What changed in this filing

/stocks — the workspaceLOADING

Item 8. Financial Statements and Supplementary Data

2024-03-01 compared with 2023-02-28 · 318 added, 308 removed, 1428 unchanged (30% of the section changed)

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Management's Report on Internal Control over Financial Reporting

Report of Independent Registered Public Accounting Firm (PCA O B ID:

Report of Independent Registered Public Accounting Firm (PCAOB ID:

Report of Independent Registered Public Accounting Firm

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In our opinion, the Company maintained, in all material respects, effective internal control over financial reporting as of December 31, 2023, 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 28, 2023, expressed an unqualified opinion on those financial statements.

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, 2023, of the Company and our report dated March 1, 2024, 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 Report on Internal Control over Financial Reporting.

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.

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New York, New York

February 28, 2023

March 1, 2024

REPORT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

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We have audited the accompanying consolidated balance sheets of Oppenheimer Holdings Inc.

and subsidiaries (the "Company") as of December 31, 2022 and 2021, the related consolidated statements of income, comprehensive income, changes in stockholders' equity and redeemable noncontrolling interests, and cash flows, for each of the three years in the period ended December 31, 2022, and the related notes (collectively referred to as the "financial statements").

and subsidiaries (the “Company”) as of December 31, 2023 and 2022, the related consolidated income statements, statements of comprehensive income, statements of changes in stockholders’ equity and redeemable noncontrolling interests, and statements of cash flows, for each of the three years in the period ended December 31, 2023, and the related notes (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, 2023 and 2022, and the results of its operations and its cash flows for each of the three years in the period ended December 31, 2023, 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 28, 2023, expressed an unqualified opinion on the Company's internal control over financial reporting.

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, 2023, 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 March 1, 2024, expressed an unqualified opinion on the Company’s internal control over financial reporting.

Basis for Opinion

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We believe that our audits provide a reasonable basis for our opinion.

Critical Audit Matters

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 matter 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.

Advisory Fees – Earned on Asset-based programs - Refer to Note 6 to the financial statements

Critical Audit Matter Description

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Fees are calculated based on underlying information, such as asset balances and rates, sourced from multiple internal and external systems.

For the year ended December 31, 2022, total advisory fee revenue was $426 million, of which $326 million represents fees earned on assets held in the Company’s asset-based programs.

Given the Company's use of multiple systems and databases in recording advisory fees on asset-based programs, auditing the balance was complex and challenging due to the extent of audit effort required to evaluate the completeness and accuracy of underlying information and required the involvement of information technology (IT) professionals with specialized skills and expertise.

Advisory fees earned on assets held in the Company’s asset-based programs are included as a part of the Company’s total advisory fee revenue.

Given the Company's use of multiple systems and databases in recording advisory fees earned on asset-based programs, auditing advisory fees earned on asset-based programs was complex and challenging due to the extent of audit effort required to

evaluate the completeness and accuracy of underlying information and required the involvement of information technology (IT) professionals with specialized skills and expertise.

How the Critical Audit Matter Was Addressed in the Audit

Our audit procedures related to the Company’s systems to process advisory revenue earned on asset-based programs included the following, among others:

• With the assistance of our IT specialists, we:

identified the significant systems used in the calculation of advisory fees and, using a risk-based approach, tested the relevant general IT controls over each of these systems.

Additionally, for

the relevant service organizations, we obtained the service auditor's reports and evaluated IT-related controls, related exceptions and complementary user entity controls specified in the reports.

• We tested the effectiveness of controls over the Company’s revenue balance, including automated business controls and system interface controls, as well as the controls designed to ensure the accuracy and completeness of advisory fee revenue.

• With the assistance of our data specialists, we created data visualizations to evaluate recorded advisory fee revenue and evaluate trends in the transactional revenue data.

• For a sample of revenue transactions, we performed detail transaction testing by agreeing the amounts recognized to source documents and testing the mathematical accuracy of the recorded advisory fee revenue.

• For a sample of accounts, we tested the accuracy and completeness of assets under management by obtaining independent pricing support and reconciling total positions to third-party statements.

Our audit procedures related to the Company’s systems to process advisory fees earned on asset-based programs included the following, among others:

• With the assistance of our IT specialists, we identified the significant systems used in the calculation of advisory fees earned on asset-based programs and, using a risk-based approach, tested the relevant general IT controls over each of these systems.

Additionally, for the relevant service organizations, we obtained the service auditor's reports and evaluated IT-related controls, related exceptions and complementary user entity controls specified in the reports.

• We tested the effectiveness of controls over the Company’s advisory fees earned on asset-based programs, including automated business controls and system interface controls, as well as the controls designed to ensure the accuracy and completeness of advisory fees earned on asset-based programs.

• With the assistance of our data specialists, we created data visualizations to evaluate recorded advisory fees earned on asset-based programs and evaluate trends in the transactional revenue data.

• For a sample of advisory fees earned on asset-based programs, we performed detail testing by agreeing the amounts recognized to source documents and testing the mathematical accuracy of the recorded advisory fees earned on asset-based programs.

• For a sample of accounts within the asset-based programs, we tested the accuracy and completeness of assets under management by obtaining independent pricing support and reconciling total positions to third-party statements.

/s/ Deloitte & Touche LLP

New York, New York

February 28, 2023

March 1, 2024

We have served as the Company's auditor since 2013.

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1,059,892 1,202,764

Income tax receivable 7,199 —

Securities purchased under agreements to resell 5,842 —

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LIABILITIES AND STOCKHOLDERS' EQUITY

Bank call loans — 69,500

Drafts payable $ 9,002 $ —

Payable to brokers, dealers and clearing organizations 361,890 550,006

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Commitments and contingencies (Note 18)

Redeemable noncontrolling interests 25,466 $ 127,765

Redeemable non-controlling interests — $ 25,466

Stockholders' equity

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Total Stockholders' Equity $ 789,239 $ 794,955

Total Liabilities, Redeemable Noncontrolling Interests and Stockholders' Equity $ 2,714,392 $ 3,043,250

(1) Certain prior period reported amounts were reclassified to conform to the current period presentation, See Note 2.

Total Liabilities, Redeemable Non-controlling Interests and Stockholders' Equity $ 2,874,816 $ 2,714,392

The accompanying notes are an integral part of these consolidated financial statements.

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Pre-tax income 46,770 45,554 224,641

Income taxes 13,444 65,677 46,014

Income tax provision 16,498 13,444 65,677

Net income $ 30,272 $ 32,110 $ 158,964

Net income (loss) attributable to noncontrolling interests, net of tax ( 241 ) — —

Net income (loss) attributable to non-controlling interests, net of tax 93 ( 241 ) —

Net income attributable to Oppenheimer Holdings Inc.

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Comprehensive income $ 29,770 $ 29,301 $ 159,741

Less net income (loss) attributable to noncontrolling interests ( 241 ) — —

Less net income (loss) attributable to non-controlling interests 93 ( 241 ) —

Comprehensive income attributable to Oppenheimer Holdings Inc.

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OPPENHEIMER HOLDINGS INC.

CONSOLIDATED STATEMENTS OF CHANGES IN STOCKHOLDERS' EQUITY AND REDEEMABLE NONCONTROLLING INTERESTS

CONSOLIDATED STATEMENTS OF CHANGES IN STOCKHOLDERS' EQUITY AND REDEEMABLE

NON-CONTROLLING INTERESTS

FOR THE THREE YEARS ENDED DECEMBER 31,

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Vested employee share plan awards ( 11,892 ) ( 5,081 ) ( 9,739 )

Change in redemption value of redeemable noncontrolling interests ( 221 ) ( 653 ) —

Change in redemption value of redeemable non-controlling interests ( 145 ) ( 221 ) ( 653 )

Balance at end of year 31,774 28,628 78,032

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Balance at beginning of year 722 2,069 11,946

Capital distribution to noncontrolling interests ( 90 ) — —

Net loss attributable to non-controlling interests ( 241 ) ( 11 ) —

Change in redemption value of redeemable noncontrolling interests ( 1,016 ) ( 9,866 ) —

Capital distribution to non-controlling interests ( 198 ) ( 90 ) —

Net income (loss) attributable to non-controlling interests 93 ( 241 ) ( 11 )

Change in redemption value of redeemable non-controlling interests ( 544 ) ( 1,016 ) ( 9,866 )

Balance at end of year 73 722 2,069

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Balance at beginning of year 25,466 127,765 117,246

Redemption of redeemable noncontrolling interests

Redemption of redeemable non-controlling interests

( 26,155 ) ( 103,536 ) —

Change in redemption value of redeemable noncontrolling interests 1,237 10,519 —

Change in redemption value of redeemable non-controlling interests 689 1,237 10,519

Balance at end of year $ — $ 25,466 $ 127,765

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Increase (decrease) in operating liabilities:

Drafts payable 9,002 — —

Payable to brokers, dealers and clearing organizations ( 188,116 ) 127,949 162,146

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Purchase of furniture, equipment and leasehold improvements ( 17,056 ) ( 16,311 ) ( 8,268 )

Acquisition of BondWave LLC, net of cash consideration ( 2,929 ) — —

Proceeds from the settlement of Company-owned life insurance 4,424 2,174 2,001

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Payments for employee taxes withheld related to vested share-based awards ( 5,907 ) ( 2,283 ) ( 4,967 )

Issuance of senior secured notes — 125,000

Payment of Company sponsored Initial Public Offering costs — — ( 454 )

Contributions from noncontrolling interests — 3,147 —

Contributions from non-controlling interests — — 3,147

Proceeds from Company sponsored Initial Public Offering — — 126,500

Distribution to noncontrolling interests ( 90 ) — —

Redemption on redeemable noncontrolling interests ( 103,536 ) — —

Redemption of senior secured notes — — ( 148,574 )

Distribution to non-controlling interests ( 198 ) ( 90 ) —

Redemption on redeemable non-controlling interests ( 26,155 ) ( 103,536 ) —

Repurchase of senior secured notes ( 1,000 ) ( 10,950 ) —

Debt issuance costs — — ( 22 )

Debt redemption costs — — ( 2,507 )

(Decrease)/increase in bank call loans, net ( 69,500 ) ( 12,500 ) 82,000

Decrease in bank call loans, net — ( 69,500 ) ( 12,500 )

Cash provided by/(used in) financing activities ( 74,761 ) ( 253,912 ) 84,581

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Employee share plan issuance $ 9,376 $ 4,288 $ 7,361

Fair value of non-cash assets acquired $ 6,658 $ — $ —

Fair value of liabilities assumed in acquisition $ 1,544 $ — $ —

Contingent consideration for BondWave LLC $ ( 1,395 ) $ — $ —

Supplemental disclosure of cash flow information

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Oppenheimer Holdings Inc., through its operating subsidiaries, is a leading middle market investment bank and full service broker-dealer that is engaged in a broad range of activities in the financial services industry, including retail securities brokerage, institutional sales and trading, investment banking (corporate and public finance), equity and fixed income research, market-making, trust services, and investment advisory and asset management services.

