022, investments with an aggregate gross book value of $ 764 million, including 26.7 million shares of SAFE common stock acquired by the Company, were attributable to the 2019-2020 Plan and investments with an aggregate gross book value of $ 406 million, including 5.0 million shares of SAFE common stock acquired by the Company, were attributable to the 2021-2022 Plan. 2013-2018 iPIP Plans —The remainder of the Company’s iPIP plans, as shown in the table below, are liability-classified awards and are remeasured each reporting period at fair value until the awards are settled. Certain employees will be granted awards that entitle employees to receive the residual cash flows from the investments in the plans after the Company has received a specified return on its invested capital and a return of its invested capital. Awards are also subject to reductions under a TSR adjustment. The fair value of awards is determined using a model that forecasts the Company’s projected investment performance. Settlement of the awards will be 50 % in cash and 50 % in shares of the Company’s common stock or in shares of SAFE’s common stock owned by the Company. The following is a summary of the status of the Company’s liability-classified iPIP plans and changes during the year ended December 31, 2022. ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ iPIP Investment Pool ​ 2013 ‑ 2014 2015 ‑ 2016 2017 ‑ 2018 Points at beginning of period 80.17 70.40 75.34 Granted ​ — ​ — ​ — Points at end of period 80.17 70.40 75.34 ​ During the years ended December 31, 2022, 2021 and 2020, the Company recorded ($ 38.3 ) million, $ 58.2 million and $ 30.7 million, respectively, of expense related to the 2013-2018 iPIP plans. The reduction in expense for the year ended December 31, 2022 was primarily due to a decrease in the price per share of SAFE common stock. As of December 31, 2022, investments with an aggregate gross book value of $ 13 million were attributable to the 2013-2014 Plan and investments with an aggregate gross book value of $ 159 million, including 7.6 million shares of SAFE common stock acquired by the Company, were attributable to the 2017-2018 Plan. As of December 31, 2022 there were no investments attributable to the 2015-2016 Plan. During the year ended December 31, 2022, the Company made distributions to participants in the 2013-2014 investment pool. The iPIP participants received total distributions in the amount of $ 19.6 million as compensation, comprised of cash and 412,041 shares of the Company’s common stock with a fair value of $ 16.06 per share, which are fully-vested and issued under the 2009 LTIP. After deducting statutory minimum tax withholdings, a total of 215,657 shares of the Company’s common stock were issued. During the year ended December 31, 2022, the Company made distributions to participants in the 2015-2016 investment pool. The iPIP participants received total distributions in the amount of $ 19.2 million as compensation, comprised of cash and 402,731 shares of the Company’s common stock with a fair value of $ 16.06 per share, which are fully-vested and issued under the 2009 LTIP. After deducting statutory minimum tax withholdings, a total of 193,416 shares of the Company’s common stock were issued. During the year ended December 31, 2021, the Company made distributions to participants in the 2015-2016 investment pool. The iPIP participants received total distributions in the amount of $ 10.7 million as compensation, comprised of cash and 243,044 shares of the Company’s common stock with a fair value of $ 22.66 per share, which are fully-vested and issued under the 2009 LTIP (see below). After deducting statutory minimum tax withholdings, a total of 131,757 shares of the Company’s common stock were issued. During the year ended December 31, 2020, the Company made distributions to participants in the 2015-2016 investment pool. The iPIP participants received total distributions in the amount of $ 1.5 million as compensation, comprised of cash and 54,245 shares of the Company’s common stock with a fair value of $ 14.51 per share, which are fully-vested and issued under the 2009 LTIP (see below). After deducting statutory minimum tax withholdings, a total of 32,825 shares of the Company’s common stock were issued. 86 Table of Contents iStar Inc. Notes to Consolidated Financial Statements As of December 31, 2022 and 2021, the Company had accrued compensation costs relating to iPIP of $ 45.8 million and $ 116.6 million, respectively, which are included in “Accounts payable, accrued expenses and other liabilities” on the Company’s consolidated balance sheets. Long-Term Incentive Plan —The Company’s 2009 Long-Term Incentive Plan (the “2009 LTIP”) is designed to provide incentive compensation for officers, key employees, directors and advisors of the Company. The 2009 LTIP provides for awards of stock options, shares of restricted stock, phantom shares, restricted stock units, dividend equivalent rights and other share-based performance awards. All awards under the 2009 LTIP are made at the discretion of the Company’s Board of Directors or a committee of the Board of Directors. The Company’s shareholders approved the 2009 LTIP in 2009 and approved the performance-based provisions of the 2009 LTIP, as amended, in 2014. In May 2021, the Company’s shareholders approved an increase in the number of shares available for issuance under the 2009 LTIP from a maximum of 8.9 million to 9.9 million and extended the expiration date of the 2009 LTIP from May 2029 to May 2031. As of December 31, 2022, an aggregate of 2.3 million shares remain available for issuance pursuant to future awards under the Company’s 2009 LTIP. Restricted Stock Units — Changes in non-vested restricted stock units (“Units”) during the year ended December 31, 2022 were as follows (number of shares and $ in thousands, except per share amounts): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Grant Date ​ Aggregate ​ ​ Number ​ Fair Value ​ Intrinsic ​ ​ of