OPY / Oppenheimer Holdings Inc. - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

Oppenheimer Holdings Inc.
US ˙ NYSE ˙ US6837971042

Mga Batayang Estadistika
CIK 791963
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Oppenheimer Holdings Inc.
SEC Filings (Chronological Order)
Halaman ini menyediakan daftar lengkap dan kronologis dari Pengajuan SEC, tidak termasuk pengajuan kepemilikan yang kami sediakan di tempat lain.
August 4, 2025 EX-99.1

Oppenheimer Holdings Inc. Second Quarter 2025 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may con

opy2q2025investorpresent Oppenheimer Holdings Inc. Second Quarter 2025 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21

August 4, 2025 8-K

As filed with the Securities and Exchange Commission on August 4, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of repo

As filed with the Securities and Exchange Commission on August 4, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

August 1, 2025 EX-99.1

Oppenheimer Holdings Inc. Reports Second Quarter 2025 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Second Quarter 2025 Earnings New York, August 1, 2025 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $21.7 million or $2.06 basic earnings per share for the second quarter of 2025, compared with net income of $10.3 million or $0.99 basic earnings per share for the second quarter of 2024. Revenue for the

August 1, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1-

August 1, 2025 8-K

As filed with the Securities and Exchange Commission on August 1, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of repo

As filed with the Securities and Exchange Commission on August 1, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

June 4, 2025 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K (Mark One): ☒ ANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the fiscal year ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the transition period from to Commission File Number 8-04077 A. Full title of the plan

May 6, 2025 8-K

As filed with the Securities and Exchange Commission on May 6, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of report

As filed with the Securities and Exchange Commission on May 6, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

May 6, 2025 EX-99.1

Oppenheimer Holdings Inc. New York, NY May 5, 2025 Annual Stockholders' Meeting WELCOME to Oppenheimer's 2025 Annual Stockholders' Meeting May 5, 2025 2 Safe Harbor Statement This presentation and other written or oral statements made from time to ti

Oppenheimer Holdings Inc. New York, NY May 5, 2025 Annual Stockholders' Meeting WELCOME to Oppenheimer's 2025 Annual Stockholders' Meeting May 5, 2025 2 Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Sec

April 28, 2025 EX-99.1

Oppenheimer Holdings Inc. First Quarter 2025 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may cont

Oppenheimer Holdings Inc. First Quarter 2025 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchan

April 28, 2025 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on April 28, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

April 25, 2025 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on April 25, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

April 25, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1

April 25, 2025 EX-99.1

Oppenheimer Holdings Inc. Reports First Quarter 2025 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports First Quarter 2025 Earnings New York, April 25, 2025 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $30.7 million or $2.93 basic earnings per share for the first quarter of 2025, compared with net income of $26.1 million or $2.50 basic earnings per share for the first quarter of 2024. Revenue for the fir

March 14, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the registrant ☒ Filed by a party other than the registrant ☐ Check the appropriate box: ☐ Preliminary proxy statement ☐ Confidential, for use of

March 5, 2025 ARS

OPPENHEIMER HOLDINGS INC. Annual Report 2024 2024 2023 2022 2021 2020 In thousands except per share amounts and number of employees Gross revenue $1,432,496 $1,248,825 $1,110,941 $1,394,035 $1,198,667 Income before income taxes $105,757 $46,770 $45,5

OPPENHEIMER HOLDINGS INC. Annual Report 2024 2024 2023 2022 2021 2020 In thousands except per share amounts and number of employees Gross revenue $1,432,496 $1,248,825 $1,110,941 $1,394,035 $1,198,667 Income before income taxes $105,757 $46,770 $45,554 $224,641 $169,000 Net income* $71,557 $30,179 $32,351 $158,964 $122,986 Basic earnings per share* $6.91 $2.81 $2.77 $12.57 $9.73 Total assets $3,38

February 27, 2025 EX-21

Subsidiaries of the registrant (filed herewith).