The Company is headquartered in New York and has 92 retail branch offices in the United States and institutional businesses located in London, Tel Aviv, and Hong Kong.

The Company is headquartered in New York and has 90 retail branch offices in 25 states located throughout the United States and offices in Puerto Rico, Tel Aviv, Israel, Hong Kong, China, London, England, St.

Helier, Isle of Jersey, Portugal and Geneva, Switzerland.

The principal subsidiaries of OPY are Oppenheimer & Co.

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Oppenheimer Trust Company of Delaware ("Oppenheimer Trust"), a limited purpose trust company that provides fiduciary services such as trust and estate administration and investment management;

OPY Credit Corp., which offers syndication as well as trading of issued corporate loans;

Oppenheimer Europe Ltd., based in the United Kingdom, with offices in the Isle of Jersey, Germany and Switzerland, which provides institutional equities and fixed income brokerage and corporate finance and is regulated by the Financial Conduct Authority in the United Kingdom and the Jersey Financial Services Commission in the Isle of Jersey;

OPY Credit Corp., which conducts secondary trading activities related to the purchase and sale of loans, primarily on a riskless principal basis;

Oppenheimer Europe Ltd., based in the United Kingdom, with offices in the Isle of Jersey, Portugal, and Switzerland, which provides institutional equities and fixed income brokerage and corporate finance and is regulated by the Financial Conduct Authority;

and Oppenheimer Investments Asia Limited, based in Hong Kong, China, which provides fixed income and equities brokerage services to institutional investors and is regulated by the Securities and Futures Commission.

and Oppenheimer Israel Ltd., based in Tel Aviv, Israel, which provides investment services in the State of Israel and operates subject to the authority of the Israel Securities Authority.

Oppenheimer owns Freedom Investments, Inc.

("Freedom"), a registered broker dealer in securities, which provides discount brokerage services, and Oppenheimer Israel (OPCO) Ltd., based in Tel Aviv, Israel, which provides investment services in the State of Israel and operates subject to the authority of the Israel Securities Authority.

Summary of significant accounting policies and estimates

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Change in Presentation

Effective June 30, 2022, the Company reclassified certain stockholders' equity amounts on the consolidated balance sheet and consolidated statements of changes in stockholders' equity and redeemable noncontrolling interests.

The reclassification included separately presenting the par value of common stock, and combining previously disclosed share capital and contributed capital amounts in the currently reported additional paid-in capital amount.

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Therefore, actual results could be materially different from these estimates.

Financial Instruments and F ai r Value

Financial Instruments

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Financial Instruments and F ai r Value

Financial Instruments

Securities owned, securities sold but not yet purchased, investments and derivative contracts are carried at fair value with changes in fair value recognized in earnings each period.

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Financial instruments classified within Level 1 are valued based on quoted market prices in active markets and consist of U.S.

Treasury, corporate equities, and certain money market instruments.

Treasury and corporate equities.

Level 2 financial instruments primarily consist of investment grade and high-yield corporate debt, convertible bonds, U.S.

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Some financial instruments are classified within Level 3 within the fair value hierarchy as observable pricing inputs are not available due to limited market activity for the asset or liability.

As of December 31, 2022 and December 31, 2021, the Company had $ 31.8 million of auction rate securities ("ARS") in level 3 assets.

As of December 31, 2023 and December 31, 2022, the Company had $ 2.7 million and $ 31.8 million respectively, of auction rate securities ("ARS") in Level 3 assets.

See note 8 for further details.

Fair Value Option

The Company elected the fair value option for securities sold under agreements to repurchase ("repurchase agreements") and securities purchased under agreements to resell ("reverse repurchase agreements") that do not settle overnight or have an open settlement date.

The Company has elected the fair value option for these instruments to reflect more accurately market and economic events in its earnings and to mitigate a potential mismatch in earnings caused by using different measurement attributes (i.e.

fair value versus carrying value) for certain assets and liabilities.

As of December 31, 2022, the Company did not have any repurchase agreements and reverse repurchase agreements that do not settle overnight or have an open settlement date.

Consolidation

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In many cases, the Company is permitted to sell or re-pledge securities held as collateral.

These securities may be used to collateralize repurchase

These securities may be used to collateralize repurchase agreements, to enter into securities lending agreements, to cover short positions or to fulfill the obligation of securities fails to deliver.

The Company monitors the fair value of the collateral received on a daily basis and may require clients and counterparties to deposit additional collateral or return collateral pledged, when appropriate.

Customer receivables, primarily consisting of customer margin loans collateralized by customer-owned securities, are stated net of allowance for credit losses.

The Company reviews large customer accounts that do not comply with the Company's margin

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

agreements, to enter into securities lending agreements, to cover short positions or to fulfill the obligation of securities fails to deliver.

The Company monitors the market value of the collateral received on a daily basis and may require clients and counterparties to deposit additional collateral or return collateral pledged, when appropriate.

Customer receivables, primarily consisting of customer margin loans collateralized by customer-owned securities, are stated net of allowance for credit losses.

The Company reviews large customer accounts that do not comply with the Company's margin requirements on a case-by-case basis to determine the likelihood of collection and records an allowance for credit loss following that process.

requirements on a case-by-case basis to determine the likelihood of collection and records an allowance for credit loss following that process.

For small customer accounts that do not comply with the Company's margin requirements, the allowance for credit loss is generally recorded as the amount of unsecured or partially secured receivables.

The Company also makes loans to financial advisors as part of its hiring process.

The Company also periodically makes loans to financial advisors and other revenue producers as part of its hiring process.

These loans are recorded as notes receivable on its consolidated balance sheet.

Allowances are established on these loans if the financial advisor is no longer associated with the Company and the loan has not been promptly repaid.

Allowances are established on these loans if the employee is no longer associated with the Company and the loan has not been promptly repaid.

Legal and Regulatory Reserves

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For these leases, lease expense is recognized on a straight-line basis over the lease term if the ROU asset has not been impaired or abandoned.

The Company defines a reporting unit as an operating segment.

The Company's goodwill resides in its Private Client Division ("PCD") reporting unit.

The Company's goodwill resides in its Private Client Division ("PCD") and Corporate/Other operating segment.

Goodwill of a reporting unit is subject to at least an annual test for impairment to determine if the estimated fair value of a reporting unit is less than its carrying amount.

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Due to the volatility in the financial services sector and equity markets in general, determining whether an impairment of goodwill has occurred is increasingly difficult and requires management to exercise significant judgment.

The Company's annual goodwill impairment analysis performed as of December 31, 2022 applied the same valuation methodologies with consistent inputs as that performed as of December 31, 2021.

Goodwill within the Corporate/Other operating segment relates to the Company’s acquisition of BondWave LLC, which closed on December 29, 2023.

Because the valuation of goodwill associated with this transaction was determined on the last business day of 2023, no impairment testing was deemed necessary.

The Company's annual goodwill impairment analysis performed over the goodwill within the PCD reporting unit as of December 31, 2023 applied the same valuation methodologies with consistent inputs as that performed as of December 31, 2022.

In estimating the fair value of the PCD reporting unit, the Company uses traditional standard valuation methods, including the market comparable approach and income approach.

The market comparable approach is based on comparisons of the subject

The market comparable approach is based on comparisons of the subject company to public companies whose stocks are actively traded ("Price Multiples") or to similar companies engaged in an actual

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

company to public companies whose stocks are actively traded ("Price Multiples") or to similar companies engaged in an actual merger or acquisition ("Precedent Transactions").

merger or acquisition ("Precedent Transactions").

As part of this process, multiples of value relative to financial variables, such as earnings or stockholders' equity, are developed and applied to the appropriate financial variables of the subject company to indicate its value.

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The fair value of the trademarks and trade names was substantially in excess of their carrying value as of December 31, 2023.

Defined-lived intangible assets are comprised of developed technology and customer relationships.

These intangible assets carried at $ 1.6 million are amortized over their estimated lives and are periodically evaluated for impairment whenever events or circumstances indicate that the carrying amount may not be recoverable from future undiscounted cash flows.

Share-Based Compensation Plans

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Realized and unrealized changes in fair value are recognized in principal transactions, net in the period in which the change occurs.

Investment Banking Fees

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Investment Banking Fees

Advisory fees from mergers, acquisitions and restructuring transactions are recorded when services for the transactions are completed and income is reasonably determinable, generally as set forth under the terms of the engagement.

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Interest revenue is recognized in the period earned based upon average or daily asset balances, contractual cash flows, and interest rates.

Interest earned from the customer margin loans is recorded in the consolidated income statements in interest income.

Asset Management

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Receivables from and payables to customers include balances arising from customer securities and margin transactions.

Receivables from customers are recorded when margin loans are extended to customers and are recorded on a settlement date basis.

Payables to customers are recorded when customers deposit cash into their accounts and are recorded on a settlement date basis.

Receivables from customers are recorded when margin loans are extended to customers and are recorded on a settlement date

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Payables to customers are recorded when customers deposit cash into their accounts and are recorded on a settlement date basis.

Securities Purchased under Agreements to Resell and Securities Sold under Agreements to Repurchase

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Additionally, the Company elected the fair value option for repurchase agreements and reverse repurchase agreements that do not settle overnight or have an open settlement date.

The Company can present the reverse repurchase and repurchase transactions on a net-by-counterparty basis when the specific offsetting requirements are satisfied.

The Company presents the reverse repurchase and repurchase transactions on a net-by-counterparty basis when the specific offsetting requirements are satisfied.

Notes Receivable

Notes receivable represent recruiting and retention payments generally in the form of upfront loans to financial advisors and key revenue producers as part of the Company's overall growth strategy.

Notes receivable primarily represent recruiting and retention payments generally in the form of upfront loans to financial advisors and key revenue producers as part of the Company's overall growth strategy.

These notes generally amortize over a service period of 3 to 10 years from the initial date of the note or based on productivity levels of employees.

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In making such a determination, the Company considers all available positive and negative evidence, including future reversals of existing taxable temporary differences, projected future taxable income, tax planning strategies, and the results of recent operations.

The Company records uncertain tax positions in accordance with Financial Accounting Standards Board ("FASB") Accounting Standards Codification ("ASC") 740, "Income Taxes", on the basis of a two-step process whereby it determines whether it is

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

more likely than not that the tax positions will be sustained on the basis of the technical merits of the position and for those tax positions that meet the more-likely-than-not recognition threshold, the Company recognizes the largest amount of tax benefit that is more than 50 percent likely to be realized upon ultimate settlement with the related tax authority.

The Company records uncertain tax positions on the basis of a two-step process whereby it determines whether it is more likely than not that the tax positions will be sustained on the basis of the technical merits of the position and for those tax positions that meet the more-likely-than-not recognition threshold, the Company recognizes the largest amount of tax benefit that is more than 50 percent likely to be realized upon ultimate settlement with the related tax authority.

