OPPENHEIMER HOLDINGS INC 10-Q

Item 1. FINANCIAL STATEMENTS (UNAUDITED) OPPENHEIMER HOLDINGS INC. CONDENSED CONSOLIDATED BALANCE SHEETS (unaudited) (Expressed in thousands, except number of shares and per share amounts) June 30, 2025 December 31, 2024 ASSETS Cash and cash equivalents $ 37,618 $ 33,150 Deposits with clearing organizations 143,032 98,909 Receivable from brokers, dealers and clearing organizations 290,181 241,478 Receivable from customers, net of allowance for credit losses of $ 169 ($ 175 in 2024) 1,341,550 1,268,866 Income tax receivable 2,663 1,499 Securities owned, including amounts pledged of $ 1,072,282 ($ 1,015,604 in 2024), at fair value 1,256,970 1,108,206 Notes receivable, net 64,316 67,931 Furniture, equipment and leasehold improvements, net of accumulated depreciation of $ 96,605 ($ 92,390 in 2024) 35,470 38,188 Right-of-use lease assets, net of accumulated amortization of $ 130,417 ($ 118,325 in 2024) 127,158 133,821 Corporate-owned life insurance 104,045 98,828 Goodwill 143,607 143,607 Intangible assets 35,376 35,709 Other assets 105,353 112,534 Total assets $ 3,687,339 $ 3,382,726 LIABILITIES AND STOCKHOLDERS' EQUITY Liabilities Drafts payable $ 12,128 $ 21,661 Bank call loans 323,800 252,100 Payable to brokers, dealers and clearing organizations 527,179 253,816 Payable to customers 363,535 357,835 Securities sold under agreements to repurchase 853,123 931,754 Securities sold but not yet purchased, at fair value 203,341 98,892 Accrued compensation 232,728 331,298 Income tax payable 174 3,963 Accounts payable and other liabilities 64,392 65,764 Lease liabilities 165,849 173,320 Deferred tax liabilities, net of deferred tax assets of $ 46,679 ($ 48,640 in 2024) 44,232 41,928 Total liabilities 2,790,481 2,532,331 Commitments and contingencies (Note 13) Stockholders' equity Common stock ($ 0.001 par value per share): Class A: shares authorized: 50,000,000 ; shares issued and outstanding: 10,418,259 and 10,231,736 as of June 30, 2025 and December 31, 2024, respectively Class B: shares authorized, issued and outstanding: 99,665 as of June 30, 2025 and December 31, 2024 10 10 Additional paid-in capital 26,576 29,733 Retained earnings 867,922 819,961 Accumulated other comprehensive income 2,350 691 Total Stockholders' equity 896,858 850,395 Total Liabilities and Stockholders' Equity $ 3,687,339 $ 3,382,726 The accompanying notes are an integral part of these condensed consolidated financial statements. 3 Table of Contents OPPENHEIMER HOLDINGS INC. CONDENSED CONSOLIDATED INCOME STATEMENTS (unaudited) For the Three Months Ended June 30, For the Six Months Ended June 30, (Expressed in thousands, except number of shares and per share amounts) 2025 2024 2025 2024 REVENUE Commissions $ 110,025 $ 97,055 $ 220,903 $ 192,905 Advisory fees 125,628 117,197 254,431 232,044 Investment banking 43,533 29,119 91,156 79,656 Bank deposit sweep income 28,654 34,846 58,729 71,531 Interest 38,017 34,805 74,386 61,571 Principal transactions, net 14,532 10,074 23,507 28,308 Other 12,789 7,493 17,891 17,712 Total revenue 373,178 330,589 741,003 683,727 EXPENSES Compensation and related expenses 239,074 220,727 466,165 442,440 Communications and technology 26,204 24,682 52,386 49,258 Occupancy and equipment costs 15,578 15,516 31,587 31,364 Clearing and exchange fees 7,041 6,780 14,793 12,622 Interest 22,529 21,980 43,925 42,528 Other 30,542 25,039 58,561 52,195 Total expenses 340,968 314,724 667,417 630,407 Pre-tax income 32,210 15,865 73,586 53,320 Income tax provision 10,536 5,599 21,257 17,310 Net income $ 21,674 $ 10,266 $ 52,329 $ 36,010 Net loss attributable to noncontrolling interest, net of tax — — — ( 310 ) Net income attributable to Oppenheimer Holdings Inc. $ 21,674 $ 10,266 $ 52,329 $ 36,320 Earnings per share attributable to Oppenheimer Holdings Inc. Basic $ 2.06 $ 0.99 $ 4.99 $ 3.49 Diluted $ 1.91 $ 0.92 $ 4.63 $ 3.29 Weighted average shares outstanding Basic 10,520,219 10,327,818 10,493,145 10,367,636 Diluted 11,349,049 11,111,903 11,308,979 11,083,422 Period end shares outstanding 10,517,924 10,327,510 10,517,924 10,327,510 The accompanying notes are an integral part of these condensed consolidated financial statements. 4 Table of Contents OPPENHEIMER HOLDINGS INC. CONDENSED CONSOLIDATED STATEMENTS OF COMPREHENSIVE INCOME (unaudited) For the Three Months Ended June 30, For the Six Months Ended June 30, (Expressed in thousands) 2025 2024 2025 2024 Net income $ 21,674 $ 10,266 $ 52,329 $ 36,010 Other comprehensive income (loss), net of tax Currency translation adjustment 2,146 ( 580 ) 1,659 ( 967 ) Comprehensive income $ 23,820 $ 9,686 $ 53,988 $ 35,043 Less net loss attributable to noncontrolling interests — — — ( 310 ) Comprehensive income attributable to Oppenheimer Holdings Inc. $ 23,820 $ 9,686 $ 53,988 $ 35,353 The accompanying notes are an integral part of these condensed consolidated financial statements. 5 Table of Contents OPPENHEIMER HOLDINGS INC. CONDENSED CONSOLIDATED STATEMENTS OF CHANGES IN STOCKHOLDERS' EQUITY AND NONCONTROLLING INTERESTS (unaudited) For the Three Months Ended June 30, For the Six Months Ended June 30, (Expressed in thousands, except per share amount) 2025 2024 2025 2024 Common stock ($ 0.001 par value per share) Balance at beginning of period $ 10 $ 10 $ 10 $ 10 Issuance of Class A non-voting common stock — — — — Repurchase of Class A non-voting common stock for cancellation — — — — Balance at end of period 10 10 10 10 Additional paid-in capital Balance at beginning of period 23,331 20,040 29,733 31,774 Issuance of Class A non-voting common stock 77 171 6,276 8,409 Repurchase of Class A non-voting common stock for cancellation — — ( 90 ) ( 8,384 ) Share-based expense 3,320 3,325 6,778 6,470 Vested employee share plan awards ( 152 ) ( 171 ) ( 16,121 ) ( 15,168 ) Change in redemption value of redeemable noncontrolling interests — — — 264 Balance at end of period 26,576 23,365 26,576 23,365 Retained earnings Balance at beginning of period 848,721 780,946 819,961 756,468 Repurchase of Class A non-voting common stock for cancellation ( 580 ) ( 924 ) ( 580 ) ( 924 ) Net income (1) 21,674 10,266 52,329 36,320 Dividends paid ( 1,893 ) ( 1,549 ) ( 3,788 ) ( 3,125 ) Balance at end of period 867,922 788,739 867,922 788,739 Accumulated other comprehensive income (loss) Balance at beginning of period 204 526 691 914 Currency translation adjustment 2,146 ( 580 ) 1,659 ( 968 ) Balance at end of period 2,350 ( 54 ) 2,350 ( 54 ) Total Oppenheimer Holdings Inc. stockholders' equity $ 896,858 $ 812,060 $ 896,858 $ 812,060 Noncontrolling interest Balance at beginning of period — — — 73 Capital addition to noncontrolling interest — — — 237 Net loss attributable to noncontrolling interest — — — ( 310 ) Balance at end of period — — — — Total stockholders' equity $ 896,858 $ 812,060 $ 896,858 $ 812,060 Dividends paid per share $ 0.18 $ 0.15 $ 0.36 $ 0.30 (1) Attributable to Oppenheimer Holdings Inc. The accompanying notes are an integral part of these condensed consolidated financial statements. OPPENHEIMER HOLDINGS INC. CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS (unaudited) FOR THE SIX MONTHS ENDED JUNE 30, (Expressed in thousands) 2025 2024 Cash flows from operating activities Net income $ 52,329 $ 36,010 Adjustments to reconcile net income to net cash used in operating activities Non-cash items included in net income: Depreciation and amortization of furniture, equipment and leasehold improvements 5,527 5,378 Deferred income taxes 1,874 3,507 Amortization of intangible assets 333 153 Amortization of notes receivable 8,968 8,894 Amortization of debt issuance costs — 109 Provision for credit losses ( 6 ) ( 125 ) Paid-in-kind interest ( 52 ) — Share-based compensation 12,316 14,435 Amortization of right-of-use lease assets 12,901 12,940 Decrease (increase) in operating assets: Deposits with clearing organizations ( 44,123 ) ( 29,709 ) Receivable from brokers, dealers and clearing organizations ( 48,703 ) ( 12,335 ) Receivable from customers ( 72,678 ) ( 101,668 ) Income tax receivable ( 1,164 ) 1,190 Securities purchased under agreements to resell — 1,763 Securities owned ( 148,712 ) ( 247,944 ) Notes receivable ( 5,353 ) ( 9,596 ) Corporate-owned life insurance ( 5,217 ) ( 5,657 ) Other assets 7,291 ( 1,353 ) Increase (decrease) in operating liabilities: Drafts payable ( 9,533 ) 12,760 Payable to brokers, dealers and clearing organizations 273,363 ( 83,664 ) Payable to customers 5,700 ( 43,401 ) Securities sold under agreements to repurchase ( 78,631 ) 182,403 Securities sold but not yet purchased 104,449 145,575 Accrued compensation ( 104,109 ) ( 54,706 ) Income tax payable ( 3,789 ) — Accounts payable and other liabilities ( 14,652 ) ( 29,273 ) Cash used in operating activities ( 51,671 ) ( 194,314 ) Cash flows from investing activities Purchase of furniture, equipment and leasehold improvements ( 2,808 ) ( 1,667 ) Proceeds from the settlement of corporate-owned life insurance 1,549 252 Cash used in investing activities ( 1,259 ) ( 1,415 ) Cash flows from financing activities Cash dividends paid on Class A non-voting and Class B voting common stock ( 3,788 ) ( 3,125 ) Repurchase of Class A non-voting common stock for cancellation ( 671 ) ( 9,309 ) Payments for employee taxes withheld related to vested share-based awards ( 9,843 ) ( 6,758 ) Redemption of redeemable noncontrolling interests — 500 Increase in bank call loans 71,700 218,800 Cash provided by financing activities 57,398 200,108 Net increase in cash and cash equivalents 4,468 4,379 Cash and cash equivalents, beginning of period 33,150 28,835 Cash and cash equivalents, end of period $ 37,618 $ 33,214 Reconciliation of cash and cash equivalents within the condensed consolidated balance sheets: 2025 2024 Cash and cash equivalents $ 37,618 $ 33,214 Total cash and cash equivalents $ 37,618 $ 33,214 Schedule of non-cash financing activities Employee share plan issuance $ 10,396 $ 13,539 Supplemental disclosure of cash flow information Cash paid during the period for interest $ 21,965 $ 41,870 Cash paid during the period for income taxes, net $ 24,195 $ 12,539 The accompanying notes are an integral part of these condensed consolidated financial statements. 6 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 1. Organization Oppenheimer Holdings Inc. ("OPY" or the "Parent") is incorporated under the laws of the State of Delaware. The condensed consolidated financial statements include the accounts of OPY and its consolidated subsidiaries (together, the "Company"). 