Shares ​ Per Share ​ Value Nonvested at beginning of period ​ 754 ​ $ 14.67 ​ $ 19,480 Granted ​ 221 ​ $ 24.77 ​ ​ Vested ​ ( 316 ) ​ $ 11.14 ​ ​ Forfeited ​ ( 25 ) ​ $ 20.54 ​ ​ ​ Nonvested at end of period 634 ​ $ 19.74 ​ $ 4,833 ​ The total fair value of Units vested during the years ended December 31, 2022, 2021 and 2020 was $ 7.3 million, $ 1.7 million and $ 3.6 million, respectively. The weighted average grant date fair value per share of Units granted during the years ended December 31, 2022, 2021 and 2020 was $ 24.77 , $ 18.59 and $ 14.68 , respectively. Directors’ Awards —Non-employee directors are awarded CSEs or restricted share awards at the time of the annual shareholders’ meeting in consideration for their services on the Company’s Board of Directors. During the year ended December 31, 2022, the Company awarded to non-employee Directors 38,953 restricted shares of common stock at a fair value per share of $ 16.33 at the time of grant for their annual equity awards and also issued 29,377 common stock equivalents ("CSEs") at a fair value of $ 8.28 per CSE in respect of dividend equivalents on outstanding CSEs. Dividends will accrue as and when dividends are declared by the Company on shares of its common stock, but will not be paid unless and until the CSEs and restricted shares of common stock vest and are settled. As of December 31, 2022, a combined total of 160,040 CSEs and restricted shares of common stock granted to members of the Company’s Board of Directors remained outstanding under the Company’s Non-Employee Directors Deferral Plan, with an aggregate intrinsic value of $ 1.2 million. 401(k) Plan —The Company has a savings and retirement plan (the "401(k) Plan"), which is a voluntary, defined contribution plan. All employees are eligible to participate in the 401(k) Plan following completion of three months of continuous service with the Company. Each participant may contribute on a pretax basis up to the maximum percentage of compensation and dollar amount permissible under Section 402(g) of the Internal Revenue Code not to exceed the limits of Code Sections 401(k), 404 and 415. At the discretion of the Company’s Board of Directors, the Company may make matching contributions on the participant’s behalf of up to 50 % of the participant’s contributions, up to a maximum of 10 % of the participants’ compensation. The Company made gross contributions of $ 1.1 million, $ 0.9 million and $ 1.1 million, respectively, for the years ended December 31, 2022, 2021 and 2020. 87 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Note 15—Earnings Per Share Earnings per share ("EPS") is calculated using the two-class method, which allocates earnings among common stock and participating securities, if applicable, to calculate EPS when an entity’s capital structure includes either two or more classes of common stock or common stock and participating securities. The following table presents a reconciliation of income (loss) allocable to common shareholders used in the basic and diluted EPS calculations ($ in thousands, except for per share data): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ For the Years Ended December 31, ​ ​ 2022 2021 2020 Net income (loss) from continuing operations ​ $ ( 197,274 ) ​ $ 16,574 ​ $ ( 116,308 ) Net loss (income) from continuing operations attributable to noncontrolling interests ​ ( 37 ) ​ 75 ​ ( 337 ) Preferred dividends ​ ( 23,496 ) ​ ( 23,496 ) ​ ( 23,496 ) Net loss from continuing operations and allocable to common shareholders for basic and diluted earnings per common share ​ $ ( 220,807 ) ​ $ ( 6,847 ) ​ $ ( 140,141 ) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ For the Years Ended December 31, ​ ​ 2022 2021 2020 Earnings allocable to common shares: ​ ​ ​ ​ Numerator for basic and diluted earnings per share: ​ ​ ​ ​ Net loss from continuing operations and allocable to common shareholders ​ $ ( 220,807 ) ​ $ ( 6,847 ) ​ $ ( 140,141 ) Net income from discontinued operations ​ ​ 797,688 ​ ​ 121,452 ​ ​ 85,455 Net (income) from discontinued operations attributable to noncontrolling interests ​ ​ ( 179,089 ) ​ ​ ( 5,620 ) ​ ​ ( 11,251 ) Net income (loss) allocable to common shareholders ​ $ 397,792 ​ $ 108,985 ​ $ ( 65,937 ) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Denominator for basic and diluted earnings per share: ​ ​ ​ Weighted average common shares outstanding for basic and diluted earnings per common share ​ 80,722 ​ 71,831 ​ 75,684 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Basic and diluted earnings per common share: (1) ​ ​ ​ Net loss from continuing operations and allocable to common shareholders ​ $ ( 2.74 ) ​ $ ( 0.10 ) ​ $ ( 1.85 ) Net income from discontinued operations and allocable to common shareholders ​ ​ 7.66 ​ ​ 1.61 ​ ​ 0.98 Net income (loss) allocable to common shareholders ​ $ 4.92 ​ $ 1.51 ​ $ ( 0.87 ) (1) For the year ended December 31, 2022, 2021 and 2020, the effect of certain of the Company’s restricted stock awards were anti-dilutive due to the Company having a net loss from continuing operations and allocable to common shareholders for the period. For the years ended December 31, 2022 and 2021, 2,737,451 and 6,441,572 shares, respectively, of the 3.125 % Convertible Notes were anti-dilutive due to the Company having a net loss from continuing operations and allocable to common shareholders for the period. For the year ended December 31, 2020, no shares of common stock would have been issuable upon conversion of the 3.125 % Convertible Notes, and therefore the 3.125 % Convertible Notes had no effect on diluted EPS for such period . Note 16—Fair Values Fair value represents the price that would be received to sell an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date. The following fair value hierarchy prioritizes the inputs to be used in valuation techniques to measure fair value: Level 1: Unadjusted quoted prices in active markets that are accessible at the measurement date for identical, unrestricted assets