The Company records interest and penalties accruing on unrecognized tax benefits in pre-tax income as interest expense and other expense, respectively, in its consolidated income statements.

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As a result, both OHAA and the Sponsor are recorded in the Company's consolidated financial statements.

Upon IPO completion, funds totaling $ 127.8 million, including proceeds from the OHAA IPO of $ 126.5 million and $ 1.3 million investment from the Sponsor, are held in a trust account until the earlier of (i) the completion of a Business Combination or (ii) ten business days after April 29, 2023, 18 months from the closing of the OHAA IPO (“Combination Period”), pursuant to OHAA's certificate of incorporation.

The cash held in the trust account is recorded in “Restricted Cash” on the consolidated balance sheet.

Transaction costs, which consisted of a net underwriting fee of $ 2.5 million and $ 0.5 million of other offering costs, were charged against the gross proceeds of the OHAA IPO consistent with SEC Staff Accounting Bulletin (SAB) Topic 5.

On December 20, 2022, OHAA’s stockholders approved an amendment to its certificate of incorporation that was filed with the Delaware Secretary of State on December 22, 2022 which extends the deadline by which it must complete its initial business combination from April 29, 2023 to October 30, 2023.

In connection with its proposal to amend its certificate of incorporation, OHAA was required to give its Class A stockholders the opportunity to redeem their shares of Class A common stock.

Of the 12,650,000 shares of Class A common stock that were outstanding, a total of 10,170,490 shares exercised their redemption rights.

As of December 31, 2022, $ 25.5 million remained in the trust account that is recorded within “Restricted Cash” on the consolidated balance sheet.

“Redeemable noncontrolling interests” of $ 25.5 million associated with the publicly held OHAA Class A ordinary shares are recorded on the Company’s consolidated balance sheet as of December 31, 2022 at redemption value and classified as temporary equity in accordance with Financial Accounting Standards Board (“FASB”) Accounting Standards Codification (“ASC”) Topic 480 “Distinguishing Liabilities from Equity”.

Changes in redemption value are recognized immediately as they occur and will adjust the carrying value of redeemable noncontrolling interests to equal the redemption value at the end of each reporting period.

Increases or decreases in the carrying amount of redeemable noncontrolling interests shall be affected by charges to additional paid-in-capital and noncontrolling interests attributable to certain members of the Sponsor on a pro rata ownership.

The public warrants and private warrants exercisable for OHAA Class A ordinary shares that were issued in connection with the OHAA IPO (the “OHAA Warrants”) qualify for equity accounting treatment under FASB ASC Topic 815.

Upon IPO completion, funds totaling $ 127.8 million, including proceeds from the OHAA IPO of $ 126.5 million and $ 1.3 million investment from the Sponsor, were held in a trust account until the earlier of (i) the completion of a Business Combination or (ii) ten business days after April 29, 2023, 18 months from the closing of the OHAA IPO (“Combination Period”), pursuant to OHAA's certificate of incorporation.

On October 26, 2023, OHAA’s stockholders approved an amendment to its certificate of incorporation to extend the deadline by which it must complete its initial business combination from October 30, 2023 to June 30, 2024 on a month-to-month basis.

However, a fter careful consideration of the current SPAC market and after having completed an extensive search, OHAA determined it would be unable to deliver and fund a high quality value enhancing transaction to stockholders despite the extension.

Therefore, on December 18, 2023, OHAA determined not to further extend the term it has to complete an initial business combination and instead announced its intention to dissolve and liquidate.

On December 28, 2023, all OHAA Class A ordinary shares were cancelled with shareholders receiving their respective share redemption amounts.

Accordingly, there were no “Redeemable non-controlling interests” or restricted cash balances associated with the publicly held OHAA Class A ordinary shares recorded on the Company’s consolidated balance sheet as of December 31, 2023.

The remaining steps of OHAA’s dissolution are expected to be completed in the first quarter of 2024.

Oppenheimer Principal Investments LLC

Oppenheimer Principal Investments LLC ("OPI") is a Delaware special purpose "Series" limited liability company formed in December 2020 and designed to retain and reward talented employees of the Company, primarily in connection with the deployment of Company capital into successful private market investments, and also in connection with the Company's receipt

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

of non-cash compensation from investment banking assignments.

OPI is designed to promote alignment of Company, client and employee interests as they relate to profitable investment opportunities.

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Participating employees are also subject to vesting and forfeiture requirements for each Series investment.

The Company’s policy is to consolidate those entities where it owns the majority voting interests.

The Company owns the majority voting interest of OPI through Oppenheimer Alternative Investment Management (“OAIM”), the managing member of OPI and a subsidiary of OAM.

Vested profit interests are accounted for as compensation expense under FASB Topic ASC 710.

Additionally, the Company’s policy is to consolidate those entities where it owns the majority voting interests.

The Company owns the majority voting interest of OPI

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

through Oppenheimer Alternative Investment Management (“OAIM”), the managing member of OPI and a subsidiary of OAM.

Pursuant to the Company’s policy for consolidation, the Company consolidates OPI.

Noncontrolling Interests

Noncontrolling interests represents ownership interests in the Sponsor of OHAA which includes OHAA Class A founder and Class A ordinary shares held by management and employees of the Company as well as OHAA Class B shares held by directors and officers of OHAA and an employee of the Company.

Noncontrolling interests also includes the OHAA Warrants and publicly held warrants to purchase OHAA Class A ordinary shares.

For the years ended December 31, 2022 and December 31, 2021, the net loss attributed to noncontrolling interests was $ 241,000 and $ 8,000 (net of taxes), respectively.

Non-controlling Interests

Non-controlling interests represents ownership interests in the Sponsor of OHAA.

For the year ended December 31, 2023, the net gain (net of taxes) attributed to non-controlling interests was $ 93,000 .

For the year ended December 31, 2022, the net loss (net of taxes) attributed to non-controlling interests was$ 241,000 .

Restricted Cash

Restricted cash represents OHAA deposits held in trust as indicated above.

New Accounting Pronouncements

The Company has reviewed and evaluated the impact of the recently issued Accounting Standard Updates by the Financial Accounting Standards Board ("FASB") and noted that they are not expected to have a material impact on its consolidated financial statements and disclosure.

Restricted cash represents OHAA deposits held in trust.

Since these deposits were returned to OHAA’s Class A shareholders as indicated above, there was no restricted cash as of December 31, 2023.

On December 29, 2023, the Company acquired 100 % of the membership interests of BondWave LLC, a cloud-based financial markets software as a service provider that offers institutions active in fixed income markets with an integrated suite of portfolio analytics, transaction analytics and proprietary data solutions.

Under the terms of the agreement, the Company paid approximately $ 3.6 million on closing, with the potential for additional contingent payments to be made within 18 months after the closing date.

The Company accounted for the acquisition under the acquisition method of accounting in accordance with ASC 805, “Business Combinations.” The Company allocated $ 4.3 million of the purchase price to goodwill, $ 2.2 million to definite-lived intangible assets, $ 625 thousand to cash acquired and the remainder to other assets acquired and liabilities assumed as part of the acquisition.

The goodwill, which has been allocated to the “Corporate/Other” segment, primarily reflects the expected synergies of combining the scalable software platform with Oppenheimer’s broader client base.

Financial Instruments - Credit Losses

4 unchanged sentences

As of December 31, 2023, the Company has $ 62.6 million of notes receivable.

Notes receivable represents recruiting and retention payments generally in the form of upfront loans to financial advisors and key revenue producers as part of the Company's overall growth strategy.

Notes receivable primarily represents recruiting and retention payments generally in the form of upfront loans to financial advisors and key revenue producers as part of the Company's overall growth strategy.

These notes generally amortize over a service period of 3 to 10 years from the initial date of the note or based on productivity levels of employees.

4 unchanged sentences

Balances are charged-off against the allowance when management deems the amount to be uncollectible.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The Company reserves 100 % of the uncollected balance of defaulted notes which are five years and older and applies an expected loss rate to the remaining balance.

3 unchanged sentences

The Company will continuously monitor the effect of these factors on the expected loss rate and adjust it as necessary.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The allowance is measured on a pool basis as the Company has determined that the entire defaulted portion of notes receivable has similar risk characteristics.

1 unchanged sentence

The allowance for uncollectibles consisted of $ 1.7 million related to defaulted notes balances (five years and older) and $ 2.2 million (under five years).

The following table presents the disaggregation of defaulted notes by year of origination as of December 31, 2022:

The following table presents the disaggregation of defaulted notes by year of default as of December 31, 2023:

(Expressed in thousands)

7 unchanged sentences

Additions and other adjustments

( 458 ) ( 596 )

Ending balance

$ 3,869 $ 4,327

The Company and its subsidiaries have operating leases for office space and equipment expiring at various dates through 2034.

The Company has operating leases for office space and equipment expiring at various dates through 2034.

The Company leases its corporate headquarters at 85 Broad Street, New York, New York which houses its executive management team and many administrative functions for the firm as well as its research, trading, investment banking, and asset management divisions and an office in Troy, Michigan, which among other things, houses its payroll and human resources departments.

2 unchanged sentences

The Company is constantly assessing its needs for office space and, on a rolling basis, has many leases that expire in any given year.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Substantially all of the leases are held by the Company's subsidiary, Viner Finance Inc., which is a consolidated subsidiary and 100 % owned by the Company.

3 unchanged sentences

The Company did not include the renewal options as part of the right of use assets and liabilities.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The depreciable life of assets and leasehold improvements is limited by the expected lease term.

21 unchanged sentences

Equipment leases - Interest expense 184 152

The maturities of lease liabilities as of December 31, 2023 are as follows:

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The maturities of lease liabilities as of December 31, 2022 are as follows:

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

(Expressed in thousands)

57 unchanged sentences

Notes to Consolidated Financial Statements

(Expressed in thousands) For the Year Ended December 31, 2022

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

For the Year Ended December 31, 2023

Reportable Segments

33 unchanged sentences

Total revenue $ 675,680 $ 99,242 $ 337,821 $ ( 1,802 ) $ 1,110,941

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Contract Assets and Liabilities

2 unchanged sentences

Alternatively, when payment precedes the provision of the related services, the Company records deferred revenue until the performance obligations are satisfied.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The Company had receivables related to revenue from contracts with customers of $ 39.9 million and $ 32.8 million at December 31, 2023 and December 31, 2022, respectively.

The Company had no significant impairments related to these receivables during the years ended December 31, 2023 and 2022.

As of December 31, 2023 and December 31, 2022, the Company had no contract assets.

Deferred revenue relates to IRA fees received annually in advance on customers' IRA accounts managed by the Company and retainer fees and other fees earned from certain advisory transactions where the performance obligations have not yet been satisfied.

Total deferred revenue was $ 900,000 and $ 235,000 for years ended December 31, 2022 and 2021.