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 88 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, and Geneva, Switzerland. The principal subsidiaries of OPY are Oppenheimer & Co. Inc. ("Oppenheimer"), a registered broker-dealer in securities and investment adviser under the Investment Advisers Act of 1940; Oppenheimer Asset Management Inc. ("OAM") and its wholly-owned subsidiary, Oppenheimer Investment Management LLC, both registered investment advisers under the Investment Advisers Act of 1940; 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 conducts secondary trading activities related to the purchase and sale of loans and trade claims, primarily on a riskless principal basis; Oppenheimer Europe Ltd., based in the United Kingdom, with offices in the Isle of Jersey, 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. Oppenheimer owns Freedom Investments, Inc. ("Freedom"), a registered broker dealer in securities, which provides discount brokerage services on a limited basis, 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. 2. Summary of significant accounting policies and estimates Basis of Presentation The accompanying condensed consolidated financial statements of the Company have been prepared pursuant to the rules and regulations of the U.S. Securities and Exchange Commission (the "SEC") regarding interim financial reporting. Accordingly, they do not include all of the information and notes required by accounting principles generally accepted in the United States of America ("U.S. GAAP") and should be read in conjunction with the audited consolidated financial statements and notes thereto included in the Company's Annual Report on Form 10-K for the year ended December 31, 2024 (the "Form 10-K"). The accompanying condensed consolidated balance sheet data was derived from the same sources as the audited consolidated financial statements but does not include all disclosures required by U.S. GAAP for annual financial statement purposes. The accompanying condensed consolidated financial statements reflect all adjustments that are, in the opinion of management, necessary for a fair presentation of the financial position, results of operations and cash flows for the interim periods presented. Certain reclassifications have been made to prior periods to place them on a basis comparable with current period presentation. Preparing financial statements requires management to make estimates and assumptions that affect the amounts that are reported in the financial statements and the accompanying disclosures. Although these estimates are based on management's knowledge of current events and actions that the Company may undertake in the future, actual results may differ materially from the estimates. The condensed consolidated results of operations for the three and six months ended June 30, 2025 are not necessarily indicative of the results to be expected for any future interim or annual period. 7 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 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 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. This program acts as an incentive for senior employees to identify attractive private investments for the Company and its clients, and as a retention tool for key employees of the Company. OPI treats its members as partners for tax purposes generally and with respect to the separate Series formed to participate in (i) the incentive fees generated by successful client investments in the Company's Private Market Opportunities program, or (ii) principal investments made by the Company or a portion of the gains thereon, either through the outright purchase of an investment or consideration earned in lieu of an investment banking fee or other transaction fee. Employees who become members of a Series receive a "profit interest", as that term is used in Internal Revenue Service (“IRS”) regulations, and receive an allocation of capital appreciation of the investment held by the particular Series that exceeds a threshold amount established for each Series. Participating employees are also subject to vesting and forfeiture requirements for each Series investment. 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 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. 3. Financial Instruments - Credit Losses Under ASC 326, "Financial Instruments - Credit Losses", the Company can elect to use an approach to measure the allowance for credit losses using the fair value of collateral where the borrower is required to, and reasonably expected to, continually adjust and replenish the amount of collateral securing the instrument to reflect changes in the fair value of such collateral. The Company has elected to use this approach for securities borrowed, margin loans, and reverse repurchase agreements. No material historical losses have been reported on these assets. See note 9 for details. As of June 30, 2025, the Company had $ 64.3 million of notes receivable ($ 67.9 million as of December 31, 2024). 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. These notes generally amortize over a service period of 3 to 9 years from the initial date of the note or based on productivity levels of employees. All such notes are contingent on the employees' continued employment with the Company. The unforgiven portion of the notes becomes due on demand in the event the employee departs during the service period. At that point, any uncollected portion of the notes is reclassified into a defaulted notes category. 8 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) The allowance for uncollectibles is a valuation account that is deducted from the amortized cost basis of the defaulted notes balance to present the net amount expected to be collected. Balances are charged-off against the allowance when management deems the amount to be uncollectible. 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. The expected loss rate is based on historical collection rates of defaulted notes. The expected loss rate is adjusted for changes in environmental and market conditions such as changes in unemployment rates, changes in interest rates and/or other relevant factors. For the three and six months ended June 30, 2025, no adjustments were made to the expected loss rates. The Company will continuously monitor the effect of these factors on the expected loss rate and adjust it as necessary. 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. As of June 30, 2025, the balance of defaulted notes was $ 4.5 million and the allowance for uncollectibles was $ 2.9 million. The allowance for uncollectibles consisted of $ 1.8 million related to defaulted notes balances (five years and older) and $ 1.1 million (under five years). The following table presents the disaggregation of defaulted notes by year of default as of June 30, 2025: (Expressed in thousands) As of June 30, 2025 2025 $ 348 2024 449 2023 750 2022 141 2021 1,033 2020 and prior 1,750 Total $ 4,471 The following table presents activity in the allowance for uncollectibles of defaulted notes for the three and six months ended June 30, 2025 and 2024: (Expressed in thousands) For the Three Months Ended June 30, For the Six Months Ended June 30, 2025 2024 2025 2024 Beginning balance $ 2,983 $ 4,091 $ 2,815 $ 3,869 Additions 128 — 296 129 Reversal — ( 93 ) — — Write-offs ( 255 ) ( 145 ) ( 255 ) ( 145 ) Ending balance $ 2,856 $ 3,853 $ 2,856 $ 3,853 9 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 4. Leases 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 Company 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. In addition, the Company has 88 retail branch offices in the United States as well as offices in London, England, St. Helier, Isle of Jersey, Geneva, Switzerland, Tel Aviv, Israel and Hong Kong, China. The Company is constantly assessing its needs for office space and, on a rolling basis, has many leases that expire in any given year. Substantially all of the leases are held by the Company's subsidiary, Viner Finance Inc., which is a wholly owned subsidiary of the Company. Leases with an initial term of 12 months or less are not recorded on the balance sheet; the Company recognizes lease expense for these leases on a straight-line basis over the lease term. Most leases include an option to renew and the exercise of lease renewal options is at the Company's sole discretion. The Company did not include the renewal options as part of the right of use assets and liabilities. The depreciable life of assets and leasehold improvements is limited by the expected lease term. The Company's lease agreements do not contain any material residual value guarantees or material restrictive covenants. As of June 30, 2025, the Company had right-of-use operating lease assets of $ 127.2 million (net of accumulated amortization of $ 130.4 million) which are comprised of real estate leases of $ 124.4 million (net of accumulated amortization of $ 128.1 million) and equipment leases of $ 2.8 million (net of accumulated amortization of $ 2.3 million). As of June 30, 2025, the Company had operating lease liabilities of $ 165.8 million which are comprised of real estate lease liabilities of $ 163.1 million and equipment lease liabilities of $ 2.8 million. The Company had no finance leases as of June 30, 2025. As most of the Company's leases do not provide an implicit rate, the Company uses the incremental borrowing rate based on the information available at commencement date in determining the present value of lease payments. The following table presents the weighted average lease term and weighted average discount rate for the Company's operating leases as of June 30, 2025 and December 31, 2024, respectively: As of June 30, 2025 December 31, 2024 Weighted average remaining lease term (in years) 5.84 6.08 Weighted average discount rate 7.40 % 7.50 % The following table presents operating lease costs recognized for the three and six months ended June 30, 2025 and June 30, 2024, respectively, which are included in occupancy and equipment costs on the condensed consolidated income statements: (Expressed in thousands) For the Three Months Ended June 30, For the Six Months Ended June 30, 2025 2024 2025 2024 Operating lease costs: Real estate leases - Right-of-use lease asset amortization $ 6,094 $ 6,031 $ 12,051 $ 12,077 Real estate leases - Interest expense 3,019 3,228 6,148 6,551 Equipment leases - Right-of-use lease asset amortization 425 432 849 863 Equipment leases - Interest expense 48 44 93 90 10 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) The maturities of lease liabilities as of June 30, 2025 and December 31, 2024 are as follows: (Expressed in thousands) As of June 30, 2025 December 31, 2024 2025 $ 21,919 $ 42,466 2026 42,459 40,596 2027 39,686 38,151 2028 25,744 24,794 2029 19,594 18,816 After 2030 56,135 52,472 Total lease payments $ 205,537 $ 217,295 Less interest ( 39,688 ) ( 43,975 ) Present value of lease liabilities $ 165,849 $ 173,320 As of June 30, 2025, the Company had $ 1.9 million of additional real estate operating leases that have not yet commenced ($ 6.9 million as of December 31, 2024). 