or liabilities; Level 2: Quoted prices in markets that are not active, or inputs which are observable, either directly or indirectly, for substantially the full term of the asset or liability; and 88 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Level 3: Prices or valuation techniques that require inputs that are both significant to the fair value measurement and unobservable (i.e., supported by little or no market activity). Certain of the Company’s assets and liabilities are recorded at fair value either on a recurring or non-recurring basis. Assets required to be marked-to-market and reported at fair value every reporting period are classified as being valued on a recurring basis. Assets not required to be recorded at fair value every period may be recorded at fair value if a specific provision or other impairment is recorded within the period to mark the carrying value of the asset to market as of the reporting date. Such assets are classified as being valued on a non-recurring basis. The following fair value hierarchy table summarizes the Company’s assets and liabilities recorded at fair value on a recurring and non-recurring basis by the above categories ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Fair Value Using ​ ​ ​ ​ ​ Quoted ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ market ​ Significant ​ ​ ​ ​ ​ ​ ​ ​ prices in ​ other ​ Significant ​ ​ ​ ​ ​ active ​ observable ​ unobservable ​ ​ ​ ​ ​ markets ​ inputs ​ inputs ​ Total (Level 1) (Level 2) (Level 3) As of December 31, 2022 ​ ​ ​ ​ ​ ​ ​ ​ Non-recurring basis: ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Real estate, net (1) ​ $ 811 ​ $ — ​ $ — ​ $ 811 Impaired land and development (2) ​ ​ 26,300 ​ ​ — ​ ​ — ​ ​ 26,300 Loans receivable held for sale (refer to Note 7) ​ 37,650 ​ — ​ — ​ 37,650 As of December 31, 2021 ​ ​ ​ ​ Recurring basis: ​ ​ ​ ​ Derivative liabilities (3) ​ $ 8,395 ​ $ — $ 8,395 $ — Available-for-sale securities (3) ​ ​ 28,092 ​ ​ — ​ ​ — ​ ​ 28,092 (1) The Company recorded a $ 1.8 million impairment on an operating property with an estimated fair value of $ 0.8 million. The estimated fair value is based on the cash flows expected to be received. (2) The Company recorded a $ 12.7 million on a land and development asset with an estimated fair value of $ 26.3 million. The estimated fair value is based on future cash flows expected to be received using a discount rate of 12.5 % . (3) The fair value of the Company’s derivatives are based upon widely accepted valuation techniques utilized by a third-party specialist using observable inputs such as interest rates and contractual cash flow and are classified as Level 2. The fair value of the Company’s available-for-sale securities are based upon unadjusted third-party broker quotes and are classified as Level 3. As of December 31, 2021, derivative liabilities are recorded in “Liabilities associated with real estate held for sale and classified as discontinued operations” on the Company’s consolidated balance sheet. ​ The following table summarizes changes in Level 3 available-for-sale securities reported at fair value on the Company’s consolidated balance sheets for the years ended December 31, 2022 and 2021 ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ 2022 2021 Beginning balance ​ $ 28,092 ​ $ 25,274 Purchases ​ ​ — ​ ​ 3,375 Sales and Repayments ​ ( 26,752 ) ​ ( 200 ) Realized gain recorded in other income ​ ​ 2,897 ​ ​ — Unrealized losses recorded in other comprehensive income ​ ( 4,237 ) ​ ( 357 ) Ending balance ​ $ — ​ $ 28,092 ​ 89 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Fair values of financial instruments— The following table presents the carrying value and fair value for the Company’s financial instruments ($ in millions): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ As of December 31, 2022 ​ As of December 31, 2021 ​ ​ Carrying ​ Fair ​ Carrying ​ Fair ​ Value Value Value Value Assets ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Net investment in leases (refer to Note 5) (1) ​ $ — ​ $ — ​ $ 43 ​ $ 43 Loans receivable and other lending investments, net (1) ​ ​ 49 ​ ​ 46 ​ ​ 333 ​ ​ 345 Loans receivable held for sale (1) ​ ​ 38 ​ ​ 38 ​ ​ 43 ​ ​ 43 Cash and cash equivalents (2) ​ 1,442 ​ 1,442 ​ 340 ​ 340 Restricted cash (2) ​ 6 ​ 6 ​ 54 ​ 54 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Liabilities ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Debt obligations, net (1)(3) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Level 1 ​ ​ 1,584 ​ ​ 1,588 ​ ​ 2,473 ​ ​ 2,799 Level 3 ​ ​ 99 ​ ​ 98 ​ ​ 99 ​ ​ 104 Total debt obligations, net ​ ​ 1,683 ​ ​ 1,686 ​ ​ 2,572 ​ ​ 2,903 (1) The fair value of the Company’s net investment in leases, loans receivable and other lending investments, net, loans receivable held for sale and certain debt obligations, net are classified as Level 3 within the fair value hierarchy. (2) The Company determined the carrying values of its cash and cash equivalents and restricted cash approximated their fair values. Restricted cash is recorded in “Deferred expenses and other assets, net” on the Company’s balance sheet. The fair value of the Company’s cash and cash equivalents and restricted cash are classified as Level 1 within the fair value hierarchy. (3) As of December 31, 2022 and 2021, the fair value of the Company’s unsecured notes and Senior Term Loan are classified as Level 1 within the fair value hierarchy. As of December 31, 2021, the fair value of the Company’s 3.125 % Senior Convertible Notes was $ 527.5 million. Derivatives —The Company may use interest rate swaps, interest rate caps and foreign exchange contracts to manage its interest rate and foreign currency risk. The valuation of these instruments is determined using discounted cash flow analysis on the expected cash flows of each derivative. This analysis reflects the contractual terms of the derivatives, including the period to maturity, and uses observable market-based inputs, including interest rate