The following presents the Company's contract assets and deferred revenue balances from contracts with customers, which are included in other assets and other liabilities, respectively, on the consolidated balance sheet:

Total deferred revenue was $ 1,118,000 and $ 900,000 for years ended December 31, 2023 and 2022, respectively.

The following presents the Company's receivables and deferred revenue balances from contracts with customers, which are included in other assets and other liabilities, respectively, on the consolidated balance sheet:

(Expressed in thousands) As of

December 31, 2023 December 31, 2022

Contract assets (receivables):

Commission (1)

5 unchanged sentences

Other 6,126 4,686

Total contract assets $ 32,773 $ 37,192

Total receivables $ 39,861 $ 32,773

Deferred revenue (payables):

Investment banking fees (6)

$ 1,118 $ 900

Total deferred revenue $ 1,118 $ 900

3 unchanged sentences

(4) Fees earned from FDIC-insured bank deposit program but not yet received.

(5) Underwriting revenue and advisory fees earned but not yet received, including certain receivables.

(6) Retainer fees and fees earned from certain advisory transactions where the performance

obligations have not yet been satisfied.

(5) Underwriting revenue and advisory fees earned but not yet received.

(6) Retainer fees and fees received from certain advisory transactions where the performance obligations have not

yet been satisfied.

Contract Costs

The Company incurs incremental transaction-related costs to obtain and/or fulfill contracts associated with investment banking

and advisory engagements where the revenue is recognized at a point in time and the costs are determined to be recoverable.

The Company incurs incremental transaction-related costs to obtain and/or fulfill contracts associated with investment banking and advisory engagements where the revenue is recognized at a point in time and the costs are determined to be recoverable.

of December 31, 2023, these contract costs were $ 1.9 million ($ 1.4 million as of December 31, 2022).

18 unchanged sentences

Total $ 361,890 $ 550,006

(1) The balances are primarily related to a trade/settlement date adjustment for U.S.

Government Securities.

(1) The balances are primarily related to a trade/settlement date adjustment for positions in inventory.

Fair value measurements

13 unchanged sentences

The fair value of corporate bonds is estimated using recent transactions, broker quotations and bond spread information.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Mortgage and Other Asset-Backed Securities

1 unchanged sentence

When specific external pricing is not observable, the valuation is based on yields and spreads for comparable bonds.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Municipal Obligations

7 unchanged sentences

Auction Rate Securities ("ARS")

In February 2010, Oppenheimer finalized settlements with each of the New York Attorney General's office ("NYAG") and the Massachusetts Securities Division ("MSD" and together with the NYAG, the "Regulators") concluding proceedings by the Regulators concerning Oppenheimer's marketing and sale of ARS.

Pursuant to the settlements with the Regulators, Oppenheimer agreed to extend offers to repurchase ARS from certain of its clients.

As of September 30, 2021, the Company had completed its ARS purchase obligations related to the settlements with the Regulators.

In addition to the settlements with the Regulators, Oppenheimer had also reached settlements of and received adverse awards in legal proceedings with various clients where the Company was obligated to purchase ARS.

As of December 31, 2022, the Company no longer had any obligations to purchase ARS from such legal settlements or adverse awards.

As of December 31, 2023, the Company owned $ 2.7 million of ARS.

This amount represents the unredeemed or unsold amount that the Company holds as a result of ARS buybacks pursuant to the settlements with the Regulators and legal settlements and awards referred to above.

The Company’s ARS owned referred to above have, for the most part, been subject to issuer tender offers.

This represents the amount that the Company holds as a result of ARS buybacks in previous years.

The Company has valued the ARS securities owned at the tender offer price and categorized them in Level 3 of the fair value hierarchy due to the illiquid nature of the securities and the period of time since the last tender offer.

4 unchanged sentences

In its role as general partner in certain hedge funds and private equity funds, the Company, through its subsidiaries, holds direct investments in such funds.

The Company uses the net asset value of the underlying fund as a basis for estimating the fair value of its investment.

The Company records these investments within other assets and uses the net asset value of the underlying fund as a basis for estimating the fair value of its investment unless another method provides a better indicator of fair value.

Changes in the fair value of these investments are reflected within other income in the consolidated financial statements.

OPPENHEIMER HOLDINGS INC.

11 unchanged sentences

$ 5,518 $ 2,367

(1) Includes investments in hedge funds and hedge fund of funds that pursue long/short, event-driven,

and activist strategies.

(1) Includes investments in hedge funds and hedge fund of funds that pursue long/short, event-driven, and activist

(2) Includes private equity funds and private equity fund of funds with diversified portfolios focusing on but not

11 unchanged sentences

$ 8,795 $ 3,018

(1) Includes investments in hedge funds and hedge fund of funds that pursue long/short, event-driven,

and activist strategies.

(1) Includes investments in hedge funds and hedge fund of funds that pursue long/short, event-driven, and activist

(2) Includes private equity funds and private equity fund of funds with diversified portfolios, focusing on but not

limited to technology companies, venture capital and global natural resources.

During 2020, the Company made an investment in a financial technologies firm.

The Company owns an investment in a financial technologies firm.

The Company elected the fair value option for this investment and it is included in other assets on the consolidated balance sheet.

13 unchanged sentences

Agency securities — 2 — 2

Sovereign obligations — 9,502 — 9,502

Corporate debt and other obligations — 5,769 — 5,769

8 unchanged sentences

1,872 16,913 — 18,785

Securities purchased under agreements to resell — 5,842 — 5,842

Derivative contracts:

Futures 2 — — 2

TBAs — 11 — 11

Derivative contracts, total $ 2 $ 11 $ — $ 13

Total $ 764,579 $ 87,449 $ 2,713 $ 854,741

Treasury securities $ 14,603 $ — $ — $ 14,603

Agency securities — 3 — 3

Sovereign obligations — 9,048 — 9,048

Corporate debt and other obligations — 1,508 — 1,508

Mortgage and other asset-backed securities — 2 — 2

Convertible bonds — 2,136 — 2,136

3 unchanged sentences

Futures 735 — — 735

TBAs — 1,761 — 1,761

Derivative contracts, total 735 2 — 737

17 unchanged sentences

Corporate equities 24,837 — — 24,837

Money markets 31 — — 31

Auction rate securities — — 31,776 31,776

8 unchanged sentences

Agency securities — 3 — 3

Sovereign obligations — 9,048 — 9,048

Corporate debt and other obligations — 2,905 — 2,905

8 unchanged sentences

(1) Included in other assets on the consolidated balance sheet.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The following tables present changes in Level 3 assets and liabilities measured at fair value on a recurring basis for the years ended December 31, 2023 and 2022:

4 unchanged sentences

and Unrealized

Losses (3)(4)

and Issuances Sales and Settlements Transfers

2 unchanged sentences

$ 31,776 $ 3,159 $ — $ ( 32,222 ) $ — $ 2,713

ARS purchase commitments (2)

(1) Represents auction rate securities that failed in the auction rate market.

(2) Represents the difference in principal and fair value for auction rate securities purchase commitments

outstanding at the end of the period.

(2) Included in principal transactions in the consolidated income statement.

(4) Unrealized losses are attributable to assets or liabilities that are still held at the reporting date.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

(Expressed in thousands)

7 unchanged sentences

$ 31,804 $ ( 28 ) $ 1,375 $ ( 1,375 ) $ — $ 31,776

ARS purchase commitments (2)

195 ( 1 ) — ( 196 ) — —

(1) Represents auction rate securities that failed in the auction rate market.

(2) Represents the difference in principal and fair value for auction rate securities purchase commitments

outstanding at the end of the period.

(2) Included in principal transactions in the consolidated income statement.

(4) Unrealized losses are attributable to assets or liabilities that are still held at the reporting date.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Financial Instruments Not Measured at Fair Value

6 unchanged sentences

Carrying Value Level 1 Level 2 Level 3 Total

Cash $ 112,433 $ 112,433 $ — $ — $ 112,433

Restricted cash 25,534 25,534 — — 25,534

Cash and cash equivalents $ 28,835 $ 28,835 $ — $ — $ 28,835

Deposits with clearing organization 43,917 43,917 — — 43,917

9 unchanged sentences

90,999 — 90,999 — 90,999

(1) Included in other assets on the consolidated balance sheet.

(1) The cash surrender value of Company-owned life insurance policies, which fluctuates based on changes in fair

value of the policies’ underlying investments, comprises approximately $ 89 million of this balance.

is included within other assets on the consolidated balance sheet.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

(Expressed in thousands) Fair Value Measurement:

Carrying Value Level 1 Level 2 Level 3 Total

Bank call loans $ — $ — $ — $ — $ —

Drafts payable $ 9,002 $ 9,002 $ — $ — $ 9,002

Payables to brokers, dealers and clearing organizations:

2 unchanged sentences

Securities failed to receive 23,809 — 23,809 — 23,809

Other 166,350 — 166,350 — 166,350

Clearing Organizations and Other 51,912 — 51,912 — 51,912

$ 361,155 — $ 361,155 — $ 361,155

2 unchanged sentences

Senior secured notes 113,050 — 109,838 — 109,838

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Assets and liabilities not measured at fair value as of December 31, 2022

1 unchanged sentence

Carrying Value Level 1 Level 2 Level 3 Total

Cash $ 213,759 $ 213,759 $ — $ — $ 213,759

Cash and cash equivalents $ 112,433 $ 112,433 $ — $ — $ 112,433

Restricted cash 25,534 25,534 — — 25,534

5 unchanged sentences

Clearing organizations 20,035 — 20,035 — 20,035

Other 1,693 — 1,693 — 1,693

206,076 — 206,076 — 206,076

Receivable from customers 1,202,764 — 1,202,764 — 1,202,764

Securities purchased under agreements to resell 935 — 935 — 935

Notes receivable, net 57,495 — 57,495 — 57,495

1 unchanged sentence

79,322 — 79,322 — 79,322

(1) Included in other assets on the consolidated balance sheet.

(1) The cash surrender value of Company-owned life insurance policies, which fluctuates based on changes in fair

value of the policies’ underlying investments, comprises approximately $ 77 million of this balance.

is included within other assets on the consolidated balance sheet.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

(Expressed in thousands) Fair Value Measurement:

Carrying Value Level 1 Level 2 Level 3 Total

Bank call loans 69,500 — 69,500 — 69,500

Payables to brokers, dealers and clearing organizations:

15 unchanged sentences

Such hedges have not been designated as accounting hedges.

Unrealized gains and losses on foreign exchange forward contracts are

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

recorded in other assets or other liabilities on the consolidated balance sheet and other income in the consolidated income statement.

Unrealized gains and losses on foreign exchange forward contracts are recorded in other assets or other liabilities on the consolidated balance sheet and other income in the consolidated income statement.