5. Revenue from contracts with customers Revenue from contracts with customers is recognized when, or as, the Company satisfies its performance obligations by transferring the promised goods or services to customers. A good or service is transferred to a customer when, or as, the customer obtains control of that good or service. A performance obligation may be satisfied over time or at a point in time. Revenue from a performance obligation satisfied over time is recognized by measuring the Company's progress in satisfying the performance obligation in a manner that depicts the transfer of the goods or services to the customer. Revenue from a performance obligation satisfied at a point in time is recognized at the point in time that the Company determines the customer obtains control over the promised good or service. The amount of revenue recognized reflects the consideration to which the Company expects to be entitled in exchange for those promised goods or services (i.e., the "transaction price"). In determining the transaction price, the Company considers multiple factors, including the effects of variable consideration. Variable consideration is included in the transaction price only to the extent it is probable that a significant reversal in the amount of cumulative revenue recognized will not occur when the uncertainties with respect to the amount are resolved. In determining when to include variable consideration in the transaction price, the Company considers the range of possible outcomes, the predictive value of its past experiences, the time period during which uncertainties are expected to be resolved and the amount of consideration that is susceptible to factors outside of the Company's influence, such as market volatility or the judgment and actions of third parties. The Company earns revenue from contracts with customers and other sources (principal transactions, interest and other). The following provides detailed information on the recognition of the Company's revenue from contracts with customers: Commissions Commissions from Sales and Trading — The Company earns commission revenue by executing, settling and clearing transactions with clients primarily in exchange-traded and over-the-counter corporate equity and debt securities, money market instruments and exchange-traded options and futures contracts. A substantial portion of the Company's revenue is derived from commissions from private clients through accounts with transaction-based pricing. Trade execution and clearing services, when provided together, represent a single performance obligation as the services are not separately identifiable in the context of the contract. Commission revenue associated with combined trade execution and clearing services, as well as trade execution services on a standalone basis, is recognized at a point in time on trade date when the performance obligation is satisfied. Commission revenue is generally paid on settlement date, which is generally one business day after trade date. The Company records a receivable on the trade date and receives a payment on the settlement date. 11 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) Mutual Fund Income — The Company earns mutual fund income for sales and distribution of mutual fund shares, which consists of a fixed fee amount and a variable amount. The Company recognizes mutual fund income at a point in time on the trade date when the performance obligation is satisfied which is when the mutual fund interest is sold to the investor. The ongoing distribution fees for distributing investment products from mutual fund companies are generally considered variable consideration because they are based on the value of AUM and are uncertain on trade date. The Company recognizes distribution fees over the investment period as the amounts become known and the portion recognized in the current period may relate to distribution services performed in prior periods. Mutual fund income is generally received within 90 days. Advisory Fees The Company earns management and performance (or incentive) fees in connection with the advisory and asset management services it provides to various types of funds, asset-based programs and investment vehicles through its subsidiaries. Management fees are generally based on the account value at the valuation date per the respective asset management agreements and are recognized over time as the customer receives the benefits of the services evenly throughout the term of the contract. Performance fees are recognized when the return on client AUM exceeds a specified benchmark return or other performance targets over a 12-month measurement period are met. Performance fees are considered variable as they are subject to fluctuation and/or are contingent on a future event over the measurement period and are not subject to adjustment once the measurement period ends. Such fees are computed as of the fund's year-end when the measurement period ends and generally are recorded as earned in the fourth quarter of the Company's fiscal year. Both management and performance fees are generally received within 90 days. Investment Banking The Company earns underwriting revenue by providing capital raising solutions for corporate clients through initial public offerings, follow-on offerings, equity-linked offerings, private investments in public entities, and private placements. Underwriting revenue is recognized at a point in time on trade date, as the client obtains the control and benefit of the capital markets offering at that time. These fees are generally received within 90 days after the transactions are completed. Transaction-related expenses, primarily consisting of legal, travel and other costs directly associated with the transaction, are deferred and recognized in the same period as the related investment banking transaction revenue. Underwriting revenue and related expenses are presented gross on the consolidated income statements. Revenue from financial advisory services includes fees generated in connection with mergers, acquisitions and restructuring transactions. Such revenue and fees are primarily recorded at a point in time when services for the performance obligations have been completed and income is reasonably determinable, generally as set forth under the terms of the engagement. Payment for advisory services is generally due upon a completion of the transaction or milestone. Retainer fees and fees earned from certain advisory services are recognized ratably over the service period as the customer receives the benefit of the services throughout the term of the contracts, and such fees are collected based on the terms of the contracts. Bank Deposit Sweep Income Bank deposit sweep income consists of revenue earned from the FDIC-insured bank deposit program. Under this program, client funds are swept into deposit accounts at participating banks and are eligible for FDIC deposit insurance up to FDIC standard maximum deposit insurance amounts. Fees are earned over time and are generally received within 30 days. 12 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) Disaggregation of Revenue The following presents the Company's revenue from contracts with customers disaggregated by major business activity and other sources of revenue for the three and six months ended June 30, 2025 and 2024: (Expressed in thousands) For the Three Months Ended June 30, 2025 Reportable Segments Wealth Management Capital Markets Corporate/Other Total Revenue from contracts with customers: Commissions from sales and trading $ 47,203 $ 55,217 $ 13 $ 102,433 Mutual fund and insurance income 7,585 1 6 7,592 Advisory fees 125,610 — 18 125,628 Investment banking - capital markets 2,758 18,288 — 21,046 Investment banking - advisory — 22,487 — 22,487 Bank deposit sweep income 28,654 — — 28,654 Other 3,620 547 1,398 5,565 Total revenue from contracts with customers 215,430 96,540 1,435 313,405 Other sources of revenue: Interest 21,943 14,252 1,822 38,017 Principal transactions, net 1,973 12,051 508 14,532 Other 7,075 138 11 7,224 Total other sources of revenue 30,991 26,441 2,341 59,773 Total revenue $ 246,421 $ 122,981 $ 3,776 $ 373,178 (Expressed in thousands) For the Three Months Ended June 30, 2024 Reportable Segments Wealth Management Capital Markets Corporate/Other Total Revenue from contracts with customers: Commissions from sales and trading $ 44,766 $ 44,174 $ 3 $ 88,943 Mutual fund and insurance income 8,106 1 5 8,112 Advisory fees 117,188 — 9 117,197 Investment banking - capital markets 2,807 14,022 ( 1 ) 16,828 Investment banking - advisory — 12,291 — 12,291 Bank deposit sweep income 34,847 — ( 1 ) 34,846 Other 3,167 580 1,942 5,689 Total revenue from contracts with customers 210,881 71,068 1,957 283,906 Other sources of revenue: Interest 21,626 11,410 1,769 34,805 Principal transactions, net 376 9,566 132 10,074 Other 1,643 97 64 1,804 Total other sources of revenue 23,645 21,073 1,965 46,683 Total revenue $ 234,526 $ 92,141 $ 3,922 $ 330,589 13 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) (Expressed in thousands) For the Six Months Ended June 30, 2025 Reportable Segments Wealth Management Capital Markets Corporate/Other Total Revenue from contracts with customers: Commissions from sales and trading $ 95,970 $ 109,165 $ 25 $ 205,160 Mutual fund and insurance income 15,729 2 12 15,743 Advisory fees 254,402 — 29 254,431 Investment banking - capital markets 5,720 36,987 — 42,707 Investment banking - advisory — 48,449 — 48,449 Bank deposit sweep income 58,729 — — 58,729 Other 7,969 1,655 2,711 12,335 Total revenue from contracts with customers 438,519 196,258 2,777 637,554 Other sources of revenue: Interest 43,428 27,706 3,252 74,386 Principal transactions, net 1,386 21,846 275 23,507 Other 