EXHIBIT 21 Subsidiaries of Oppenheimer Holdings Inc. As of December 31, 2024 Pursuant to Item 601(b)(21)(ii) of Regulation S-K, the names of certain other subsidiaries of Oppenheimer are omitted because, considered in the aggregate as a single subsidiary, they would not constitute a "significant subsidiary" as that term is defined in Rule 1-02(w) of Regulation S-X under the Securities Exchange Act

February 27, 2025 10-K

For the fiscal year ended December 31, 2024

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 OMB APPROVAL OMB Number: 3235-0063 Expires: May 31, 2025 Estimated average burden hours per response . . . 2,255.26 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR o TRANSITION REPORT PURSUANT TO SECTION

February 27, 2025 EX-99.1

OPPENHEIMER HOLDINGS INC. ANNOUNCES CEO SUCCESSION ALBERT G. LOWENTHAL TRANSITIONS TO EXECUTIVE CHAIRMAN ROBERT S. LOWENTHAL APPOINTED CEO & PRESIDENT

OPPENHEIMER HOLDINGS INC. ANNOUNCES CEO SUCCESSION ALBERT G. LOWENTHAL TRANSITIONS TO EXECUTIVE CHAIRMAN ROBERT S. LOWENTHAL APPOINTED CEO & PRESIDENT NEW YORK, February 27, 2025 – Oppenheimer Holdings Inc. today announced that Albert G. Lowenthal, Chairman of the Board of Directors and Chief Executive Officer (CEO), would step down as CEO of the Company and its primary operating subsidiary, Oppen

February 27, 2025 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

As filed with the Securities and Exchange Commission on February 27, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

February 27, 2025 EX-22

Subsidiary Guarantors and Issuers of Registered Senior Secured Notes (filed herewith).

Exhibit 22 Subsidiary Guarantors and Issuers of Registered Senior Secured Notes Oppenheimer Holdings, Inc.

February 27, 2025 EX-19

Insider Trading Policy (filed herewith).

1 Insider Trading Policy Updated January 2025 Purpose This Insider Trading Policy (this “Policy”) provides guidelines with respect to transactions in the securities of Oppenheimer Holdings Inc.

February 3, 2025 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on February 3, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

February 3, 2025 EX-99.1

Oppenheimer Holdings Inc. Fourth Quarter and Full Year 2024 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “com

Oppenheimer Holdings Inc. Fourth Quarter and Full Year 2024 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Se

January 31, 2025 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on January 31, 2025 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

January 31, 2025 EX-99.1

Oppenheimer Holdings Inc. Reports Fourth Quarter and Full Year 2024 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Fourth Quarter and Full Year 2024 Earnings New York, January 31, 2025 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $10.7 million or $1.04 basic earnings per share for the fourth quarter of 2024 compared with net income of $11.1 million or $1.07 basic earnings per share for the fourth quarter of 2023. F

October 28, 2024 EX-99.1

Oppenheimer Holdings Inc. Third Quarter 2024 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may cont

Oppenheimer Holdings Inc. Third Quarter 2024 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchan

October 28, 2024 8-K

As filed with the Securities and Exchange Commission on October 28, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of re

As filed with the Securities and Exchange Commission on October 28, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

October 25, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Numb

October 25, 2024 EX-99.1

Oppenheimer Holdings Inc. Reports Third Quarter 2024 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Third Quarter 2024 Earnings New York, October 25, 2024 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $24.5 million or $2.38 basic earnings per share for the third quarter of 2024, compared with net income of $13.9 million or $1.32 basic earnings per share for the third quarter of 2023. Revenue for the t

October 25, 2024 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on October 25, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

September 19, 2024 8-K

Termination of a Material Definitive Agreement, Financial Statements and Exhibits

As filed with the Securities and Exchange Commission on September 19, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 29, 2024 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on July 29, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 29, 2024 EX-99.1