Derivatives used for trading and investment purposes

10 unchanged sentences

Net unrealized gains and losses on TBAs are recorded on the consolidated balance sheet in receivable from brokers, dealers and clearing organizations or payable to brokers, dealers and clearing organizations and in the consolidated income statement as principal transactions revenue, net.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The notional amounts and fair values of the Company's derivatives as of December 31, 2023 and 2022 by product were as follows:

4 unchanged sentences

Other contracts TBAs $ 3,700 $ 11

Forward reverse repurchase agreements 15,000 —

$ 17,050 $ 1,762

Commodity contracts

Futures 5,000 2

Derivatives not designated as hedging instruments (1)

3 unchanged sentences

$ 6,878,700 $ 737

(1) See "Derivative Instruments and Hedging Activities" above for a description of derivative financial

Such derivative instruments are not subject to master netting agreements, thus the related

amounts are not offset.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

(1) See "Derivative Instruments and Hedging Activities" above for a description of derivative financial instruments.

Such derivative instruments are not subject to master netting agreements, thus the related amounts are not offset.

(Expressed in thousands)

3 unchanged sentences

Other contracts TBAs $ 1,775 $ 1,762

Forward reverse repurchase agreements 15,000 —

$ 17,050 $ 1,762

4 unchanged sentences

$ 1,914,275 $ 1,805

(1) See "Derivative Instruments and Hedging Activities" above for a description of derivative financial

Such derivative instruments are not subject to master netting agreements, thus the related

amounts are not offset.

(1) See "Derivative Instruments and Hedging Activities" above for a description of derivative financial instruments.

Such derivative instruments are not subject to master netting agreements, thus the related amounts are not offset.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The following table presents the location and fair value amounts of the Company's derivative instruments and their effect in the consolidated income statements for the years ended December 31, 2023 and 2022:

2 unchanged sentences

For the Year Ended December 31, 2023

Types Description Location Net Gain (Loss)

Types Description Location Net Gain

Commodity contracts Futures Principal transactions revenue $ 2,842

8 unchanged sentences

TBAs Principal transactions revenue 60

Purchase commitments Principal transactions revenue ( 987 )

ARS purchase commitments Principal transactions revenue ( 1 )

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Collateralized transactions

5 unchanged sentences

Bank call loans are generally payable on demand and bear interest at various rates.

As of December 31, 2022, the outstanding balance of bank call loans was zero ($ 69.5 million as of December 31, 2021).

As of December 31, 2022, the Company had approximately $ 1.7 billion of customer securities under customer margin loans that are available to be pledged, of which the Company has re-pledged approximate ly $ 268.2 milli on under securities loan agreements.

As of December 31, 2023 and 2022, the outstanding balance of bank call loans was zero .

As of December 31, 2023, the Company had approximately $ 1.6 billion of customer securities under customer margin loans that are available to be pledged, of which the Company has re-pledged approximately $ 211.3 million under securities loan agreements.

As of December 31, 2023, the Company had pledged $ 129.2 million of customer securities directly with the Options Clearing Corporation to secure obligations and margin requirements under option contracts written by customers.

4 unchanged sentences

Repurchase agreements and reverse repurchase agreements are presented on a net-by-counterparty basis, when the repurchase agreements and reverse repurchase agreements are executed with the same counterparty, have the same explicit settlement date, are executed in accordance with a master netting arrangement, the securities underlying the repurchase agreements and reverse repurchase agreements exist in "book entry" form and certain other requirements are met.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The following table presents a disaggregation of the gross obligation by the class of collateral pledged and the remaining contractual maturity of the repurchase agreements and securities loaned transactions as of December 31, 2023:

6 unchanged sentences

Gross amount of recognized liabilities for repurchase agreements and securities loaned $ 928,397

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The following tables present the gross amounts and the offsetting amounts of reverse repurchase agreements, repurchase agreements, securities borrowed and securities loaned transactions as of December 31, 2023 and 2022:

38 unchanged sentences

Total $ 155,829 $ ( 28,012 ) $ 127,817 $ ( 127,365 ) $ — $ 452

(1) Included in receivable from brokers, dealers and clearing organizations on the consolidated balance sheet.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

(1) Included in receivable from brokers, dealers and clearing organizations on the consolidated balance

Gross Amounts Not Offset

11 unchanged sentences

(2) Included in payable to brokers, dealers and clearing organizations on the consolidated balance sheet.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The Company elects the fair value option for those repurchase agreements and reverse repurchase agreements that do not settle overnight or have an open settlement date.

As of December 31, 2022, the Company did not have any repurchase agreements and reverse repurchase agreements that do not settle overnight or have an open settlement date.

The Company receives collateral in connection with securities borrowed and reverse repurchase agreement transactions and customer margin loans.

2 unchanged sentences

The Company pledges certain of its securities owned for securities lending and repurchase agreements and to collateralize bank call loan transactions.

The carrying value of pledged securities owned that can be sold or re-pledged by the counterparty was $ 175.7 million, a s presented on the face of the consolidated balance sheet as of December 31, 2022 ($ 266.4 million as of December 31, 2021).

The carrying value of pledged securities owned that can be sold or re-pledged by the counterparty was $ 689.4 million, as presented on the face of the consolidated balance sheet as of December 31, 2023 ($ 175.7 million as of December 31, 2022).

The Company manages credit exposure arising from repurchase and reverse repurchase agreements by, in appropriate circumstances, entering into master netting agreements and collateral arrangements with counterparties that provide the Company, in the event of a customer default, the right to liquidate securities and the right to offset a counterparty's rights and obligations.

6 unchanged sentences

The Company seeks to mitigate these risks by actively monitoring exposures and obtaining collateral as deemed appropriate.

Included in receivable from brokers, dealers and clearing organizations as of December 31, 2022 are receivables f rom 5 major U.S.

Included in receivable from brokers, dealers and clearing organizations as of December 31, 2023 are receivables f ro m three major U.S.

broker-dealers totaling approximately $ 107.6 million.

2 unchanged sentences

If clients do not fulfill their contractual obligations, the Company may incur losses.

The Company has clearing/participating arrangements with the National Securities Clearing Corporation, the Fixed Income Clearing Corporation ("FICC"), R.J.

O'Brien & Associates (commodities transactions), Mortgage-Backed Securities Division (a division of FICC) and others.

The Company has clearing/participating arrangements with the National Securities Clearing Corporation, the Fixed Income Clearing Corporation ("FICC"), the Mortgage-Backed Securities Division (a division of FICC) and others.

With respect to its business in reverse repurchase and repurchase agreements, substantially all open contracts as of December 31, 2023 are with the FICC .

1 unchanged sentence

international equities business carried on by Oppenheimer Europe Ltd.

through Global Prime Partners, Ltd, a global clearing financial institution located in United Kingdom.

through Global Prime Partners, Ltd, a global clearing financial institution located in the United Kingdom.

The clearing organizations have the right to charge the Company for losses that result from a client's failure to fulfill its contractual obligations.

Accordingly, the Company has credit exposures with these clearing brokers.

The clearing brokers can re-hypothecate the securities held on behalf of the Company.

The clearing brokers can re-hypothecate the

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

securities held on behalf of the Company.

As the right to charge the Company has no maximum amount and applies to all trades executed through the clearing brokers, the Company believes there is no maximum amount assignable to this right.

1 unchanged sentence

The Company's policy is to monitor the credit standing of the clearing brokers and banks with which it conducts business.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Variable interest entities ("VIEs")

9 unchanged sentences

They are sponsors of two special purpose acquisition companies, OHAA and Oppenheimer Acquisition Corp.

II (the "SPACs”), that are seeking to effect a transaction which could be in the form of a merger, capital stock exchange, asset acquisition, stock purchase, reorganization or similar business combination with one or more businesses.

The Sponsors and the SPACs are consolidated VIE's as the Company is the primary beneficiary.

On October 26, 2021, OHAA consummated its $ 126.5 million IPO.

The Company and its employees control OHAA through the Sponsor’s ownership of Class A founder shares of OHAA.

As a result, both OHAA and the Sponsor are consolidated in the Company’s financial statements.

II (the "SPACs”).

Both the Sponsors and the SPACs are in the process of liquidating and dissolving, as indicated above.

Until the liquidation and dissolutions are complete, the Sponsors and the SPACs will remain consolidated VIE's as the Company is the primary beneficiary.

See note 2 for further details.

In connection with its proposal to amend its certificate of incorporation, OHAA was required to give its Class A stockholders the opportunity to redeem their shares of Class A common stock.

Of the 12,650,000 shares of Class A common stock that were outstanding, a total of 10,170,490 shares exercised their redemption rights.

As of December 31, 2022, $ 25.5 million remained in the trust account that is recorded within “Restricted Cash” on the consolidated balance sheet.

The following table sets forth the total assets and liabilities of VIE's consolidated on our consolidated balance sheet:

39 unchanged sentences

The Company used the net proceeds from the offering of the Unregistered Notes, along with cash on hand, to redeem in full our 6.75 % Senior Secured Notes due July 1, 2022 (the "Old Notes") in the principal amount of $ 150.0 million (the Company held $ 1.4 million in treasury for a net outstanding amount of $ 148.6 million), and pay all related fees and expenses in relation thereto.

On November 23, 2020, we completed an exchange offer in which we exchanged 99.8 % of the Unregistered Notes for a like principal amount of Notes with identical terms, except that such new notes have been registered under the Securities Act of 1933, as amended (the "Securities Act").

We did not receive any proceeds in the exchange offer.

The Notes will mature on

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

October 1, 2025 and bear interest at a rate of 5.50 % per annum, payable semiannually on April 1st and October 1st, respectively, of each year.

did not receive any proceeds in the exchange offer.

The Notes will mature on October 1, 2025 and bear interest at a rate of 5.50 % per annum, payable semiannually on April 1st and October 1st, respectively, of each year.

The Parent used the net proceeds from the offering of the Notes, along with cash on hand, to redeem in full its Old Notes, in the principal amount of $ 150.0 million (the Parent held $ 1.4 million in treasury for a net outstanding amount of $ 148.6 million), and pay all related fees and expenses in relation thereto.

3 unchanged sentences

Such repurchases, if any, will depend on a number of factors, including, but not limited to, the Company’s priorities for the use of cash, price, market and economic conditions, its liquidity requirements, and legal and contractual restrictions.

As of December 31, 2022, the Company repurchased and cancelled $ 10.95 million aggregate principal amount of its Notes in the open market.

During the year-ended December 31, 2022, the Company repurchased and cancelled $ 10.95 million aggregate principal amount of its Notes in the open market.

During the first quarter of 2023, the Company repurchased and cancelled an additional $ 1.0 million aggregate principal amount of its Notes in the open market.

As of December 31, 2023, $ 113.05 million aggregate principal amount of the Notes remain outstanding.

28 unchanged sentences

Interest paid on the Notes for the year ended December 31, 2023 was $ 6.2 million ($ 6.7 million for the year ended December 31, 2022).