5,074 432 50 5,556 Total other sources of revenue 49,888 49,984 3,577 103,449 Total revenue $ 488,407 $ 246,242 $ 6,354 $ 741,003 (Expressed in thousands) For the Six Months Ended June 30, 2024 Reportable Segments Wealth Management Capital Markets Corporate/Other Total Revenue from contracts with customers: Commissions from sales and trading $ 89,696 $ 87,219 $ 8 $ 176,923 Mutual fund and insurance income 15,970 2 10 15,982 Advisory fees 232,024 — 20 232,044 Investment banking - capital markets 5,828 29,649 ( 1 ) 35,476 Investment banking - advisory 21 44,159 — 44,180 Bank deposit sweep income 71,532 — ( 1 ) 71,531 Other 6,583 900 2,922 10,405 Total revenue from contracts with customers 421,654 161,929 2,958 586,541 Other sources of revenue: Interest 41,822 15,713 4,036 61,571 Principal transactions, net 2,112 26,299 ( 103 ) 28,308 Other 6,899 283 125 7,307 Total other sources of revenue 50,833 42,295 4,058 97,186 Total revenue $ 472,487 $ 204,224 $ 7,016 $ 683,727 14 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) Contract Assets and Liabilities The timing of the Company's revenue recognition may differ from the timing of payment by its customers. The Company records contract assets when payment is due from a client conditioned on future performance or the occurrence of other events. Alternatively, when payment precedes the provision of the related services, the Company records deferred revenue until the performance obligations are satisfied. The Company had receivables related to revenue from contracts with customers of $ 45.3 million and $ 46.2 million at June 30, 2025 and December 31, 2024, respectively. The Company had no significant impairments related to these receivables during the three and six months ended June 30, 2025. Deferred revenue relates to IRA fees received annually in advance on customers' IRA accounts managed by the Company, software license fees received upfront from customers and retainer fees and other fees earned from certain advisory transactions where the performance obligations have not yet been satisfied. Total deferred revenue was $ 3.3 million and $ 0.9 million at June 30, 2025 and December 31, 2024, 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 June 30, 2025 December 31, 2024 Receivables Commission (1) $ 8,918 $ 4,408 Mutual fund and insurance income (2) 5,575 5,838 Advisory fees (3) 5,596 11,271 Bank deposit sweep income (4) 4,348 4,748 Investment banking fees (5) 13,428 14,798 Other 7,387 5,124 Total receivables $ 45,252 $ 46,187 Deferred revenue (payables): Investment Banking fees (6) $ 184 $ 28 Software license fees (7) 1,960 902 IRA fees (8) 1,200 — $ 3,344 $ 930 (1) Commissions earned but not yet received. (2) Mutual fund and insurance income earned but not yet received. (3) Management and performance fees earned but not yet received. (4) Fees earned from FDIC-insured bank deposit program but not yet received. (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. (7) Software license fees received upfront from customers and recognized ratably over the contract period (8) Fees received in advance on an annual basis. 15 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 6. 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. 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. Earnings per share have been calculated as follows: (Expressed in thousands, except number of shares and per share amounts) For the Three Months Ended June 30, For the Six Months Ended June 30, 2025 2024 2025 2024 Basic weighted average number of shares outstanding 10,520,219 10,327,818 10,493,145 10,367,636 Net dilutive effect of share-based awards, treasury stock method (1) 828,830 784,085 815,834 715,786 Diluted weighted average number of shares outstanding 11,349,049 11,111,903 11,308,979 11,083,422 Net income attributable to Oppenheimer Holdings Inc. $ 21,674 $ 10,266 $ 52,329 $ 36,320 Earnings per share attributable to Oppenheimer Holdings Inc. Basic $ 2.06 $ 0.99 $ 4.99 $ 3.49 Diluted $ 1.91 $ 0.92 $ 4.63 $ 3.29 (1) For the three months ended June 30, 2025, the diluted net income per share computation did not include the anti-dilutive effect of 199,850 shares of Class A Stock granted under share-based compensation arrangements. For the six months ended June 30, 2025, the diluted net income per share computation did not include the anti-dilutive effect of 202,475 shares of Class A Stock granted under share-based compensation arrangements. For the three months ended June 30, 2024, there were no shares of Class A Stock with an anti-dilutive effect granted under share-based compensation arrangements. For the six months ended June 30, 2024, the diluted net income per share computation did not include the anti-dilutive effect of 1,000 shares of Class A Stock granted under share-based compensation arrangements. 7. Receivable from and payable to brokers, dealers and clearing organizations (Expressed in thousands) As of June 30, 2025 December 31, 2024 Receivable from brokers, dealers and clearing organizations consisting of: Securities borrowed $ 139,852 $ 137,177 Receivable from brokers 53,263 59,487 Securities failed to deliver 39,665 8,459 Clearing organizations and other (1) 57,401 36,355 Total $ 290,181 $ 241,478 Payable to brokers, dealers and clearing organizations consisting of: Securities loaned $ 404,916 $ 235,498 Securities failed to receive 20,751 14,757 Payable to brokers 3,099 607 Clearing organizations and other (2) 98,413 2,954 Total $ 527,179 $ 253,816 (1) As of December 31, 2024, approximately $ 15.4 million of this balance represents a receivable for trades executed, but not yet settled. (2) As of June 30, 2025, approximately $ 89.4 million of this balance represents a payable for trades executed, but not yet settled. 16 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 8. Fair value measurements Securities owned, securities sold but not yet purchased, investments, derivative contracts and certain loans are carried at fair value with changes in fair value recognized in earnings each period. Fair value is defined as the price that would be received to sell an asset, or paid to transfer a liability, in an orderly transaction between market participants at the measurement date. A description of the valuation techniques applied and inputs used in measuring the fair value of the Company’s financial instruments, as well as the general classification of such instruments pursuant to the valuation hierarchy, are as follows: Securities The Company determines the fair value of securities (both long and short) primarily based on pricing sources with reasonable levels of price transparency. Where unadjusted quoted prices for identical assets or liabilities are available in an active market, we classify the securities within Level 1 of the valuation hierarchy. Level 1 securities include U.S. Treasury securities, money market funds and corporate equities. If quoted market prices are unavailable, fair values are generally determined using pricing models which incorporate market observable inputs, such as benchmark yields, recently executed transaction prices, issuer spreads, reported trades, bids, offers and other reference data. Examples of such instruments, which are typically classified within Level 2 of the valuation hierarchy, include U.S. Agency securities, sovereign obligations, corporate debt and other obligations, mortgage and other asset-backed securities, municipal obligations, money market funds and convertible bonds. In limited situations where there is reduced activity or less observability around inputs to the valuation, we classify those securities in Level 3 of the valuation hierarchy. The Company has valued the auction rate 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. As of June 30, 2025 and December 31, 2024, the Company had $ 128,000 and $ 2.7 million, respectively, of auction rate securities in Level 3 assets. Additionally, the Company has valued a convertible note using a discount cash flow model and warrants using a Black-Scholes option pricing model and categorized them in Level 3 of the fair value hierarchy due to the models' use of unobservable inputs. As of June 30, 2025, the Company had $ 1.9 million and $ 1.2 million of convertible note and warrants, respectively, in Level 3 assets. Derivative financial instruments The Company classifies exchange-traded derivative financial instruments such as futures contracts in Level 1 of the valuation hierarchy. Some of our derivative positions, such as to-be-announced securities, are valued using models that use observable market parameters, and we classify them in Level 2 of the valuation hierarchy. Loans The fair value of loans is estimated using recently executed transactions and current price quotations, which are usually observable. In rare occurrences when observable pricing information is not available, fair value is generally determined based on cash flow models using discounted cash flow models, competitor comparable data and other valuation metrics. Other The Company owns an equity method 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. The Company determined the fair value of the investment based on an implied market-multiple approach and observable market data, including comparable company transactions. As of June 30, 2025 and December 31, 2024, the fair value of the investment was $ 6.3 million and $ 5.9 million, respectively, and was categorized in Level 2 of the fair value hierarchy. Trade claims are categorized in Level 3 of the fair value hierarchy due to the illiquid nature of the claims and the period of time since the executed prices. As of June 30, 2025, the Company had no trade claims. 17 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) Investments 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 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. The following table provides information about the Company's investments in Company-sponsored funds as of June 30, 2025: (Expressed in thousands) Fair Value Unfunded Commitments Redemption Frequency Redemption Notice Period Hedge funds (1) $ 262 $ — Quarterly - Annually 30 - 120 Days Private equity funds (2) 5,302 790 N/A N/A $ 5,564 $ 790 (1) Hedge funds represent investments in credit driven strategies. (2) Private equity funds includes portfolios focused on technology, infrastructure, real estate, natural resources and specific co-investment opportunities. The following table provides information about the Company's investments in Company-sponsored funds as of December 31, 2024: (Expressed in thousands) Fair Value Unfunded Commitments Redemption Frequency Redemption Notice Period Hedge funds (1) $ 283 $ — Quarterly - Annually 30 - 120 Days Private equity funds (2) 5,090 1,314 N/A N/A $ 5,373 $ 1,314 (1) Hedge funds represent investments in credit driven strategies. (2) Private equity funds includes portfolios focused on technology, infrastructure, real estate, natural resources and specific co-investment opportunities. 