curves, foreign exchange rates, and implied volatilities. The Company incorporates credit valuation adjustments to appropriately reflect both its own non-performance risk and the respective counterparty’s non-performance risk in the fair value measurements. In adjusting the fair value of its derivative contracts for the effect of non-performance risk, the Company has considered the impact of netting and any applicable credit enhancements, such as collateral postings, thresholds, mutual puts and guarantees. The Company has determined that the significant inputs used to value its derivatives fall within Level 2 of the fair value hierarchy. Impaired real estate — The Company reviews real estate assets to be held for use and land and development assets for impairment in value whenever events or changes in circumstances indicate that the carrying amount of such assets may not be recoverable. The value of a long-lived asset held for use and land and development assets are impaired only if management’s estimate of the aggregate future cash flows (undiscounted and without interest charges) to be generated by the asset (taking into account the anticipated holding period of the asset) is less than the carrying value. Such estimate of cash flows considers factors such as expected future operating income trends, as well as the effects of demand, competition and other economic factors. If the Company determines a real estate asset available and held for sale is impaired, it records an impairment charge to adjust the asset to its estimated fair market value less costs to sell. Due to the nature of individual real estate properties, the Company generally uses a discounted cash flow methodology through internally developed valuation models to estimate the fair value of the assets. This approach requires the Company to make judgments with respect to significant unobservable inputs, which may include discount rates, capitalization rates and the timing and amounts of estimated future cash flows. For income producing properties, cash flows generally include property revenues, operating costs and capital expenditures that are based on current observable market rates and estimates for market rate growth and occupancy levels. For other real estate, cash flows may include lot and unit sales that are based on current observable market rates and estimates for annual market rate growth, operating costs, costs of completion and the inventory sell out pricing and timing. The Company will also consider comparable market transactions, if available. In some cases, the 90 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Company obtains external “as is” appraisals for real estate assets and appraised values may be discounted when real estate markets rapidly deteriorate. The Company has determined that significant inputs used in its internal valuation models and appraisals fall within Level 3 of the fair value hierarchy. Additionally, in certain cases, if the Company is under contract to sell an asset, it will mark the asset to the contracted sales price less costs to sell. The Company considers this to be a Level 3 input under the fair value hierarchy. Loans receivable and other lending investments, net —The Company estimates the fair value of its performing loans and other lending investments using a discounted cash flow methodology. This method discounts estimated future cash flows using rates management determines best reflect current market interest rates that would be offered for loans with similar characteristics and credit quality. The Company determined that the significant inputs used to value its loans and other lending investments fall within Level 3 of the fair value hierarchy. For certain lending investments, the Company uses market quotes, to the extent they are available, that fall within Level 2 of the fair value hierarchy or broker quotes that fall within Level 3 of the fair value hierarchy. The Company estimates the fair value of its non-performing loans using a discounted cash flow methodology through internally developed valuation models to estimate the fair value of the collateral. This approach requires the Company to make judgments in respect to significant unobservable inputs, which may include discount rates, capitalization rates and the timing and amounts of estimated future cash flows. For income producing properties, cash flows generally include property revenues, operating costs and capital expenditures that are based on current observable market rates and estimates for market rate growth and occupancy levels. For other real estate, cash flows may include lot and unit sales that are based on current observable market rates and estimates for annual revenue growth, operating costs, costs of completion and the inventory sell out pricing and timing. The Company will also consider comparable market transactions, if available. In some cases, the Company obtains external “as is” appraisals for loan collateral, generally when third party participations exist, and appraised values may be discounted when real estate markets rapidly deteriorate. The Company has determined that significant inputs used in its internal valuation models and appraisals fall within Level 3 of the fair value hierarchy. Debt obligations, net —For debt obligations traded in secondary markets, the Company uses market quotes, to the extent they are available, to determine fair value and are considered Level 2 on the fair value hierarchy. For debt obligations not traded in secondary markets, the Company determines fair value using a discounted cash flow methodology, whereby contractual cash flows are discounted at rates that management determines best reflect current market interest rates that would be charged for debt with similar characteristics and credit quality. The Company has determined that the inputs used to value its debt obligations under the discounted cash flow methodology fall within Level 3 of the fair value hierarchy. Note 17—Segment Reporting The