6.75 % Senior Secured Notes (the "Old Notes")

On June 23, 2017, the Parent issued in a private offering $ 200.0 million aggregate principal amount of 6.75 % Senior Secured Notes due 2022 under an indenture at an issue price of 100 % of the principal amount.

Interest on the Old Notes was payable semi-annually on January 1st and July 1st, beginning January 1, 2018.

The Company redeemed $ 50.0 million ( 25 %) of the Old Notes on August 25, 2019 plus accrued and unpaid interest and incurred $ 1.9 million in costs associated with paying the associated call premium ($ 1.7 million) and the write-off of debt issuance costs ($ 0.2 million) during the third quarter of 2019.

During the first quarter of 2020, the Company repurchased $ 1.4 million of the Old Notes.

The Company recorded a gain of $ 85,560 on the repurchase during the first quarter of 2020.

The Old Notes were scheduled to mature on July 1, 2022.

On August 28, 2020, the Parent issued a conditional notice of redemption to redeem the entire $ 150.0 million aggregate principal amount of the outstanding Old Notes on September 28, 2020 (the “Redemption Date”).

On September 28, 2020, the Old Notes were fully redeemed.

Interest expense and interest paid on the Old Notes for the year ended December 31, 2020 was $ 7.4 million.

Stockholders' Equity

8 unchanged sentences

Issued pursuant to share-based compensation plans (note 17) 218,745 105,807

Repurchased and canceled pursuant to the stock buy-back ( 1,684,287 ) ( 177,192 )

Repurchased and canceled ( 900,518 ) ( 1,684,287 )

Class A Stock outstanding, end of year 10,186,783 10,868,556

Stock buy-back

On May 15, 2020, the Company announced that its Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 530,000 shares of the Company's Class A Stock, representing approximately 4.2 % of its 12,636,523 then issued and outstanding shares of Class A Stock.

This authorization supplemented the 98,625 shares that remained authorized and available under the Company's previous share repurchase program for a total of 628,625 shares authorized and available for repurchase at May 15, 2020.

On February 28, 2022, the Company announced that its Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 518,000 shares of the Company's Class A Stock, representing approximately 4.2 % of its 12,322,073 then issued and outstanding shares of Class A Stock.

This authorization supplemented the 12,407 shares that

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

remained authorized and available under the Company's previous share repurchase program for a total of 530,407 shares authorized and available for repurchase at February 28, 2022.

This authorization supplemented the 12,407 shares that remained authorized and available under the Company's previous share repurchase program for a total of 530,407 shares authorized and available for repurchase at February 28, 2022.

On May 24, 2022, the Company announced that its Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 550,000 shares of the Company's Class A Stock, representing approximately 4.6 % of its 11,863,559 then issued and outstanding shares of Class A Stock.

4 unchanged sentences

This authorization supplemented the 144,034 shares that remained authorized and available under the Company's previous share repurchase program for a total of 687,034 shares authorized.

During the year ended December 31, 2022, the Company purchased and canceled an aggregate of 1,684,287 ( 15 %) shares of Class A Stock for a total consideration of $ 60.6 million ($ 36.00 per share).

As of December 31, 2022, 687,034 shares remained available to be purchased under its share repurchase program.

During the year ended December 31, 2021, the Company purchased and canceled an aggregate of 177,192 shares of Class A Stock for a total consideration of $ 7.7 million ($ 43.67 per share).

On May 31, 2023, the Company announced the commencement of a modified “Dutch Auction” tender offer to purchase up to $ 30.0 million of its Class A Stock at a price not less than $ 34.00 per share or more than $ 40.00 per share.

The Company completed its repurchases pursuant to the tender offer on July 6, 2023, when it successfully repurchased and cancelled 437,183 shares of Class A Stock at $ 40.00 per share for an aggregate purchase price of $ 17.49 million.

As a result, the Company had 10,447,392 shares outstanding on July 6, 2023 after the purchase.

During the year ended December 31, 2023, the Company purchased and canceled an aggregate of 463,335 shares of Class A Stock for a total consideration of $ 17.6 million ($ 38.07 per share) under its share repurchase program.

As of December 31,

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

2023, 223,699 shares remained available to be purchased under its share repurchase program.

During the year ended December 31, 2022, the Company purchased and canceled an aggregate of 1,684,287 shares of Class A Stock for a total consideration of $ 60.6 million ($ 36.00 per share) under its share repurchase program.

As of December 31, 2022, 687,034 shares remained available to be purchased under the share repurchase program.

On March 1, 2024, the Company's Board of Directors approved a share repurchase program that authorizes the Company to purchase up to 442,711 shares of the Company's Class A Stock, representing approximately 5.0 % of its 10,357,376 then issued and outstanding shares of Class A Stock.

This authorization supplemented the 223,699 shares that remained authorized and available under the Company's previous share repurchase program for a total of 666,410 shares authorized.

Share purchases will be made by the Company from time to time in the open market at the prevailing open market price using cash on hand, in compliance with the applicable rules and regulations of the New York Stock Exchange and federal and state securities laws and the terms of the Company's Notes.

5 unchanged sentences

The Company paid cash dividends of $ 0.60 per share in 2023 to holders of Class A and Class B Stock, in the aggregate amount of 6.5 million.

In 2021, the Company paid cash dividends of $ 1.54 per share which includes a special cash dividend of $ 1.00 per share paid on December 31, 2021 in the aggregate amount of $ 19.4 million.

The Company paid cash dividends of $ 0.60 per share in 2022 in the aggregate amount of $ 7.0 million.

In 2021, the Company paid cash dividends of $ 1.54 per share which includes a special cash dividend of $ 1.00 per share paid on December 31, 2021 in the aggregate amount of $ 19.4 million.

Earnings per share

Basic earnings per share is computed by dividing net income over the weighted average number of shares of Class A non-voting common stock ("Class A Stock") and Class B voting common stock ("Class B Stock") outstanding.

Basic earnings per share is computed by dividing net income over the weighted average number of shares of Class A Stock and Class B Stock outstanding.

Diluted earnings per share includes the weighted average number of shares of Class A Stock and Class B Stock outstanding and options to purchase Class A Stock and unvested restricted stock awards of Class A Stock using the treasury stock method.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Earnings per share have been calculated as follows:

12 unchanged sentences

(1) For the year ended December 31, 2023, the diluted net income per share computation did not include the anti-dilutive effect of 115,950 shares of Class A Stock granted under share-based compensation arrangements.

For the year ended December 31, 2022, the diluted net income per share computation did not include the anti-dilutive

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

effect of 4,100 shares of Class A Stock granted under share-based compensation arrangements.

For the year ended December 31, 2021, there was no Class A Stock granted under share-based compensation arrangements that were anti-dilutive.

For the year ended December 31, 2020, the diluted net income per share computation did not include the anti-dilutive effect of 10,770 shares of Class A Stock granted under share-based compensation arrangements.

Income tax expenses shown in the consolidated income statements are reconciled to amounts of tax that would have been payable from the application of the federal tax rate to pre-tax profit, as follows:

17 unchanged sentences

Income tax expenses included in the consolidated income statements represent the following:

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

(Expressed in thousands)

12 unchanged sentences

operations was $ 4.8 million for the year ended December 31, 2023.

(Pre-tax loss with respect to non-U.S.

operation was $ 1.2 million for the year ended December 31, 2021).

Pre-tax income with respect to non-U.S.

operation was $ 7.7 million for the year ended December 31, 2022.

Pre-tax loss with respect to non-U.S.

operations was $ 1.2 million for the year ended December 31, 2021.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The effective income tax rate for the year ended December 31, 2023 was 35.3 % compared with 29.5 % for the year ended December 31, 2022.

The higher tax rate in the 2022 year was primarily due to the impact of unfavorable permanent items.

The higher tax rate in the 2023 year was primarily due to the im pact of unfavorable permanent items.

Deferred income taxes reflect the net tax effects of temporary differences between the financial reporting and tax bases of assets and liabilities and are measured using enacted tax rates and laws that will be in effect when such differences are expected to reverse.

22 unchanged sentences

Deferred tax liabilities, net $ ( 36,335 ) $ ( 29,804 )

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

The Company recognized deferred tax assets of $ 2 million at December 31, 2023 within other assets arising from net operating losses incurred by Oppenheimer Israel (OPCO) Ltd.

3 unchanged sentences

The net change during the year in the total valuation allowance is $ 3.4 million.

Goodwill arising from the acquisitions of Josephthal Group Inc.

and the Oppenheimer Divisions was amortized for tax purposes on a straight-line basis over 15 years.

The difference between book and tax is recorded as a deferred tax liability.

The Company and one or more of its subsidiaries files income tax returns in the U.S.

4 unchanged sentences

Included in the balance of unrecognized tax benefits as of December 31, 2023 and 2022 were $ 977,000 and $ 847,000 , respectively, of tax benefits for either year that, if recognized, would affect the effective tax rate.

During the year ended December 31, 2022, the Company added $ 0.7 million related to state and local tax matters.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

During the year ended December 31, 2023, the Company adde d $ 0.2 million and released $ 0.1 million related to state and local tax matters.

The Company does not believe any unrecognized tax benefit will significantly increase or decrease within twelve months.

7 unchanged sentences

In its consolidated income statements, the Company records interest and penalties accruing on unrecognized tax benefits in pre-tax income as interest expense and other expense, respectively.

For the year ended December 31, 2022, the Company added tax-related interest expense of $ 173,000 , and for the years ended December 2021 and 2020 , the Company released tax-related interest expense of $ 164,000 and $ 227,000 , respectively, in its consolidat ed income statement.

As of December 31, 2022 and 2021, the Company had an income tax-related interest payable o f $ 214,000 and $ 41,000 , respectively, on its consolidated balance sheets.

For the year ended December 31, 2023, the Company added tax-related interest expense of $ 107,000 , and for the years ended December 2022 and 2021, the Company released tax-related interest expense of $ 173,000 and $ 164,000 , respectively, in its consolidated income statement.

As of December 31, 2023 and 2022, the Company had an income tax-related interest payable of $ 322,000 and $ 214,000 , respectively, on its consolidated balance sheets.

Employee compensation plans

6 unchanged sentences

2014 Incentive Plan (the "OIP").

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

awards") to or for the benefit of employees and non-employee directors of the Company and its subsidiaries as part of their compensation.

Pursuant to the OIP, the Compensation Committee of the Board of Directors of the Company (the "Committee") is permitted to grant options to purchase Class A Stock ("stock options"), Class A Stock awards and restricted Class A Stock (collectively "restricted stock awards") to or for the benefit of employees and non-employee directors of the Company and its subsidiaries as part of their compensation.

Stock o ptions are generally granted for a five-year term and generally vest at the rate of 25 % of the amount granted on the second anniversary of the grant, 25 % on the third anniversary of the grant, 25 % on the fourth anniversary of the grant and 25 % on the six months before expiration.

Restricted stock awards are generally awarded for a three or five year term and fully vest at the end of the term.