18 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) Assets and Liabilities Measured at Fair Value The Company's assets and liabilities, recorded at fair value on a recurring basis as of June 30, 2025 and December 31, 2024, have been categorized based upon the above fair value hierarchy as follows: Assets and liabilities measured at fair value on a recurring basis as of June 30, 2025 : (Expressed in thousands) Fair Value Measurements as of June 30, 2025 Level 1 Level 2 Level 3 Total Assets Deposits with clearing organizations $ 27,683 $ — $ — $ 27,683 Securities owned: U.S. Treasury securities 1,053,781 — — 1,053,781 U.S. Agency securities — 3,408 — 3,408 Sovereign obligations — 1,230 — 1,230 Corporate debt and other obligations — 35,094 1,862 36,956 Mortgage and other asset-backed securities — 7,933 — 7,933 Municipal obligations — 92,617 — 92,617 Convertible bonds — 23,135 — 23,135 Corporate equities 29,654 — 1,190 30,844 Money markets 6,500 438 — 6,938 Auction rate securities — — 128 128 Securities owned, at fair value 1,089,935 163,855 3,180 1,256,970 Investments (1) — 17,771 — 17,771 Loans (1) — 830 — 830 Derivative contracts: TBAs — 100 — 100 Derivative contracts, total — 100 — 100 Total $ 1,117,618 $ 182,556 $ 3,180 $ 1,303,354 Liabilities Securities sold but not yet purchased: U.S. Treasury securities $ 152,538 $ — $ — $ 152,538 U.S. Agency securities — 1 — 1 Sovereign obligations — 9,159 — 9,159 Corporate debt and other obligations — 14,779 — 14,779 Convertible bonds — 16,194 — 16,194 Corporate equities 10,670 — — 10,670 Securities sold but not yet purchased, at fair value 163,208 40,133 — 203,341 Derivative contracts: Futures (2) 846 — — 846 TBAs — 94 — 94 Derivative contracts, total 846 94 — 940 Total $ 164,054 $ 40,227 $ — $ 204,281 (1) Included in other assets on the consolidated balance sheet. (2) Included in receivable/payable from/to brokers, dealers and clearing organizations on the consolidated balance sheet. 19 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) Assets and liabilities measured at fair value on a recurring basis as of December 31, 2024: (Expressed in thousands) Fair Value Measurements as of December 31, 2024 Level 1 Level 2 Level 3 Total Assets Deposits with clearing organizations $ 28,071 $ — $ — $ 28,071 Securities owned: U.S. Treasury securities 995,420 — — 995,420 U.S. Agency securities — 3,691 — 3,691 Corporate debt and other obligations — 9,423 — 9,423 Mortgage and other asset-backed securities — 8,954 — 8,954 Municipal obligations — 34,704 — 34,704 Convertible bonds — 21,938 — 21,938 Corporate equities 23,873 — — 23,873 Money markets 7,551 — — 7,551 Auction rate securities — — 2,652 2,652 Securities owned, at fair value 1,026,844 78,710 2,652 1,108,206 Investments (1) 978 17,005 — 17,983 Trade claims (1) — — 2,684 2,684 Loans (1) — 432 — 432 Total $ 1,055,893 $ 96,147 $ 5,336 $ 1,157,376 Liabilities Securities sold but not yet purchased: U.S. Treasury securities $ 82,767 $ — $ — $ 82,767 U.S. Agency securities — 4 — 4 Corporate debt and other obligations — 11 — 11 Convertible bonds — 4,998 — 4,998 Corporate equities 11,112 — — 11,112 Securities sold but not yet purchased, at fair value 93,879 5,013 — 98,892 Derivative contracts: Futures (2) 1,071 — — 1,071 Derivative contracts, total 1,071 — — 1,071 Total $ 94,950 $ 5,013 $ — $ 99,963 (1) Included in other assets on the consolidated balance sheet. (2) Included in receivable/payable to brokers, dealers and clearing organizations on the consolidated balance sheet. 20 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) The following tables present changes in Level 3 assets and liabilities measured at fair value on a recurring basis for the three and six months ended June 30, 2025 and 2024: (Expressed in thousands) Level 3 Assets and Liabilities For the Three Months Ended June 30, 2025 Total Realized Beginning and Unrealized Purchases Sales and Transfers Ending Balance Gain (2) and Issuances Settlements In (Out) Balance Assets Corporate equities $ — $ 20 $ 1,170 $ — $ — $ 1,190 Corporate debt and other obligations — 32 1,830 — — 1,862 Auction rate securities (1) 128 — — — — 128 Trade claims 3,218 957 — ( 4,175 ) — — (1) Represents auction rate securities that failed in the auction rate market. (2) Included in principal transactions in the consolidated income statement. (Expressed in thousands) Level 3 Assets and Liabilities For the Three Months Ended June 30, 2024 Total Realized Beginning and Unrealized Purchases Sales and Transfers Ending Balance Gain (2) and Issuances Settlements In (Out) Balance Assets Auction rate securities (1) $ 2,713 $ — $ — $ — $ — $ 2,713 (1) Represents auction rate securities that failed in the auction rate market. (2) Included in principal transactions in the consolidated income statement. (Expressed in thousands) Level 3 Assets and Liabilities For the Six Months Ended June 30, 2025 Total Realized Beginning and Unrealized Purchases Sales and Transfers Ending Balance Gain (2) and Issuances Settlements In (Out) Balance Assets Corporate equities $ — 20 1,170 $ — $ — $ 1,190 Corporate debt and other obligations — 32 1,830 — — 1,862 Auction rate securities (1) 2,652 206 — ( 2,730 ) — 128 Trade claims 2,684 957 534 ( 4,175 ) — — (1) Represents auction rate securities that failed in the auction rate market. (2) Included in principal transactions in the consolidated income statement. (Expressed in thousands) Level 3 Assets and Liabilities For the Six Months Ended June 30, 2024 Total Realized Beginning and Unrealized Purchases Sales and Transfers Ending Balance Gain (2) and Issuances Settlements In (Out) Balance Assets Auction rate securities (1) $ 2,713 $ — $ — $ — $ — $ 2,713 (1) Represents auction rate securities that failed in the auction rate market. (2) Included in principal transactions in the consolidated income statement. 21 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) Financial Instruments Not Measured at Fair Value The table below presents the carrying value, fair value and fair value hierarchy category of certain financial instruments that are not measured at fair value on the consolidated balance sheets. The table below excludes non-financial assets and liabilities (e.g., furniture, equipment and leasehold improvements and accrued compensation). The carrying value of financial instruments not measured at fair value categorized in the fair value hierarchy as Level 1 or Level 2 (e.g., cash and receivables from customers) approximates fair value because of the relatively short-term nature of the underlying assets. Assets and liabilities not measured at fair value as of June 30, 2025: (Expressed in thousands) Fair Value Measurement: Assets Carrying Value Level 1 Level 2 Level 3 Total Cash and cash equivalents $ 37,618 $ 37,618 $ — $ — $ 37,618 Deposits with clearing organizations 115,349 115,349 — — 115,349 Receivable from brokers, dealers and clearing organizations: Securities borrowed 139,852 — 139,852 — 139,852 Receivables from brokers 53,263 — 53,263 — 53,263 Securities failed to deliver 39,665 — 39,665 — 39,665 Clearing organizations and other 57,401 — 57,401 — 57,401 290,181 — 290,181 — 290,181 Receivable from customers 1,341,550 — 1,341,550 — 1,341,550 Notes receivable, net 64,316 — 64,316 — 64,316 Corporate-owned life insurance 104,045 — 104,045 — 104,045 Investments (1) 2,016 — 2,016 — 2,016 (1) Included within other assets on the consolidated balance sheet. (Expressed in thousands) Fair Value Measurement: Liabilities Carrying Value Level 1 Level 2 Level 3 Total Drafts payable $ 12,128 $ 12,128 $ — $ — $ 12,128 Bank call loans 323,800 — 323,800 — 323,800 Payables to brokers, dealers and clearing organizations: Securities loaned 404,916 — 404,916 — 404,916 Payable to brokers 3,099 — 3,099 — 3,099 Securities failed to receive 20,751 — 20,751 — 20,751 Clearing organization and other 97,353 — 97,353 — 97,353 526,119 — 526,119 — 526,119 Payables to customers 363,535 — 363,535 — 363,535 Securities sold under agreements to repurchase 853,123 — 853,123 — 853,123 22 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) Assets and liabilities not measured at fair value as of December 31, 2024: (Expressed in thousands) Fair Value Measurement: Assets Carrying Value Level 1 Level 2 Level 3 Total Cash and cash equivalents $ 33,150 $ 33,150 $ — $ — $ 33,150 Deposits with clearing organization 70,838 70,838 — — 70,838 Receivable from brokers, dealers and clearing organizations: Securities borrowed 137,177 — 137,177 — 137,177 Receivables from brokers 59,487 — 59,487 — 59,487 Securities failed to deliver 8,459 — 8,459 — 8,459 Clearing organizations and other 36,355 — 36,355 — 36,355 241,478 — 241,478 — 241,478 Receivable from customers 1,268,866 — 1,268,866 — 1,268,866 Notes receivable, net 67,931 — 67,931 — 67,931 Corporate-owned life insurance 98,828 — 98,828 — 98,828 Investments (1) 1,634 — 1,634 — 1,634 (1) Included within other assets on the consolidated balance sheet. (Expressed in thousands) Fair Value Measurement: Liabilities Carrying Value Level 1 Level 2 Level 3 Total Drafts payable $ 21,661 $ 21,661 $ — $ — $ 21,661 Bank call loans 252,100 — 252,100 — 252,100 Payables to brokers, dealers and clearing organizations: Securities loaned 235,498 — 235,498 — 235,498 Payable to brokers 607 — 607 — 607 Securities failed to receive 14,757 — 14,757 — 14,757 Clearing organizations and other 1,883 — 1,883 — 1,883 252,745 — 252,745 — 252,745 Payables to customers 357,835 — 357,835 — 357,835 Securities sold under agreements to repurchase 931,754 — 931,754 — 931,754 Derivative Instruments and Hedging Activities The Company transacts, on a limited basis, in exchange traded and over-the-counter derivatives for both asset and liability management as well as for trading and investment purposes. Risks managed using derivative instruments include interest rate risk and, to a lesser extent, foreign exchange risk. All derivative instruments are measured at fair value and are recognized as either assets or liabilities on the consolidated balance sheet. Foreign exchange hedges From time to time, the Company also utilizes forward and options contracts to hedge the foreign currency risk associated with compensation obligations to Oppenheimer Israel (OPCO) Ltd. employees denominated in New Israeli Shekel ("NIS"). Such hedges have not been designated as accounting hedges. 