Company has determined that it has four reportable segments based on how management reviews and manages its business. These reportable segments include: Net Lease, Real Estate Finance, Operating Properties and Land and Development. The Net Lease segment (Refer to Note 3 - Net Lease Sale and Discontinued Operations) includes the Company’s investments in SAFE and its Ground Lease adjacent businesses (refer to Note 8). The Real Estate Finance segment includes all of the Company’s activities related to senior and mezzanine real estate loans and real estate related securities. The Operating Properties segment includes the Company’s activities and operations related to its commercial and residential properties. The Land and Development segment includes the Company’s activities related to its developable land portfolio. ​ 91 Table of Contents iStar Inc. Notes to Consolidated Financial Statements The Company evaluates performance based on the following financial measures for each segment. The Company’s segment information is as follows ($ in thousands): 92 Table of Contents iStar Inc. Notes to Consolidated Financial Statements ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Net Real Estate Operating Land and Corporate/ Company ​ ​ Lease (1) ​ Finance ​ Properties ​ Development ​ Other (2) ​ Total Year Ended December 31, 2022 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Operating lease income ​ $ — ​ $ — ​ $ 12,454 ​ $ 405 ​ $ — ​ $ 12,859 Interest income ​ 75 ​ 12,340 ​ — ​ — ​ — ​ 12,415 Interest income from sales-type leases ​ 861 ​ — ​ 8 ​ — ​ — ​ 869 Other income ​ 20,560 ​ 3,570 ​ 27,188 ​ 6,323 ​ 12,514 ​ 70,155 Land development revenue ​ — ​ — ​ — ​ 61,753 ​ — ​ 61,753 Earnings (losses) from equity method investments ​ 41,692 ​ 4,623 ​ 14,850 ​ 4,775 ​ ( 7,260 ) ​ 58,680 Income from sales of real estate ​ 1,443 ​ — ​ 25,186 ​ — ​ — ​ 26,629 Total revenue and other earnings ​ 64,631 ​ 20,533 ​ 79,686 ​ 73,256 ​ 5,254 ​ 243,360 Real estate expense ​ ( 1,387 ) ​ ​ — ​ ( 33,900 ) ​ ( 16,327 ) ​ — ​ ( 51,614 ) Land development cost of sales ​ — ​ — ​ — ​ ( 63,441 ) ​ — ​ ( 63,441 ) Other expense ​ ( 595 ) ​ ( 308 ) ​ — ​ ( 498 ) ​ ( 7,512 ) ​ ( 8,913 ) Allocated interest expense ​ ( 54,781 ) ​ ( 8,306 ) ​ ( 4,649 ) ​ ( 10,865 ) ​ ( 19,450 ) ​ ( 98,051 ) Allocated general and administrative (3) ​ ( 15,596 ) ​ ( 4,044 ) ​ ( 2,255 ) ​ ( 8,197 ) ​ ( 18,843 ) ​ ( 48,935 ) Segment profit (loss) (4) ​ $ ( 7,728 ) ​ $ 7,875 ​ $ 38,882 ​ $ ( 26,072 ) ​ $ ( 40,551 ) ​ $ ( 27,594 ) Other significant items: ​ ​ ​ ​ ​ ​ Provision for loan losses ​ $ — ​ $ 44,998 ​ $ — ​ $ — ​ $ — ​ $ 44,998 Impairment of assets ​ — ​ — ​ 2,364 ​ 12,727 ​ 18 ​ 15,109 Depreciation and amortization ​ — ​ — ​ 3,797 ​ 1,113 ​ 560 ​ 5,470 Capitalized expenditures ​ — ​ — ​ 881 ​ 20,518 ​ — ​ 21,399 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Year Ended December 31, 2021 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Operating lease income ​ $ — ​ $ — ​ $ 16,445 ​ $ 379 ​ $ — ​ $ 16,824 Interest income ​ ​ 1,707 ​ 29,522 ​ — ​ — ​ — ​ 31,229 Interest income from sales-type leases ​ ​ 1,215 ​ — ​ — ​ — ​ — ​ 1,215 Other income ​ ​ 14,888 ​ 1,260 ​ 27,342 ​ 6,899 ​ 19,870 ​ 70,259 Land development revenue ​ ​ — ​ — ​ — ​ 189,103 ​ — ​ 189,103 Earnings (losses) from equity method investments ​ ​ 108,399 ​ 3,074 ​ 15,108 ​ 21,492 ​ 6,271 ​ 154,344 Income from sales of real estate ​ — ​ — ​ 26,319 ​ — ​ — ​ 26,319 Total revenue and other earnings ​ 126,209 ​ 33,856 ​ 85,214 ​ 217,873 ​ 26,141 ​ 489,293 Real estate expense ​ ( 424 ) ​ ​ — ​ ( 27,020 ) ​ ( 18,550 ) ​ — ​ ( 45,994 ) Land development cost of sales ​ — ​ — ​ — ​ ( 171,961 ) ​ — ​ ( 171,961 ) Other expense ​ ( 587 ) ​ ( 515 ) ​ — ​ ( 70 ) ​ ( 6,942 ) ​ ( 8,114 ) Allocated interest expense ​ ( 61,685 ) ​ ( 14,830 ) ​ ( 6,949 ) ​ ( 15,242 ) ​ ( 16,694 ) ​ ( 115,400 ) Allocated general and administrative (3) ​ ( 25,077 ) ​ ( 4,736 ) ​ ( 2,227 ) ​ ( 9,555 ) ​ ( 20,847 ) ​ ( 62,442 ) Segment profit (loss) (4) ​ $ 38,436 ​ $ 13,775 ​ $ 49,018 ​ $ 2,495 ​ $ ( 18,342 ) ​ $ 85,382 Other significant items: ​ ​ ​ ​ ​ ​ Provision for loan losses ​ $ — ​ $ ( 8,085 ) ​ $ — ​ $ — ​ $ — ​ $ ( 8,085 ) Impairment of assets ​ — ​ — ​ 678 ​ — ​ — ​ 678 Depreciation and amortization ​ — ​ — ​ 5,585 ​ 902 ​ 585 ​ ​ 7,072 Capitalized expenditures ​ 2,578 ​ — ​ 655 ​ 24,036 ​ — ​ 27,269 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Year Ended December 31, 2020 ​ ​ ​ ​ ​ ​ Operating lease income ​ $ 2,706 ​ $ — ​ $ 21,214 ​ $ 356 ​ $ — ​ $ 24,276 Interest income ​ — ​ 56,676 ​ — ​ — ​ — ​ 56,676 Other income ​ 12,704 ​ 11,975 ​ 8,065 ​ 19,030 ​ 26,671 ​ 78,445 Land development revenue ​ — ​ — ​ — ​ 164,702 ​ — ​ 164,702 Earnings (losses) from equity method investments ​ 53,476 ​ — ​ ( 16,361 ) ​ 3,432 ​ ( 1,075 ) ​ 39,472 Income from sales of real estate ​ 6,056 ​ — ​ 262 ​ — ​ — ​ 6,318 Total revenue and other earnings ​ 74,942 ​ 68,651 ​ 13,180 ​ 187,520 ​ 25,596 ​ 369,889 Real estate expense ​ ( 161 ) ​ — ​ ( 22,936 ) ​ ( 22,986 ) ​ — ​ ( 46,083 ) Land development cost of sales ​ — ​ — ​ — ​ ( 177,727 ) ​ — ​ ( 177,727 ) Other expense ​ — ​ ( 266 ) ​ — ​ — ​ ( 303 ) ​ ( 569 ) Allocated interest expense ​ ( 58,462 ) ​ ( 23,390 ) ​ ( 8,951 ) ​ ( 17,940 ) ​ ( 18,085 ) ​ ( 126,828 ) Allocated general and administrative (5) ​ ( 23,223 ) ​ ( 6,622 ) ​ ( 2,591 ) ​ ( 9,990 ) ​ ( 19,099 ) ​ ( 61,525 ) Segment profit (loss) (4) ​ $ ( 6,904 ) ​ $ 38,373 ​ $ ( 21,298 ) ​ $ ( 41,123 ) ​ $ ( 11,891 ) ​ $ ( 42,843 ) Other significant non-cash items: ​ ​ ​ ​ ​ ​ Provision for loan losses ​ $ — ​ $ 8,866 ​ $ — ​ $ — ​ $ — ​ $ 8,866 Impairment of assets ​ — ​ — ​ 3,053 ​ 2,738 ​ — ​ 5,791 Depreciation and amortization ​ — ​ ​ — ​ ​ 5,142 ​ ​ 952 ​ ​ 1,233 ​ 7,327 Capitalized expenditures ​ 21,764 ​ — ​ 1,636 ​ 30,506 ​ — ​ 53,906 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ 93 Table of Contents iStar Inc. Notes to Consolidated Financial Statements As of December 31, 2022 ​ ​ ​ ​ ​ ​ Real estate, net ​ $ — ​ $ — ​ $ 76,497 ​ $ — ​ $ — ​ $ 76,497 Real estate available and held for sale ​ — ​ — ​ 3,977 ​ — ​ — ​ 3,977 Total real estate ​ — ​ — ​ 80,474 ​ — ​ — ​ 80,474 Real estate and other assets available and held for sale and classified as discontinued operations (1) ​ ​ 2,939 ​ ​ — ​ ​ — ​ ​ — ​ ​ — ​ ​ 2,939 Land and development, net ​ — ​ — ​ — ​ 232,014 ​ — ​ 232,014 Loans receivable and other lending investments, net ​ — ​ 48,655 ​ — ​ — ​ — ​ 48,655 Loan receivable held for sale ​ — ​ 37,650 ​ — ​ — ​ — ​ 37,650 Other investments ​ ​ 1,302,877 ​ ​ 25,389 ​ ​ 32,405 ​ ​ — ​ ​ 11 ​ ​ 1,360,682 Total portfolio assets ​ $ 1,305,816 ​ $ 111,694 ​ $ 112,879 ​ $ 232,014 ​ $ 11 ​ 1,762,414 Cash and other assets ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ 1,490,814 Total assets ​ ​ ​ ​ ​ ​ ​ ​ $ 3,253,228 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ As of December 31, 2021 ​ ​ ​ ​ ​ ​ Real estate, net ​ $ — ​ $ — ​ $ 92,150 ​ $ — ​ $ — ​ $ 92,150 Real estate available and held for sale ​ — ​ — ​ 301 ​ — ​ — ​ 301 Total real estate ​ — ​ — ​ 92,451 ​ — ​ — ​ 92,451 Real estate and other assets available and held for sale and classified as discontinued operations (1) ​ ​ 2,299,711 ​ ​ — ​ ​ — ​ ​ — ​ ​ — ​ ​ 2,299,711 Net investment in leases ​ 43,215 ​ — ​ — ​ — ​ — ​ 43,215 Land and development, net ​ — ​ — ​ — ​ 286,810 ​ — ​ 286,810 Loans receivable and other lending investments, net ​ — ​ 332,844 ​ — ​ — ​ — ​ 332,844 Loan receivable held for sale ​ ​ 43,215 ​ — ​ — ​ — ​ — ​ ​ 43,215 Other investments ​ 1,186,162 ​ ​ 48,862 ​ ​ 43,252 ​ ​ 1,096 ​ ​ 17,909 ​ 1,297,281 Total portfolio assets ​ $ 3,572,303 ​ $ 381,706 ​ $ 135,703 ​ $ 287,906 ​ $ 17,909 ​ 4,395,527 Cash and other assets ​ ​ ​ ​ ​ ​ ​ ​ 445,007 Total assets ​ ​ ​ ​ ​ ​ ​ ​ $ 4,840,534 (1) Refer to Note 3 – Net Lease Sale and Discontinued Operations. (2) Corporate/Other represents all corporate level and unallocated items including any intercompany eliminations necessary to reconcile to consolidated Company totals. This caption also includes the Company’s joint venture investments and strategic investments that are not included in the other reportable segments above. (3) General and administrative excludes stock-based compensation of ($ 27.7 ) million, $ 69.3 million and $ 39.4 million for the years ended December 31, 2022, 2021 and 2020, respectively. (4) The following is a reconciliation of segment profit to net income (loss) ($ in thousands): ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ For the Years Ended December 31, ​ ​ 2022 2021 2020 Segment profit ​ $ ( 27,594 ) ​ $ 85,382 ​ $ ( 42,843 ) Less: (Provision for) recovery of loan losses ​ ( 44,998 ) ​ 8,085 ​ ( 8,866 ) Less: Impairment of assets ​ ( 15,109 ) ​ ( 678 ) ​ ( 5,791 ) Less: Stock-based compensation ​ 27,664 ​ ( 69,261 ) ​ ( 39,354 ) Less: Depreciation and amortization ​ ( 5,470 ) ​ ( 7,072 ) ​ ( 7,327 ) Less: Income tax benefit (expense) ​ ( 567 ) ​ 118 ​ ( 89 ) Less: Loss on early extinguishment of debt, net ​ ( 131,200 ) ​ — ​ ( 12,038 ) Less: Net income from discontinued operations ​ ​ 797,688 ​ ​ 121,452 ​ ​ 85,455 Net income (loss) ​ $ 600,414 ​ $ 138,026 ​ $ ( 30,853 ) ​ ​ ​ ​ 94 Table of Contents iStar Inc. Notes to Consolidated Financial Statements Note 18 — Selected Quarterly Financial Data (unaudited) ​ The following table sets forth the selected quarterly financial data (unaudited) for the Company ($ in thousands, except per share amounts). Certain amounts have been reclassified from the prior period presentation (Refer to Note 3 - Net Lease Sale and Discontinued Operations). ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ For the Quarters Ended ​ December 31, September 30, June 30, March 31, 2022 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Revenue ​ $ 30,278 ​ $ 47,757 ​ $ 48,063 ​ $ 31,953 Net income (loss) from continuing operations ​ ( 80,844 ) ​ 17,952 ​ ( 132,494 ) ​ ( 1,888 ) Net income from discontinued operations ​ — ​ — ​ — ​ 797,688 Net income (loss) allocable to common shareholders ​ ​ ( 86,709 ) ​ ​ 12,131 ​ ​ ( 138,485 ) ​ ​ 610,855 Earnings per share (1) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Net income (loss) from continuing operations ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Basic ​ $ ( 1.00 ) ​ $ 0.14 ​ $ ( 1.70 ) ​ $ ( 0.11 ) Diluted ​ ​ ( 1.00 ) ​ ​ 0.14 ​ ​ ( 1.70 ) ​ ​ ( 0.11 ) Net income from discontinued operations ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Basic ​ $ — ​ $ — ​ $ — ​ $ 8.96 Diluted ​ ​ — ​ ​ — ​ ​ — ​ ​ 8.96 Net income (loss) allocable to common shareholders ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Basic ​ $ ( 1.00 ) ​ $ 0.14 ​ $ ( 1.70 ) ​ $ 8.85 Diluted ​ ​ ( 1.00 ) ​ ​ 0.14 ​ ​ ( 1.70 ) ​ ​ 8.85 Weighted average number of common shares ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Basic ​ ​ 86,704 ​ ​ 85,458 ​ ​ 81,442 ​ ​ 69,037 Diluted ​ ​ 86,704 ​ ​ 85,687 ​ ​ 81,442 ​ ​ 69,037 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ 2021 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Revenue ​ $ 50,760 ​ $ 143,632 ​ $ 54,254 ​ $ 59,984 Net income (loss) from continuing operations ​ ( 41,578 ) ​ 109,380 ​ ( 36,731 ) ​ ( 14,497 ) Net income from discontinued operations ​ 52,037 ​ 21,614 ​ 25,315 ​ 22,486 Net income (loss) allocable to common shareholders ​ ​ 7,077 ​ ​ 121,856 ​ ​ ( 19,543 ) ​ ​ ( 405 ) Earnings per share (1) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Net income (loss) from continuing operations ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Basic ​ $ ( 0.68 ) ​ $ 1.45 ​ $ ( 0.59 ) ​ $ ( 0.28 ) Diluted ​ ​ ( 0.68 ) ​ ​ 1.28 ​ ​ ( 0.59 ) ​ ​ ( 0.28 ) Net income from discontinued operations ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Basic ​ $ 0.79 ​ $ 0.26 ​ $ 0.32 ​ $ 0.27 Diluted ​ ​ 0.79 ​ ​ 0.23 ​ ​ 0.32 ​ ​ 0.27 Net income (loss) allocable to common shareholders ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Basic ​ $ 0.11 ​ $ 1.71 ​ $ ( 0.27 ) ​ $ ( 0.01 ) Diluted ​ ​ 0.11 ​ ​ 1.51 ​ ​ ( 0.27 ) ​ ​ ( 0.01 ) Weighted average number of common shares ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Basic ​ ​ 69,328 ​ ​ 71,299 ​ ​ 72,872 ​ ​ 73,901 Diluted ​ ​ 69,328 ​ ​ 80,487 ​ ​ 72,872 ​ ​ 73,901 (1) Basic and diluted EPS are computed independently based on the weighted-average shares of common stock and stock equivalents outstanding for each period. Accordingly, the sum of the quarterly EPS amounts may not agree to the total for the year. ​ ​ ​ ​ ​ 95 Table of Contents iStar Inc. Schedule II—Valuation and Qualifying Accounts and Reserves ($ in thousands) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Balance at ​ Charged to ​ Adjustments ​ ​ ​ ​ Balance at ​ ​ Beginning ​ Costs and ​ to Valuation ​ ​ ​ ​ End ​ of Period Expenses Accounts Deductions of Period For the Year Ended December 31, 2020 ​ ​ ​ ​ ​ Continuing Operations ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Reserve for loan losses (1)(2) ​ $ 28,634 ​ $ 8,866 ​ $ 409 ​ $ ( 25,889 ) ​ $ 12,020 Allowance for doubtful accounts (2) ​ 731 ​ 1,324 ​ — ​ ( 896 ) ​ 1,159 Allowance for deferred tax assets (2) ​ 79,645 ​ 456 ​ — ​ — ​ 80,101 ​ ​ $ 109,010 ​ $ 10,646 ​ $ 409 ​ $ ( 26,785 ) ​ $ 93,280 Discontinued Operations ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Reserve for loan losses (1)(2) ​ $ — ​ $ 186 ​ $ 964 ​ $ — ​ $ 1,150 Reserve for losses on net investment in leases ​ ​ — ​ ​ 1,760 ​ ​ 9,111 ​ ​ — ​ ​ 10,871 Allowance for doubtful accounts (2) ​ ​ 1,211 ​ ​ ( 488 ) ​ ​ — ​ ​ ( 204 ) ​ ​ 519 ​ ​ $ 1,211 ​ $ 1,458 ​ $ 10,075 ​ $ ( 204 ) ​ $ 12,540 For the Year Ended December 31, 2021 ​ ​ ​ ​ ​ Continuing Operations ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Reserve for loan losses (1)(2) ​ $ 12,020 ​ $ ( 8,085 ) ​ $ 834 ​ $ — ​ $ 4,769 Allowance for doubtful accounts (2) ​ 1,159 ​ ( 907 ) ​ — ​ ( 198 ) ​ 54 Allowance for deferred tax assets (2) ​ 80,101 ​ ( 13,216 ) ​ 2,475 ​ — ​ 69,360 ​ ​ $ 93,280 ​ $ ( 22,208 ) ​ $ 3,309 ​ $ ( 198 ) ​ $ 74,183 Discontinued Operations ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Reserve for loan losses (1)(2) ​ $ 1,150 ​ $ ( 1,150 ) ​ $ — ​ $ — ​ $ — Reserve for losses on net investment in leases ​ ​ 10,871 ​ ​ ( 10,871 ) ​ ​ — ​ ​ — ​ ​ — Allowance for doubtful accounts (2) ​ ​ 519 ​ ​ 666 ​ ​ — ​ ​ ( 902 ) ​ ​ 283 ​ ​ $ 12,540 ​ $ ( 11,355 ) ​ $ — ​ $ ( 902 ) ​ $ 283 For the Year Ended December 31, 2022 ​ ​ ​ ​ ​ Continuing Operations ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Reserve for loan losses (1)(2) ​ $ 4,769 ​ $ 45,070 ​ $ — ​ $ ( 48,914 ) ​ $ 925 Allowance for doubtful accounts (2) ​ 54 ​ 189 ​ — ​ ( 161 ) ​ 82 Allowance for deferred tax assets (2) ​ 69,360 ​ ( 4,460 ) ​ — ​ — ​ 64,900 ​ ​ $ 74,183 ​ $ 40,799 ​ $ — ​ $ ( 49,075 ) ​ $ 65,907 Discontinued Operations ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Allowance for doubtful accounts (2) ​ $ 283 ​ $ ( 80 ) ​ $ — ​ $ ( 203 ) ​ $ — ​ ​ $ 283 ​ $ ( 80 ) ​ $ — ​ $ ( 203 ) ​ $ — (1) Refer to Note 7 to the Company’s consolidated financial statements. (2) Refer to Note 3 to the Company’s consolidated financial statements. ​ ​ ​ 96 Table of Contents iStar Inc. Schedule III—Real Estate and Accumulated Depreciation As of December 31, 2022 ($ in thousands) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Initial Cost to ​ Cost ​ Gross Amount Carried ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Company ​ Capitalized ​ at Close of Period ​ ​ ​ ​ ​ ​ Depreciable ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Building and ​ Subsequent to ​ ​ ​ ​ Building and ​ ​ ​ ​ Accumulated ​ Date ​ Life Location ​ ​ ​ Encumbrances ​ Land ​ Improvements ​ Acquisition (2) ​ Land ​ Improvements ​ Total ​ Depreciation ​ Acquired ​ (Years) LAND: ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ California LAN003 $ - ​ $ 28,464 $ 2,836 $ ( 19,453 ) $ 9,011 ​ $ 2,836 $ 11,847 $ 2,908 (3) 2010 ​ — New Jersey ​ LAN006 ​ - ​ 43,300 ​ - ​ 36,355 ​ 79,655 ​ - ​ 79,655 ​ 1,255 (3) 2009 ​ — New Jersey ​ LAN007 ​ - ​ 3,992 ​ - ​ 11,241 ​ 15,233 ​ - ​ 15,233 ​ - ​ 2009 ​ — New Jersey ​ LAN008 ​ - ​ 111 ​ 5,954 ​ 2,719 ​ 2,830 ​ 5,954 ​ 8,784 ​ - ​ 2009 ​ — New York ​ LAN009 ​ - ​ 58,900 ​ - ​ ( 32,600 ) ​ 26,300 ​ - ​ 26,300 ​ - ​ 2011 ​ — New York ​ LAN011 ​ - ​ 4,600 ​ - ​ - ​ 4,600 ​ - ​ 4,600 ​ - ​ 2018 ​ — Virginia ​ LAN012 ​ - ​ 72,138 ​ - ​ 25,170 ​ 97,308 ​ - ​ 97,308 ​ 7,550 (3) 2009 ​ — Subtotal ​ ​ ​ - ​ 211,505 ​ 8,790 ​ 23,432 ​ 234,937 ​ 8,790 ​ 243,727 ​ 11,713 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ RETAIL: ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Illinois ​ RET004 ​ $ - ​ $ - ​ $ 336 ​ $ 98 ​ $ - ​ $ 434 ​ $ 434 ​ $ 63 ​ 2010 ​ 40.0 Subtotal ​ ​ ​ - ​ - ​ 336 ​ 98 ​ - ​ 434 ​ 434 ​ 63 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ HOTEL: ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ New Jersey ​ HOT002 ​ $ - ​ $ 297 ​ $ 18,299 ​ $ 4,032 ​ $ 297 ​ $ 22,331 ​ $ 22,628 ​ $ 4,333 ​ 2019 ​ 40.0 New Jersey ​ HOT003 ​ - ​ 120 ​ 6,548 ​ 23 ​ 120 ​ 6,571 ​ 6,691 ​ 578 ​ 2019 ​ 40.0 New Jersey ​ HOT004 ​ - ​ 3,815 ​ 40,194 ​ 4,632 ​ 3,815 ​ 44,827 ​ 48,642 ​ 11,185 ​ 2016 ​ 40.0 Subtotal ​ ​ ​ - ​ 4,232 ​ 65,041 ​ 8,687 ​ 4,232 ​ 73,729 ​ 77,961 ​ 16,096 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ APARTMENT/RESIDENTIAL ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Virginia ​ APA005 ​ $ - ​ $ 264 ​ $ 616 ​ $ ( 76 ) ​ $ 264 ​ $ 540 ​ $ 804 ​ $ - ​ 2022 ​ 40.0 Virginia ​ APA006 ​ ​ - ​ ​ 267 ​ ​ 622 ​ ​ ( 133 ) ​ ​ 267 ​ ​ 489 ​ ​ 756 ​ ​ - ​ 2022 ​ 40.0 Virginia ​ APA007 ​ ​ - ​ ​ 267 ​ ​ 622 ​ ​ ( 133 ) ​ ​ 267 ​ ​ 489 ​ ​ 756 ​ ​ - ​ 2022 ​ 40.0 Virginia ​ APA008 ​ ​ - ​ ​ 266 ​ ​ 620 ​ ​ ( 132 ) ​ ​ 266 ​ ​ 487 ​ ​ 753 ​ ​ - ​ 2022 ​ 40.0 Virginia ​ APA009 ​ ​ - ​ ​ 147 ​ ​ 344 ​ ​ ( 73 ) ​ ​ 147 ​ ​ 271 ​ ​ 418 ​ ​ - ​ 2022 ​ 40.0 Virginia ​ APA010 ​ ​ - ​ ​ 147 ​ ​ 344 ​ ​ - ​ ​ 146 ​ ​ 344 ​ ​ 490 ​ ​ - ​ 2022 ​ 40.0 Subtotal ​ ​ ​ $ - ​ $ 1,358 ​ $ 3,168 ​ $ ( 547 ) ​ $ 1,357 ​ $ 2,620 ​ $ 3,977 ​ $ - ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ENTERTAINMENT: ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ New Jersey ​ ENT060 ​ $ - ​ $ 750 ​ $ 10,670 ​ $ 855 ​ $ 750 ​ $ 11,525 ​ $ 12,275 ​ $ 1,586 ​ 2017 ​ 40.0 New York ​ ENT063 ​ - ​ 3,277 ​ - ​ 646 ​ 587 ​ 3,336 ​ 3,923 ​ 350 ​ 2013 ​ 40.0 Subtotal ​ ​ ​ - ​ 4,027 ​ 10,670 ​ 1,501 ​ 1,337 ​ 14,861 ​ 16,198 ​ 1,936 ​ ​ ​ ​ TOTAL ​ ​ ​ $ - ​ $ 221,122 ​ $ 88,005 ​ $ 33,171 ​ $ 241,863 ​ $ 100,434 ​ $ 342,297 ​ $ 29,808 (4) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ (1) Includes impairments and unit sales. (2) These properties have land improvements which have depreciable lives of 15 to 20 years . (3) The aggregate cost for Federal income tax purposes was approximately $ 0.5 billion at December 31, 2022. (4) Includes $ 11.7 million relating to accumulated depreciation for land and development assets as of December 31, 2022. 