Oppenheimer Holdings Inc.

Stock Appreciation Right Plan

Under the Oppenheimer Holdings Inc.

Stock Appreciation Right Plan, the Company awards stock appreciation rights ("OARs") to certain employees as part of their compensation package based on a formula reflecting gross production and length of service.

These awards are granted once per year in January with respect to the prior year's production.

The OARs vest five years from grant date and settle in cash at vesting.

Restricted stock - The Company has granted restricted stock awards pursuant to the OIP.

10 unchanged sentences

The aggregate intrinsic value of restricted Class A Stock awards outstanding as of December 31, 2023 was $ 65.7 million.

During the year ended December 31, 2022, the Company included $ 11.5 million ($ 10.5 million in 2021 and $ 7.7 million in 2020) of compensation expense in its consolidated income statements relating to restricted Class A Stock awards.

During the year ended December 31,

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

2023, the Company included $ 13.1 million ($ 11.5 million in 2022 and $ 10.5 million in 2021) of compensation expense in its consolidated income statements relating to restricted Class A Stock awards.

As of December 31, 2023, there was $ 21.4 million of total unrecognized compensation cost related to unvested restricted Class A Stock awards.

1 unchanged sentence

As of December 31, 2023, the number of shares of Class A Stock available under the share-based compensation plans, but not yet awarded, was 145,303 .

On May 8, 2023, holders of the Class B voting common stock of the Company voted to approve increasing the number of shares of Class A Stock available to the 2014 Plan by 1,250,000 shares of Class A Stock.

On January 24, 2024, the Company registered these additional shares of Class A Stock to be available under the 2014 Plan.

As of January 24, 2024, the number of shares of Class A Stock available under the share-based compensation plans, but not yet awarded, was 1,395,303 .

On January 25, 2024, the Company awarded a total of 311,140 restricted shares of Class A Stock to current employees pursuant to the OIP.

3 unchanged sentences

There were 2,447 and 5,233 options outstanding as of December 31, 2023 and 2022, respectively.

In the year ended December 31, 2022, the Company included $ 15,702 ($ 21,669 in 2021 and $ 25,300 in 2020) of compensation expense in its consolidated income statements relating to the expensing of stock options.

During the year ended December 31, 2023, the Company included $ 8,195 ($ 15,702 in 2022 and $ 21,669 in 2021) of compensation expense in its consolidated income statements relating to the expensing of stock options.

On February 26, 2024 the OIP expired by its terms.

Awards issued prior to the expiration of the OIP survive the termination of the OIP.

Authorized but unissued shares under the OIP not subject to awards were cancelled.

On March 1, 2024 the Board of Directors of the Company approved the Company’s 2024 Incentive Plan (“2024 Plan”) subject to approval of the 2024 Plan at the Annual Meeting of Stockholders on May 6, 2024.

Oppenheimer Holdings Inc.

Stock Appreciation Right Plan

Under the Oppenheimer Holdings Inc.

These awards are granted once per year in January with respect to the prior year's production.

The OARs vest five years from grant date and settle in cash at vesting.

OARs - The Company has awarded OARs pursuant to the Oppenheimer Holdings Inc.

1 unchanged sentence

The following table summarizes the status of the Company's outstanding OARs awards as of December 31, 2023:

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Grant Date Number of

9 unchanged sentences

The fair value as of December 31, 2023 for each of the OARs was estimated using the Black-Scholes model with the following assumptions:

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

January 11, 2019 January 10, 2020 January 11, 2021 January 7, 2022 January 6, 2023

30 unchanged sentences

The Company maintains an Executive Deferred Compensation Plan ("EDCP") and a Deferred Incentive Plan ("DIP") in order to offer certain qualified high-performing financial advisors a bonus based upon a formula reflecting years of service, production, net commissions and a valuation of their clients' assets.

The bonus amounts resulted in deferrals for fiscal 2022 of

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

$ 11.1 million ($ 12.8 million in 2021 and $ 10.0 million in 2020).

The bonus amounts resulted in deferrals for fiscal 2023 of $ 10.1 million ($ 11.1 million in 2022 and $ 12.8 million in 2021).

These deferrals normally vest after five years .

The liability is being recognized on a straight-line basis over the vesting period.

The liability is being recognized over the vesting period.

The EDCP also includes voluntary deferrals by senior executives that are not subject to vesting.

1 unchanged sentence

The EDCP liability is being tracked against the value of a benchmark investment portfolio held for this purpose.

As of December 31, 2022, the Company's liability with respect to the EDCP, DIP and CMDP totaled $ 53.6 million and is included in accrued compensation on the consolidated balance sheet as of December 31, 2022.

In addition, the Company is maintaining a deferred compensation plan on behalf of certain employees who were formerly employed by CIBC World Markets.

Additionally, the Company maintains the Oppenheimer & Co.

Investment Banking and Capital Markets Deferred Compensation Plan ("CMDP") for eligible employees in the Capital Markets business segment.

As of December 31, 2023, the Company's liability with respect to the EDCP, DIP and CMDP described below totaled $ 69.7 million and is included in accrued compensation on the consolidated balance sheet as of December 31, 2023.

On October 26, 2023 the Company terminated the DIP.

All deferrals made prior to October 26, 2023 survive the termination of the DIP.

The Company also maintains a deferred compensation plan on behalf of certain employees who were formerly employed by CIBC World Markets.

The Company hedges this deferred compensation obligation with a portfolio of mutual fund investments.

As of December 31, 2023, the Company's liability with respect to this plan totaled $ 19.8 million.

On December 15, 2021, the Company adopted the Oppenheimer & Co.

Investment Banking and Capital Markets Deferred Compensation Plan ("CMDP") for eligible employees in the Capital Markets business segment.

An employee is eligible to participate in the Plan if the employee (i) is an Investment Banking Division employee of Oppenheimer with a title of Associate or above whose previous year’s salary and bonus exceeded $ 200,000 , or (ii) is a professional working in the Oppenheimer Capital Markets Division (but not the Investment Banking Division) who is designated by the Plan Administrator (in its sole discretion) as eligible to participate in the Plan.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

An employee is eligible to participate in the CMDP if the employee (i) is an Investment Banking Division employee of Oppenheimer with a title of Associate or above whose previous year’s salary and bonus exceeded $ 200,000 , or (ii) is a professional working in the Oppenheimer Capital Markets Division (but not the Investment Banking Division) who is designated by the Plan Administrator (in its sole discretion) as eligible to participate in the Plan.

The CMDP has both mandatory and elective contributions.

5 unchanged sentences

The Elective Deferral Credit and the Matching Credit are distributed in lump sums in the year following the fifth or tenth anniversary of the last day of the Performance Year (as defined in the CMDP), depending on the participant’s election.

At December 31, 2022, the Company’s deferral related to the CMDP totaled $ 9.3 million which is comprised of Bonus Deferral Credits.

Eligibility for Elective Deferral Credits begins in 2023 for elections made by December 31, 2021.

For fiscal 2023, the Company’s deferral related to the CMDP totaled $ 9.9 million which is comprised of Bonus Deferral Credits.

Eligibility for Elective Deferral Credits began in 2023 for elections made by December 31, 2021.

The total amount expensed in 2023 for the Company's deferred compensation plans was $ 33.6 million ($ 5.3 million in 2022 and $ 18.4 million in 2021).

8 unchanged sentences

The Company is also involved, from time to time, in other reviews, investigations and proceedings (both formal and informal) by governmental and self-regulatory agencies regarding the Company's business, which may result in expenses, adverse judgments, settlements, fines, penalties, injunctions or other relief.

The investigations include inquiries from the SEC, the Financial Industry Regulatory Authority ("FINRA") and various state regulators.

The investigations include inquiries from the SEC, the Financial Industry Regulatory Authority ("FINRA") and other regulators.

The Company accrues for estimated loss contingencies related to legal and regulatory matters within Other Expenses in the consolidated income statement when available information indicates that it is probable a liability had been incurred and the Company can reasonably estimate the amount of that loss.

In many proceedings, however, it is inherently difficult to determine whether any loss is probable or even possible or to estimate the amount of any loss.

In addition, even where a loss is possible or

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

an exposure to loss exists in excess of the liability already accrued with respect to a previously recognized loss contingency, it is often not possible to reasonably estimate the size of the possible loss or range of loss or possible additional losses or range of additional losses.

In addition, even where a loss is possible or an exposure to loss exists in excess of the liability already accrued with respect to a previously recognized loss contingency, it is often not possible to reasonably estimate the size of the possible loss or range of loss or possible additional losses or range of additional losses.

For certain legal and regulatory proceedings, the Company cannot reasonably estimate such losses, particularly for proceedings that are in their early stages of development or where plaintiffs seek substantial, indeterminate or special damages.

Counsel may be required to review, analyze and resolve numerous issues, including through potentially lengthy discovery and determination of important factual matters, and by addressing novel or unsettled legal questions relevant to the proceedings in question, before the Company can reasonably estimate a loss or range of loss or additional loss for the proceeding.

Even after lengthy review and analysis, the Company, in many legal and regulatory proceedings, may not be able to reasonably estimate possible losses or range of loss.

Even after lengthy review

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

and analysis, the Company, in many legal and regulatory proceedings, may not be able to reasonably estimate possible losses or range of losses.

For certain other legal and regulatory proceedings, the Company can estimate possible losses, or range of loss in excess of amounts accrued, but does not believe, based on current knowledge and after consultation with counsel, that such losses individually, or in the aggregate, will have a material adverse effect on the Company's consolidated financial statements as a whole.

4 unchanged sentences

Accordingly, the Company's estimate will change from time to time, and actual losses may be more than the current estimate.

Beginning on or about August 31, 2021, Oppenheimer has been named as a respondent in thirty-seven arbitrations, many containing multiple claimants, each filed before FINRA, relating to those claimants’ purported investment in Horizon Private Equity, III, LLC (“Horizon”).

On November 18, 2022, Oppenheimer received an information request from the SEC requesting information related to the use of text messaging and similar forms of electronic communications by employees of Oppenheimer and whether those communications were properly retained by Oppenheimer as part of its records preservation requirements relating to the broker-dealer business activities of Oppenheimer.

Subsequently, Oppenheimer received a similar information request from the Commodity Futures Trading Commission (“CFTC”).

On January 4, 2024, Oppenheimer submitted an Offer of Settlement to the SEC.

On February 9, 2024, the SEC issued an order (the “Order”) pursuant to which Oppenheimer will pay a fine in the amount of $ 12 million and agree to certain undertakings.

In addition to the Order Oppenheimer received a waiver of certain statutory disqualifications from the SEC.

On February 7, 2024, Oppenheimer submitted an Offer of Settlement to the CFTC pursuant to which Oppenheimer offered to pay a fine of $ 1 million and agree to certain undertakings.