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. 23 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) Derivatives used for trading and investment purposes Futures contracts represent commitments to purchase or sell securities or other commodities at a future date and at a specified price. Market risk exists with respect to these instruments. Notional or contractual amounts are used to express the volume of these transactions and do not represent the amounts potentially subject to market risk. The Company uses futures contracts, including U.S. Treasury Notes, federal funds, general collateral futures and Eurodollar contracts primarily as an economic hedge of interest rate risk associated with government trading activities. Unrealized gains and losses on futures contracts are recorded on the consolidated balance sheet in payable to or receivable from brokers, dealers and clearing organizations and in the consolidated income statement as principal transactions revenue, net. To-be-announced securities The Company also transacts in pass-through mortgage-backed securities eligible to be sold in the TBA market as economic hedges against mortgage-backed securities that it owns or has sold but not yet purchased. TBAs provide for the forward or delayed delivery of the underlying instrument with settlement up to 180 days. The contractual or notional amounts related to these financial instruments reflect the volume of activity and do not reflect the amounts at risk. 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. The notional amounts and fair values of the Company's derivatives as of June 30, 2025 and December 31, 2024 by product were as follows: (Expressed in thousands) Fair Value of Derivative Instruments as of June 30, 2025 Description Notional Fair Value Assets: Derivatives not designated as hedging instruments (1) Other contracts TBAs $ 12,100 $ 94 Commodity contracts Futures 500,000 — $ 512,100 $ 94 Liabilities: Derivatives not designated as hedging instruments (1) Commodity contracts Futures $ 12,370,000 $ 846 Other contracts TBAs 12,100 100 $ 12,382,100 $ 946 (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. 24 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) (Expressed in thousands) Fair Value of Derivative Instruments as of December 31, 2024 Description Notional Fair Value Assets: Derivatives not designated as hedging instruments (1) Other contracts TBAs $ 360 $ — $ 360 $ — Liabilities: Derivatives not designated as hedging instruments (1) Commodity contracts Futures $ 11,475,000 $ 1,071 Other contracts TBAs 360 — $ 11,475,360 $ 1,071 (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. 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 three and six months ended June 30, 2025 and 2024: (Expressed in thousands) The Effect of Derivative Instruments in the Income Statement For the Three Months Ended June 30, 2025 Recognized in Income on Derivatives (pre-tax) Types Description Location Net Gain (Loss) Commodity contracts Futures Principal transactions revenue, net $ 393 Other contracts TBAs Principal transactions revenue, net 16 $ 409 (Expressed in thousands) The Effect of Derivative Instruments in the Income Statement For the Three Months Ended June 30, 2024 Recognized in Income on Derivatives (pre-tax) Types Description Location Net Gain (Loss) Commodity contracts Futures Principal transactions revenue, net $ 1,184 Other contracts Foreign exchange forward contracts Other revenue/(Compensation and related expenses) ( 24 ) Other contracts TBAs Principal transactions revenue, net 2 $ 1,162 25 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) (Expressed in thousands) The Effect of Derivative Instruments in the Income Statement For the Six Months Ended June 30, 2025 Recognized in Income on Derivatives (pre-tax) Types Description Location Net Gain (Loss) Commodity contracts Futures Principal transactions revenue, net $ ( 745 ) Other contracts TBAs Principal transactions revenue, net 16 $ ( 729 ) (Expressed in thousands) The Effect of Derivative Instruments in the Income Statement For the Six Months Ended June 30, 2024 Recognized in Income on Derivatives (pre-tax) Types Description Location Net Gain (Loss) Commodity contracts Futures Principal transactions revenue, net $ 4,436 Other contracts Foreign exchange forward contracts Other revenue/(Compensation and related expenses) ( 24 ) Other contracts TBAs Principal transactions revenue, net 3 $ 4,415 26 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 9. Collateralized transactions The Company enters into collateralized borrowing and lending transactions in order to meet customers' needs and earn interest rate spreads, obtain securities for settlement and finance trading inventory positions. Under these transactions, the Company either receives or provides collateral, including U.S. Government and Agency, asset-backed, corporate debt, equity, and non-U.S. Government and Agency securities. The Company obtains short-term borrowings primarily through bank call loans. Bank call loans are generally payable on demand and bear interest at various rates. As of June 30, 2025, the outstanding balance of bank call loans was $ 323.8 million ($ 252.1 million as of December 31, 2024). As of June 30, 2025, such loans with commercial banks were collateralized by the Company's securities and customer securities with market values of approximately $ 41.3 million and $ 320 million, respectively. As of June 30, 2025, the Company had approximately $ 1.8 billion of customer securities under customer margin loans that are available to be pledged, of which the Company has re-pledged approximately $ 339.1 million under securities loan agreements. As of June 30, 2025, the Company had pledged $ 182.2 million of customer securities directly with the Options Clearing Corporation to secure obligations and margin requirements under option contracts written by customers. As of June 30, 2025, the Company had no outstanding letters of credit. The Company enters into reverse repurchase agreements, repurchase agreements, securities borrowed and securities loaned transactions to, among other things, acquire securities to cover short positions and settle other securities obligations, to accommodate customers' needs and to finance the Company's inventory positions. Except as described below, repurchase and reverse repurchase agreements, principally involving U.S. Government and Agency securities, are carried at amounts at which the securities subsequently will be resold or reacquired as specified in the respective agreements and include accrued interest. 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. 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 June 30, 2025: (Expressed in thousands) Overnight and Open Repurchase agreements: U.S. Treasury securities $ 1,046,021 Securities loaned: Corporate equities 404,916 Gross amount of recognized liabilities for repurchase agreements and securities loaned $ 1,450,937 27 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 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 June 30, 2025 and December 31, 2024: As of June 30, 2025 (Expressed in thousands) Gross Amounts Not Offset on the Balance Sheet Gross Amounts of Recognized Assets Gross Amounts Offset on the Balance Sheet Net Amounts of Assets Presented on the Balance Sheet Financial Instruments Cash Collateral Received Net Amount Reverse repurchase agreements $ 192,898 $ ( 192,898 ) $ — $ — $ — $ — Securities borrowed (1) 139,852 — 139,852 ( 136,622 ) — 3,230 Total $ 332,750 $ ( 192,898 ) $ 139,852 $ ( 136,622 ) $ — $ 3,230 (1) Included in receivable from brokers, dealers and clearing organizations on the consolidated balance sheet. (Expressed in thousands) Gross Amounts Not Offset on the Balance Sheet Gross Amounts of Recognized Liabilities Gross Amounts Offset on the Balance Sheet Net Amounts of Liabilities Presented on the Balance Sheet Financial Instruments Cash Collateral Pledged Net Amount Repurchase agreements $ 1,046,021 $ ( 192,898 ) $ 853,123 $ ( 853,123 ) $ — $ — Securities loaned (2) 404,916 — 404,916 ( 393,219 ) — 11,697 Total $ 1,450,937 $ ( 192,898 ) $ 1,258,039 $ ( 1,246,342 ) $ — $ 11,697 (2) Included in payable to brokers, dealers and clearing organizations on the consolidated balance sheet. As of December 31, 2024 (Expressed in thousands) Gross Amounts Not Offset on the Balance Sheet Gross Amounts of Recognized Assets Gross Amounts Offset on the Balance Sheet Net Amounts of Assets Presented on the Balance Sheet Financial Instruments Cash Collateral Received Net Amount Reverse repurchase agreements $ 68,055 $ ( 68,055 ) $ — $ — $ — $ — Securities borrowed (1) 137,177 — 137,177 ( 130,568 ) — 6,609 Total $ 205,232 $ ( 68,055 ) $ 137,177 $ ( 130,568 ) $ — $ 6,609 (1) Included in receivable from brokers, dealers and clearing organizations on the condensed consolidated balance sheet. (Expressed in thousands) Gross Amounts Not Offset on the Balance Sheet Gross Amounts of Recognized Liabilities Gross Amounts Offset on the Balance Sheet Net Amounts of Liabilities Presented on the Balance Sheet Financial Instruments Cash Collateral Pledged Net Amount Repurchase agreements $ 999,809 $ ( 68,055 ) $ 931,754 $ ( 931,754 ) $ — $ — Securities loaned (2) 235,498 — 235,498 ( 229,156 ) — 6,342 Total $ 1,235,307 $ ( 68,055 ) $ 1,167,252 $ ( 1,160,910 ) $ — $ 6,342 (2) Included in payable to brokers, dealers and clearing organizations on the consolidated balance sheet. 28 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) The Company receives collateral in connection with securities borrowed and reverse repurchase agreement transactions and customer margin loans. Under many agreements, the Company is permitted to sell or re-pledge the securities received (e.g., use the securities to enter into securities lending transactions, or deliver to counterparties to cover short positions). As of June 30, 2025, the fair value of securities received as collateral under securities borrowed transactions and reverse repurchase agreements was $ 137.1 million ($ 131.7 million as of December 31, 2024) and $ 192.8 million ($ 68.1 million as of December 31, 2024), respectively, of which the Company has sold and re-pledged approximately $ 51.5 million ($ 39.2 million as of December 31, 2024) under securities loaned transactions and $ 192.8 million under repurchase agreements ($ 68.1 million as of December 31, 2024). 