Oppenheimer Holdings Inc. Second Quarter 2024 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may con

Oppenheimer Holdings Inc. Second Quarter 2024 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Excha

July 26, 2024 EX-10.1

10.1 to Quarterly Report on Form 10-Q for the quarter ended June 30, 2024 filed with the SEC on July 26, 2024

143400740v10 OPPENHEIMER HOLDINGS INC. 2024 INCENTIVE PLAN (Effective May 6, 2024) 143400740v10 OPPENHEIMER HOLDINGS INC. 2024 INCENTIVE PLAN (Effective May 6, 2024) ARTICLE I PURPOSE The purpose of the Oppenheimer Holdings Inc. 2024 Incentive Plan (the “Plan”), effective May 6, 2024, the date that the Plan is approved by the Company’s Class B stockholders (the “Effective Date”) is to enhance the

July 26, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1-

July 26, 2024 EX-99.1

Oppenheimer Holdings Inc. Reports Second Quarter 2024 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Second Quarter 2024 Earnings New York, July 26, 2024 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $10.3 million or $0.99 basic earnings per share for the second quarter of 2024, compared with a net loss of $(9.4) million or $(0.85) basic earnings per share for the second quarter of 2023. Revenue for th

July 26, 2024 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on July 26, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

June 10, 2024 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K (Mark One): ☒ ANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the fiscal year ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the transition period from to Commission File Number 8-04077 A. Full title of the plan

May 8, 2024 S-8

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933, AS AMENDED OPPENHEIMER HOLDINGS INC. (Exact name of Registrant as Specified in its Charter) Delaware 98-0080034

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933, AS AMENDED OPPENHEIMER HOLDINGS INC. (Exact name of Registrant as Specified in its Charter) Delaware 98-0080034 (State or Other Jurisdiction of (I.R.S. Employer Incorporation or Organization) Identification No.) 85 Broad Street New York, NY 10004 (Address, incl

May 8, 2024 EX-FILING FEES

Filing Fee Table (filed herewith).

EXHIBIT 107 FILING FEE TABLE Calculation of Filing Fee Tables Form S-8 (Form Type) Oppenheimer Holdings Inc.

May 7, 2024 EX-99.1

Annual Stockholders’ Meeting New York, NY May 6, 2024 Oppenheimer Holdings Inc. WELCOME to Oppenheimer’s 2024 Annual Stockholders’ Meeting May 6, 2024 2 Safe Harbor Statement This presentation and other written or oral statements made from time to ti

Annual Stockholders’ Meeting New York, NY May 6, 2024 Oppenheimer Holdings Inc. WELCOME to Oppenheimer’s 2024 Annual Stockholders’ Meeting May 6, 2024 2 Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward‐looking statements” within the meaning of Sec

May 7, 2024 8-K

Current Report

As filed with the Securities and Exchange Commission on May 7, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

May 7, 2024 EX-10.1

Oppenheimer Holdings Inc. 2024 Incentive Plan (Effective May 6, 2024)

143400740v10 OPPENHEIMER HOLDINGS INC. 2024 INCENTIVE PLAN (Effective May 6, 2024) 143400740v10 OPPENHEIMER HOLDINGS INC. 2024 INCENTIVE PLAN (Effective May 6, 2024) ARTICLE I PURPOSE The purpose of the Oppenheimer Holdings Inc. 2024 Incentive Plan (the “Plan”), effective May [], 2024, the date that the Plan is approved by the Company’s Class B stockholders (the “Effective Date”) is to enhance the

April 29, 2024 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on April 29, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

April 29, 2024 EX-99.1

Oppenheimer Holdings Inc. First Quarter 2024 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may cont

Oppenheimer Holdings Inc. First Quarter 2024 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchan

April 26, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1

April 26, 2024 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on April 26, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