Beginning on or about August 31, 2021, Oppenheimer was named as a respondent in forty-eight arbitrations, many containing multiple claimants, each filed before FINRA, relating to those claimants’ purported investment in Horizon Private Equity, III, LLC (“Horizon”).

Horizon is alleged to be a fraudulent scheme involving, among others, a former Oppenheimer employee John Woods.

John Woods left Oppenheimer’s employ in 2016 and Oppenheimer never received a complaint or question from any of the investors prior to the Securities and Exchange Commission (“SEC”) bringing a complaint against Woods and his co-conspirators in 2021.

Each investor signed a document acknowledging that Horizon was not an approved Oppenheimer product.

John Woods left Oppenheimer’s employ in 2016 and Oppenheimer never received a complaint or question from any of the investors prior to the SEC bringing a complaint against Woods and his co-conspirators in 2021.

Each investor who was an Oppenheimer client, signed a document acknowledging that Horizon was not an approved Oppenheimer product.

Over a protracted period of time, Woods made multiple false statements to Oppenheimer, to regulators and to a state court.

1 unchanged sentence

Claimants do not allege Oppenheimer received any of the funds invested in Horizon, but rather that Oppenheimer’s purported failure to properly supervise its employees allowed the alleged scheme to occur and continue.

The twenty-six arbitrations still pending claim specific monetary damages allege losses of approximately $ 36.4 million in the aggregate while a few others claim unspecified damages.

Oppenheimer has settled, or settled in principle or an award has been rendered in forty-one of the Horizon-related arbitrations, with approximately one hundred thirty-eight individual complainants.

The aggregate payments for those forty-one arbitrations total approximately $ 87.7 million.

The seven arbitrations still pending claim specific monetary damages and allege losses of approximately $ 7.9 million in the aggregate.

On June 16, 2023, Oppenheimer was served with a complaint in an action entitled John and Cynthia Kearney, John & Tera Sargent, Mike Hall, Individually and as Assignee of 6694 Dawson Blvd, LLC, Thomas and Beverly Crampton, Roy and Shirley

Hill, Billy and Debra Lanter, Larry Lawson, Eugene Lyle, Scott Spence, and Dolores Willoughby v.

Oppenheimer & Co.

Inc., Anne Greene and Gordon Morse, filed in Georgia State Court, Fulton County.

Plaintiffs allege that they were all investors in Horizon.

However, all of the plaintiffs allege that they invested in Horizon after John Woods left Oppenheimer’s employ in 2016 and virtually all of the plaintiffs were not Oppenheimer customers.

Plaintiffs further allege that Oppenheimer, through its inaction and/or misconduct, is responsible for their alleged losses and are seeking unspecified damages sounding in violations of the Georgia RICO statute and negligence per se.

On September 5, 2023, Oppenheimer filed a motion to dismiss the complaint, which is pending before the court.

That same day, Oppenheimer also filed a motion to transfer the case to the Metro

Atlanta Business Case Division, which motion was granted.

Oppenheimer believes these claims to be without merit and intends to defend itself vigorously against these claims.

As previously reported Oppenheimer’s motion to vacate the arbitration award in Donald Robinson, Timothy and Sharon Padden, Rhett Rainey, Kelly A.

Rainey Trust, Toucan Holdings LP, Robert Goodman, Robert Daniel Burgner, Individually and as Trustee of the Burgner Family Charitable Remainder Trust, Douglas Kasemeier, Wesley Callaway, and Billy Loveless v.

Also, on July 17, 2023, Oppenheimer was served with a complaint in an action entitled Mark Del Pico, Elizabeth Del Pico and Surrey Lane Partners GP LLC, as general Partner of Surrey Lane Partners, Ltd.

Oppenheimer & Co.

(the “Robinson Arbitration”) was denied on January 30, 2023.

Oppenheimer has settled, or settled in principle, eleven of the Horizon related arbitrations, including the Robinson Arbitration,with approximately forty-one individual complainants.

The aggregate settlement payments for those eleven arbitrations total approximately $48.6 million.

On June 30, 2022, the Company received a "Wells Notice" from the SEC requesting that Oppenheimer make a written submission to the SEC to explain why Oppenheimer should not be charged with violations of Section 15c2-12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and Rule 15c2-12 thereunder as well as Municipal Securities Rulemaking Board Rules G-17 and G-27 in relation to its sales of municipal notes pursuant to an exemption from continuing disclosure contained in Rule 15c2-12.

Inc., and Michael Mooney , filed in Florida State Court, Sarasota County.

Plaintiffs allege that they were all investors in Horizon;

however, none of the plaintiffs were Oppenheimer customers.

All of the plaintiffs allege that they invested in Horizon years after John Woods left Oppenheimer’s employ in 2016.

Plaintiffs further allege that Oppenheimer, through its inaction and/or misconduct, is responsible for their alleged losses and are seeking unspecified damages from Oppenheimer sounding in negligence per se, Oppenheimer filed a motion to dismiss the complaint.

Rather than respond to Oppenheimer’s motion to dismiss, on January 12, 2024, plaintiffs filed an amended complaint that includes an additional claim of fraud against Oppenheimer.

On February 2, 2024 Oppenheimer filed a motion to dismiss the amended complaint which is pending before the Court.

Oppenheimer believes these claims to be without merit and intends to defend itself vigorously against these claims.

Finally, on August 25, 2023, Oppenheimer was served with a complaint in an action entitled Lisa Wright, Billy Ray Boaz, Sylvia Boyles, Donald and Gina Bryant, Alton Graviette, Gilbert and Felicia Hawks, Michael and Brenda Craig, Barbara and Russell Danley, Carolyn and Ronald Edwards, Pamela Goins, Amy Gordon, Susan Gregory, Timothy Hall, Ronald Jones, Douglas Lineberry, Marcia Martin, Bobby and Jo Simpson, Karen Stephens, Caroline Moser, Rebecca Tapp, Paul Vaughan, Brenda and Varner Vogler, and Peggie Thomas v.

Oppenheimer & Co.

Inc., Ann Greene and Gordon Morse , filed in Georgia State Court, Fulton County.

Plaintiffs allege that they were all investors in Horizon.

However, all of the plaintiffs allege that they invested in Horizon after John Woods left Oppenheimer’s employ in 2016 and virtually all of the plaintiffs were not Oppenheimer customers.

On September 15, 2023, Oppenheimer filed a motion to transfer the case to the Metro Atlanta Business Case Division, which motion was granted.

On October 31, 2023, Oppenheimer filed a motion to dismiss the complaint, which is pending before the court.

Oppenheimer believes these claims to be without merit and intends to defend itself vigorously against these claims.

On June 30, 2022, the Oppenheimer received a "Wells Notice" from the SEC requesting that Oppenheimer make a written submission to the SEC to explain why Oppenheimer should not be charged with violations of Section 15c2-12 of the Exchange Act, and Rule 15c2-12 thereunder as well as Municipal Securities Rulemaking Board Rules G-17 and G-27 in relation to its sales of municipal notes pursuant to an exemption from continuing disclosure contained in Rule 15c2-12.

On September 13, 2022, the SEC filed a complaint against Oppenheimer in the United States District Court for the Southern District of New York (the “Court") alleging that Oppenheimer violated Section 15B(c)(1) of the Exchange Act and Rule 15c2-12 thereunder as well as Municipal Securities Rulemaking Board Rules G-17 and G-27 for not having fully complied with the exemption from the continuing disclosure obligations under Rule 15c2-12.

The SEC asked the Court to enter an order enjoining Oppenheimer from violating the above referenced rules and requiring it to disgorge

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

approximately $ 1.9 million plus interest.

The Company believes such claim to be without merit and intends to vigorously defend itself against such claim.

The SEC asked the Court to enter an order enjoining Oppenheimer from violating the above-referenced rules and requiring it to disgorge approximately $ 1.9 million plus interest and pay a civil penalty.

On January 30, 2024, Oppenheimer and the SEC reached an agreement in principle to settle the litigation pursuant to which Oppenheimer would pay a civil penalty of $ 1.2 million.

The settlement is subject to Oppenheimer obtaining a waiver of certain statutory disqualifications.

Regulatory requirements

6 unchanged sentences

As of December 31, 2023, Freedom had net capital of $ 4.1 million, which was $ 4.0 million in excess of the $ 100,000 required to be maintained at that date.

As of December 31, 2022, the capital required and held under FCA's Investment Firms' Prudential Regime ("IFPR") for Oppenheimer Europe Ltd.

As of December 31, 2023, the capital required and held under the FCA's Investment Firms' Prudential Regime ("IFPR") for Oppenheimer Europe Ltd.

was as follows:

8 unchanged sentences

Oppenheimer Investments Asia Limited computes its regulatory capital pursuant to the requirements of the Securities and Futures Commission of Hong Kong.

As of December 31, 2022, Oppenheimer Investment Asia Limited was in compliance with its regulatory requirements.

As of December 31, 2023, Oppenheimer Investments Asia Limited was in compliance with its regulatory requirements.

As of December 31, 2023, Oppenheimer Trust is required to maintain minimal capital of $ 4.15 million.

Oppenheimer Trust was in compliance with its capital requirements.

Goodwill and intangibles

The Company's goodwill of $ 137.9 million resides in its PCD reporting unit.

The Company performed its annual test for goodwill impairment as of December 31, 2022 and 2021, which did not result in any impairment charges for either period.

The Company's goodwill of $ 142.2 million resides in its PCD reporting unit ($ 137.9 million) and Corporate/Other reporting unit ($ 4.3 million).

The Company performed its annual test for goodwill impairment for the PCD reporting unit as of December 31, 2023 and 2022, which did not result in any impairment charges for either period.

At each annual goodwill impairment testing date, the PCD reporting unit had a fair value that was substantially in excess of its carrying value.

Intangible Assets

Goodwill within the Corporate/Other reporting unit relates to the Company’s acquisition of BondWave LLC, which closed on December 29, 2023.

Because the valuation of goodwill associated with this transaction was determined on the last business day of 2023, no impairment testing was deemed necessary.

Indefinite intangible assets are comprised of trademarks, trade names and an Internet domain name.

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At each annual intangible assets impairment testing date, the trademarks and trade names had a fair value that was substantially in excess of their carrying value.

OPPENHEIMER HOLDINGS INC.

Notes to Consolidated Financial Statements

Defined-lived intangible assets are comprised of developed technology and customer relationships.

Segment information

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Costs associated with these groups are separately reported in a Corporate/Other category and primarily include compensation and benefits.

The Company also includes activities associated with BondWave, LLC in Corporate/Other.

The table below presents information about the reported revenue and pre-tax income (loss) of the Company for the years ended December 31, 2023, 2022 and 2021.

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Compared sentence by sentence after normalising whitespace, quotation marks, case and digits, so re-formatting and restated figures do not read as changed language. Wording changes appear as one removal and one addition. The current filing and the prior one are authoritative.

What changed 10-K

Item 8. Financial Statements and Supplementary Data