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 $ 1.1 billion, as presented on the face of the consolidated balance sheet as of June 30, 2025 ($ 1.0 billion as of December 31, 2024). 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. The Company manages market risk of repurchase agreements and securities loaned by monitoring the market value of collateral held and the market value of securities receivable from others. It is the Company's policy to request and obtain additional collateral when exposure to loss exists. In the event the counterparty is unable to meet its contractual obligation to return the securities, the Company may be exposed to off-balance sheet risk of acquiring securities at prevailing market prices. Credit Concentrations Credit concentrations may arise from trading, investing, underwriting and financing activities and may be impacted by changes in economic, industry or political factors. In the normal course of business, the Company may be exposed to credit risk in the event customers, counterparties including other brokers and dealers, issuers, banks, depositories or clearing organizations are unable to fulfill their contractual obligations. 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 June 30, 2025 were receivables from three major U.S. broker-dealers totaling approximately $ 99.4 million. Included in receivable from customers as of June 30, 2025 were fully secured margin loans from our two largest customer accounts totaling approximately $ 653.2 million, comprising 49.5 % of total margin loans. The Company is obligated to settle transactions with brokers and other financial institutions even if its clients fail to meet their obligations to the Company. Clients are required to complete their transactions on the settlement date, generally one business day after the trade date. 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"), the Mortgage-Backed Securities Division (a division of the FICC), the Options Clearing Corporation and others. With respect to its business in reverse repurchase and repurchase agreements, all open contracts as of June 30, 2025 are with the FICC . In addition, the Company clears its non-U.S. international equities business carried on by Oppenheimer Europe Ltd. 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. 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. As of June 30, 2025, the Company had recorded no liabilities with regard to this right. The Company's policy is to monitor the credit standing of the clearing brokers and banks with which it conducts business. 29 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 10. Variable interest entities ("VIEs") The Company's policy is to consolidate all subsidiaries in which it has a controlling financial interest, as well as any VIEs where the Company is deemed to be the primary beneficiary, when it has the power to make the decisions that most significantly affect the economic performance of the VIE and has the obligation to absorb significant losses or the right to receive benefits that could potentially be significant to the VIE. The Company serves as general partner of hedge funds and private equity funds that were established for the purpose of providing alternative investments to both its institutional and qualified retail clients. The Company's investment in and additional capital commitments to these hedge funds and private equity funds are considered variable interests. The Company's additional capital commitments are subject to call at a later date and are limited to the amount committed. The Company assesses whether it is the primary beneficiary of the hedge funds and private equity funds in which it holds a variable interest in the form of general and limited partner interests. In each instance, the Company has determined that it is not the primary beneficiary and therefore need not consolidate the hedge funds or private equity funds. The subsidiaries' general and limited partnership interests and additional capital commitments represent its maximum exposure to loss. The subsidiaries' general partnership and limited partnership interests are included in other assets on the condensed consolidated balance sheet. As of June 30, 2025 and December 31, 2024, assets and liabilities related to a VIE where the Company is not the primary beneficiary were included in Securities owned, at fair value on the consolidated balance sheet and primarily related to a convertible note and warrants issued by a beverage manufacturing company. The maximum loss exposure indicated in the following table relates solely to our investments in, and unfunded commitments to, the VIE. (Expressed in thousands) As of June 30, 2025 2024 Assets $ 3,052 $ — Liabilities — — Unfunded commitments — — Maximum loss exposure $ 3,052 $ — 11. Income taxes The effective income tax rate for the three and six months ended June 30, 2025 was 32.7 % and 28.9 %, respectively, compared with 35.3 % and 32.5 % for the three and six month ended June 30, 2024, respectively, and reflects the Company's annual estimate of the statutory federal and state tax rates adjusted for certain discrete items. The effective tax rate for the second quarter of 2025 was positively impacted by higher net income which diluted the unfavorable impact of certain permanent items and nondeductible foreign losses. 30 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 12. Stockholders' Equity The Company's authorized shares consist of (a) 50,000,000 shares of Preferred Stock, par value $ 0.001 per share; (b) 50,000,000 shares of Class A Stock, par value $ 0.001 per share; and (c) 99,665 shares of Class B Stock, par value $ 0.001 per share. No Preferred Stock has been issued. 99,665 shares of Class B Stock have been issued and are outstanding. The Class A Stock and the Class B Stock are equal in all respects except that the Class A Stock is non-voting. The following table reflects changes in the number of shares of Class A Stock outstanding for the periods indicated: For the Three Months Ended June 30, For the Six Months Ended June 30, 2025 2024 2025 2024 Class A Stock outstanding, beginning of period 10,425,830 10,247,197 10,231,736 10,186,783 Issued pursuant to share-based compensation plans 2,284 3,750 197,908 278,887 Repurchased and cancelled ( 9,855 ) ( 23,102 ) ( 11,385 ) ( 237,825 ) Class A Stock outstanding, end of period 10,418,259 10,227,845 10,418,259 10,227,845 Stock buy-back On March 1, 2024, the Company's 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 5.0 % of its 10,357,376 then issued and outstanding shares of Class A Stock. During the year ended December 31, 2024, the Company purchased and canceled an aggregate of 243,806 shares of Class A Stock for a total consideration of $ 9.6 million ($ 39.39 per share) under its share repurchase program. As of December 31, 2024, 497,893 shares remained available to be purchased under its share repurchase program. During the three months ended June 30, 2025, the Company purchased and canceled an aggregate of 9,855 shares of Class A Stock for a total consideration of $ 580,396 ($ 58.89 per share) under its share repurchase program. During the six months ended June 30, 2025, the Company purchased and canceled an aggregate of 11,385 shares of Class A Stock for a total consideration of $ 670,346 ($ 58.88 per share) under its share repurchase program. During the three months ended June 30, 2024, the Company purchased and canceled an aggregate of 23,102 shares of Class A Stock for a total consideration of $ 924,364 ($ 40.01 per share) under this program. During the six months ended June 30, 2024, the Company purchased and canceled an aggregate of 237,825 shares of Class A Stock for a total consideration of $ 9.3 million ($ 39.14 per share) under this program. As of June 30, 2025, 486,508 shares remained available to be purchased under the share repurchase program. 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. All shares purchased will be canceled. The share repurchase program is expected to continue indefinitely. The timing and amounts of any purchases will be based on market conditions and other factors including price, regulatory requirements and capital availability. The share repurchase program does not obligate the Company to repurchase any dollar amount or number of shares of Class A Stock. Depending on market conditions and other factors, these repurchases may be commenced or suspended from time to time without prior notice. On August 1, 2025, the Company announced a quarterly dividend in the amount of $ 0.18 per share, payable on August 29, 2025 to holders of Class A Stock and Class B Stock of record on August 15, 2025. 31 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 13. Contingencies Many aspects of the Company's business involve substantial risks of liability. In the normal course of business, the Company has been named as defendant or co-defendant in various legal actions, including arbitrations, class actions and other litigation, creating substantial exposure and periodic expenses. Certain of the actual or threatened legal matters include claims for substantial compensatory and/or punitive damages or claims for indeterminate amounts of damages. These proceedings arise primarily from securities brokerage, asset management and investment banking activities. 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 Securities and Exchange Commmission (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 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 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. For legal and regulatory proceedings where there is at least a reasonable possibility that a loss or an additional loss may be incurred, the Company estimates a range of aggregate loss in excess of amounts accrued of up to $ 3 million. This estimated aggregate range is based upon currently available information for those legal proceedings in which the Company is involved, where the Company can make an estimate for such losses. For certain cases, the Company does not believe that it can make an estimate. The foregoing aggregate estimate is based on various factors, including the varying stages of the proceedings (including the fact that some are currently in preliminary stages), the numerous yet-unresolved issues in many of the proceedings and the attendant uncertainty of the various potential outcomes of such proceedings. 