97 Table of Contents iStar Inc. Schedule III—Real Estate and Accumulated Depreciation As of December 31, 2022 ($ in thousands) ​ The following table reconciles real estate, excluding real estate classified as discontinued operations, from January 1, 2020 to December 31, 2022: ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ 2022 2021 2020 Balance at January 1 ​ $ 415,963 ​ $ 660,896 ​ $ $ 817,382 Improvements and additions ​ 21,430 ​ 24,691 ​ 32,142 Acquisitions through foreclosure ​ — ​ — ​ - Other acquisitions ​ 5,213 ​ — ​ - Dispositions ​ ( 86,137 ) ​ ( 268,945 ) ​ ( 182,838 ) Impairments ​ ( 14,172 ) ​ ( 679 ) ​ ( 5,790 ) Balance at December 31 ​ $ 342,297 ​ $ 415,963 ​ $ 660,896 ​ The following table reconciles accumulated depreciation, excluding accumulated depreciation for real estate classified as discontinued operations, from January 1, 2020 to December 31, 2022: ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ 2022 2021 2020 Balance at January 1 ​ $ ( 36,702 ) ​ $ ( 32,643 ) ​ $ ( 28,049 ) Additions ​ ( 4,555 ) ​ ( 5,086 ) ​ ( 5,482 ) Dispositions ​ 11,449 ​ 1,027 ​ 888 Balance at December 31 ​ $ ( 29,808 ) ​ $ ( 36,702 ) ​ $ ( 32,643 ) ​ ​ 98 Table of Contents iStar Inc. Schedule III—Real Estate and Accumulated Depreciation As of December 31, 2022 ($ in thousands) ​ The following table reconciles real estate classified as discontinued operations from January 1, 2020 to December 31, 2022: ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ 2022 2021 2020 Balance at January 1 ​ $ 1,537,655 ​ $ 1,542,101 ​ $ 1,547,031 Improvements and additions ​ — ​ 2,578 ​ 21,764 Other acquisitions ​ — ​ 42,177 ​ — Dispositions ​ ( 1,537,443 ) ​ ( 23,201 ) ​ ( 26,694 ) Other ​ ( 212 ) ​ ( 26,000 ) ​ — Balance at December 31 ​ $ — ​ $ 1,537,655 ​ $ 1,542,101 ​ The following table reconciles accumulated depreciation classified as discontinued operations from January 1, 2020 to December 31, 2022: ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ 2022 2021 2020 Balance at January 1 ​ $ ( 271,183 ) ​ $ ( 250,198 ) ​ $ ( 219,949 ) Additions ​ — ​ ( 40,268 ) ​ ( 38,787 ) Dispositions ​ 271,183 ​ 8,224 ​ 8,538 Other ​ ​ — ​ ​ 11,059 ​ ​ — Balance at December 31 ​ $ — ​ $ ( 271,183 ) ​ $ ( 250,198 ) ​ ​ ​ ​ ​ ​ 99 Table of Contents iStar Inc. Schedule IV—Mortgage Loans on Real Estate As of December 31, 2022 ($ in thousands) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Contractual ​ Contractual ​ ​ ​ ​ ​ ​ ​ ​ Face ​ Carrying ​ ​ ​ ​ Interest ​ Interest ​ Effective ​ Periodic ​ ​ ​ ​ Amount ​ Amount ​ ​ ​ Accrual Payment Maturity Payment Prior of ​ of Type of Loan/Borrower Underlying Property Type Rates Rates Dates Terms (1) Liens Mortgages ​ Mortgages (2)(3) Senior Mortgages: ​ ​ ​ Borrower A Apartment/Residential LIBOR + 5.25 % LIBOR + 5.25 % June, 2023 IO ​ — ​ $ 6,765 ​ $ 6,756 Borrower B (4) Mixed Use/Mixed Collateral SOFR + 9.00 % SOFR + 9.00 % October, 2026 IO ​ — ​ 80,832 ​ 37,650 Borrower C Apartment/Residential LIBOR + 5.25 % LIBOR + 5.25 % December, 2022 IO ​ — ​ ​ 29,358 ​ ​ 29,097 ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ Subordinate Mortgages: ​ ​ ​ Borrower D ​ Hotel Fixed: 6.80 % Fixed: 6.80 % September, 2057 IO ​ — ​ 13,327 ​ 13,331 Total mortgages ​ ​ ​ ​ ​ $ 130,282 ​ $ 86,834 (1) IO = Interest only. (2) Amounts are presented net of asset-specific allowances of $ 0.4 million on impaired loans and loans held for sale. Impairment is measured using the estimated fair value of collateral, less costs to sell. (3) The carrying amount of mortgages approximated the federal income tax basis. (4) Classified as held for sale as of December 31, 2022. The Company has the intent to sell the loan based on a bid received from a third-party and the loan is recorded on the Company’s consolidated balance sheet at the estimated sales price. ​ 100 Table of Contents iStar Inc. Schedule IV—Mortgage Loans on Real Estate (Continued) As of December 31, 2022 ($ in thousands) ​ Reconciliation of Mortgage Loans on Real Estate: The following table reconciles Mortgage Loans on Real Estate from January 1, 2020 to December 31, 2022: (1) ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ 2022 2021 2020 Balance at January 1 ​ $ 211,488 ​ $ 496,553 ​ $ 561,761 Additions: ​ ​ ​ New mortgage loans ​ — ​ 32,942 ​ 19,975 Additions under existing mortgage loans ​ 6,482 ​ 20,958 ​ 72,574 Other (2) ​ 4,233 ​ 7,455 ​ 25,867 Deductions (3) : ​ ​ ​ Collections of principal ​ ( 111,112 ) ​ ( 304,053 ) ​ ( 178,662 ) Change in provision for loan losses ​ ( 24,237 ) ​ 166 ​ ( 4,930 ) Transfers to real estate and equity investments ​ — ​ ( 42,501 ) ​ — Amortization of premium ​ ( 20 ) ​ ( 32 ) ​ ( 32 ) Balance at December 31 ​ $ 86,834 ​ $ 211,488 ​ $ 496,553 (1) Balances represent the carrying value of loans, which are net of asset specific allowances. (2) Amount includes amortization of discount and deferred interest capitalized. (3) Amounts are presented net of charge-offs for the years ended December 31, 2022 and 2020. ​ ​ 101 Table of Contents Item 9. Changes and Disagreements with Registered Public Accounting Firm on Accounting and Financial Disclosure None.