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 was named as a respondent in numerous 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 from any of the investors prior to the SEC bringing a complaint against Woods and his co-conspirators in 2021. Oppenheimer has settled or an award has been rendered and paid in all but one of the Horizon-related arbitrations. In addition, in June and August of 2023, Oppenheimer was served with two Horizon-related complaints in Georgia State Court, by plaintiffs, virtually all of whom were never Oppenheimer customers, alleging unspecified losses. In 2024, each of those complaints was dismissed by the trial court. Plaintiffs in each case subsequently filed an appeal of the court’s order dismissing 32 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) the cases. In May of 2025, the Georgia Court of Appeals upheld the trial court’s decision dismissing the cases. In May of 2025, plaintiffs filed a writ of certiorari with the Georgia Supreme Court which is currently pending. On June 30, 2022, 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 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. 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 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. In June 2025, Oppenheimer was served with a complaint in an action entitled Liberty Capital Group v. Oppenheimer Holdings Inc., Oppenheimer & Co. Inc. and Oppenheimer Asset Management Inc., filed in the United States District Court for the Southern District of New York. Plaintiffs seek class certification and allege that defendants used Oppenheimer’s Advantage Bank Deposit Sweep Program to unlawfully enrich themselves, and accordingly, breached their fiduciary duties and contractual obligations to their customers and otherwise violated New York law. Plaintiffs allege unspecified damages to be proven at trial. Defendants intend to vigorously defend themselves against the allegations in the complaint. 14. Regulatory requirements The Company's U.S. broker dealer subsidiaries, Oppenheimer and Freedom, are subject to the uniform net capital requirements of the SEC under Rule 15c3-1 (the "Rule") promulgated under the Exchange Act. Oppenheimer computes its net capital requirements under the alternative method provided for in the Rule which requires that Oppenheimer maintain net capital equal to two percent of aggregate customer-related debit items, as defined in SEC Rule 15c3-3. As of June 30, 2025, the net capital of Oppenheimer as calculated under the Rule was $ 408.9 million or 30.56 % of Oppenheimer's aggregate debit items. This was $ 382.2 million in excess of the minimum required net capital at that date. Freedom computes its net capital requirement under the basic method provided for in the Rule, which requires that Freedom maintain net capital equal to the greater of $ 100,000 or 6-2/3% of aggregate indebtedness, as defined. As of June 30, 2025, Freedom had net capital of $ 3.6 million, which was $ 3.5 million in excess of the $ 100,000 required to be maintained at that date. As of June 30, 2025, the capital required and held under the Financial Conduct Authority's Investment Firms’ Prudential Regime (“IFPR”) for Oppenheimer Europe Ltd. was as follows: • Common Equity Tier 1 ratio 107 % (required 56.0 %); • Tier 1 Capital ratio 107 % (required 75.0 %); and • Total Capital ratio 144 % (required 100.0 %). As of June 30, 2025, Oppenheimer Europe Ltd. was in compliance with its regulatory requirements. As of June 30, 2025, the regulatory capital of Oppenheimer Investments Asia Limited was $ 2.1 million, which was $ 1.7 million in excess of the $ 382,168 required to be maintained on that date. Oppenheimer Investments Asia Limited computes its regulatory capital pursuant to the requirements of the Securities and Futures Commission of Hong Kong. As of June 30, 2025, Oppenheimer Investments Asia Limited was in compliance with its regulatory requirements. As of June 30, 2025, Oppenheimer Trust is required to maintain minimal capital of $ 4.15 million. Oppenheimer Trust is currently in compliance with its capital requirements. 33 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 15. Segment information The Company has determined its reportable segments based on the Company's method of internal reporting, which disaggregates its retail business by branch and its proprietary and investment banking businesses by product. The Company’s chief operating decision maker (“CODM”) is the chief executive officer. The CODM evaluates the performance of the Company’s reportable segments based on their year-over-year revenue and pre-tax profit or loss and uses these measures to allocate resources (including employee, financial and/or capital resources), largely in conjunction with monthly and/or quarterly reviews of segment financial performance. The CODM also uses segment profit or loss in evaluating the incentive and other compensation of segment employees as well as capital investment for facilities and information technology development. Effective in the fourth quarter of 2024, the Company combined the former Private Client and Asset Management business segments to form the Wealth Management segment. The revised segment structure is aligned with how the CODM and senior management view the performance and operations of our retail focused business. Our Capital Markets and Corporate/Other segments were not impacted by these changes. To provide historical information on a basis consistent with the revised segment presentation, the Company recast prior period segment results. The Company's reportable segments are: Wealth Management — includes commissions and fee income earned on assets under management ("AUM"), net interest earnings on client margin loans and cash balances, fees from money market funds, custodian fees, net contributions from stock loan activities and financing activities, and direct expenses; and Capital Markets — includes investment banking, institutional equities sales, trading, and research, taxable fixed income sales, trading, and research, public finance and municipal trading, as well as the Company's operations in the United Kingdom, Hong Kong and Israel, and direct expenses associated with this segment. The Company does not allocate costs associated with certain infrastructure support groups that are centrally managed for its reportable segments. These areas include, but are not limited to, legal, compliance, operations, accounting, and internal audit. Costs associated with these groups are separately reported in a Corporate/Other category and primarily include compensation and benefits. The costs of certain centralized or shared functions are allocated based on methodologies that reflect utilization. The Company also includes activities associated with BondWave, LLC, an indirectly wholly owned subsidiary, in Corporate/Other. The tables below present information about the Company’s reported segment revenues, segment pre-tax income or loss, compensation expenses, and other segment items for the three and six months ended June 30, 2025 and 2024. There are no adjustments or reconciling items for any of the periods presented. Asset information by reportable segment is not reported, since the Company does not produce such information for internal use by the CODM. (Expressed in thousands) For the Three Months Ended June 30, 2025 Wealth Management Capital Markets Corporate/Other Total Revenue $ 246,421 $ 122,981 $ 3,776 $ 373,178 Less : Compensation Expenses 132,291 80,610 26,173 239,074 Other Segment Items (1) 51,296 46,235 4,363 101,894 Pre-Tax Income (Loss) $ 62,834 $ ( 3,864 ) $ ( 26,760 ) $ 32,210 (1) Other segment items include communication and technology expenses, occupancy and equipment costs, clearing and exchange fees, interest and other expenses. 34 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) (Expressed in thousands) For the Three Months Ended June 30, 2024 Wealth Management Capital Markets Corporate/Other Total Revenue $ 234,526 $ 92,141 $ 3,922 $ 330,589 Less : Compensation Expenses 123,538 73,290 23,899 220,727 Other Segment Items (1) 46,757 40,626 6,614 93,997 Pre-Tax Income (Loss) $ 64,231 $ ( 21,775 ) $ ( 26,591 ) $ 15,865 (1) Other segment items include communication and technology expenses, occupancy and equipment costs, clearing and exchange fees, interest and other expenses. (Expressed in thousands) For the Six Months Ended June 30, 2025 Wealth Management Capital Markets Corporate/Other Total Revenue $ 488,407 $ 246,242 $ 6,354 $ 741,003 Less : Compensation Expenses 251,939 167,954 46,272 466,165 Other Segment Items (1) 105,770 87,249 8,233 201,252 Pre-Tax Income (Loss) $ 130,698 $ ( 8,961 ) $ ( 48,151 ) $ 73,586 (1) Other segment items include communication and technology expenses, occupancy and equipment costs, clearing and exchange fees, interest and other expenses. (Expressed in thousands) For the Six Months Ended June 30, 2024 Wealth Management Capital Markets Corporate/Other Total Revenue $ 472,487 $ 204,224 $ 7,016 $ 683,727 Less : Compensation Expenses 239,111 154,878 48,453 442,442 Other Segment Items (1) 93,360 77,823 16,782 187,965 Pre-Tax Income (Loss) $ 140,016 $ ( 28,477 ) $ ( 58,219 ) $ 53,320 (1) Other segment items include communication and technology expenses, occupancy and equipment costs, clearing and exchange fees, interest and other expenses. Revenue, classified by the major geographic areas in which it was earned, for the three months ended June 30, 2025 and 2024 was: (Expressed in thousands) For the Three Months Ended June 30, For the Six Months Ended June 30, 2025 2024 2025 2024 Americas $ 358,813 $ 316,467 $ 713,521 $ 657,884 Europe/Middle East 13,737 13,394 26,090 24,168 Asia 628 728 1,392 1,675 Total $ 373,178 $ 330,589 $ 741,003 $ 683,727 35 Table of Contents OPPENHEIMER HOLDINGS INC. Notes to Condensed Consolidated Financial Statements (unaudited) 16. Subsequent events The Company has performed an evaluation of events that occurred since June 30, 2025 and through the date on which the condensed consolidated financial statements were issued, and determined t here are no events that have occurred that would require recognition or additional disclosure except as disclosed in Note 12 related to the Company's declaration of a quarterly dividend. 36 Table of Contents