April 26, 2024 EX-99.1

Oppenheimer Holdings Inc. Reports First Quarter 2024 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports First Quarter 2024 Earnings New York, April 26, 2024 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $26.1 million or $2.50 basic earnings per share for the first quarter of 2024, an increase of approximately 78.2%, compared with net income of $14.6 million or $1.32 basic earnings per share for the first

March 15, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the registrant ☒ Filed by a party other than the registrant ☐ Check the appropriate box: ☐ Preliminary proxy statement ☐ Confidential, for use of

March 4, 2024 8-K

Financial Statements and Exhibits, Other Events

As filed with the Securities and Exchange Commission on March 4, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

March 1, 2024 EX-21.1

Subsidiaries of the registrant (filed herewith).

EXHIBIT 21 Subsidiaries of Oppenheimer Holdings Inc. As of December 31, 2023 Pursuant to Item 601(b)(21)(ii) of Regulation S-K, the names of certain other subsidiaries of Oppenheimer are omitted because, considered in the aggregate as a single subsidiary, they would not constitute a "significant subsidiary" as that term is defined in Rule 1-02(w) of Regulation S-X under the Securities Exchange Act

March 1, 2024 EX-97

Oppenheimer Holdings Inc. Compensation Recovery (Clawback) Policy adopted January 2011 and amended October 2023 (

OPPENHEIMER HOLDINGS INC. COMPENSATION RECOVERY (CLAWBACK) POLICY Introduction The Board of Directors (the "Board") of Oppenheimer Holdings Inc. (the “Company”) believes that it is in the best interests of the Company and its shareholders to create and maintain a culture that emphasizes integrity and accountability and that reinforces the Company's pay-for- performance compensation philosophy. The

March 1, 2024 10-K

For the fiscal year ended December 31, 2023

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 OMB APPROVAL OMB Number: 3235-0063 Expires: May 31, 2025 Estimated average burden hours per response . . . 2,255.26 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR o TRANSITION REPORT PURSUANT TO SECTION

March 1, 2024 ARS

OPPENHEIMER HOLDINGS INC. Annual Report 2023 $4.10 $9.73 $12.57 $2.77 $2.81 19 20 21 22 23 2023 2022 2021 2020 2019 In thousands except per share amounts and number of employees Gross revenue $1,248,825 $1,110,941 $1,394,035 $1,198,667 $1,033,379 Inc

OPPENHEIMER HOLDINGS INC. Annual Report 2023 $4.10 $9.73 $12.57 $2.77 $2.81 19 20 21 22 23 2023 2022 2021 2020 2019 In thousands except per share amounts and number of employees Gross revenue $1,248,825 $1,110,941 $1,394,035 $1,198,667 $1,033,379 Income before income taxes $46,770 $45,554 $224,641 $169,000 $74,912 Net income $30,179 $32,351 $158,964 $122,986 $52,953 Basic earnings per share $2.81

March 1, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

As filed with the Securities and Exchange Commission on March 1, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

March 1, 2024 EX-4.3

Description of the Registrant's Common Stock (filed herewith).

Exhibit 4.3 153872149.1 DESCRIPTION OF THE REGISTRANT’S COMMON STOCK Oppenheimer Holdings Inc. is incorporated in the State of Delaware. The rights of our stockholders and the terms of our common stock are generally covered by Delaware law, including the Delaware General Corporation Law, and our certificate of incorporation and amended and restated by-laws which are filed as exhibits to our Annual

March 1, 2024 EX-22.1

Subsidiary Guarantors and Issuers of Registered Senior Secured Notes (filed herewith).

Exhibit 22 Subsidiary Guarantors and Issuers of Registered Senior Secured Notes Oppenheimer Holdings, Inc.

January 29, 2024 EX-99.1

Oppenheimer Holdings Inc. Fourth Quarter and Full Year 2023 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “com

Oppenheimer Holdings Inc. Fourth Quarter and Full Year 2023 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Se

January 29, 2024 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on January 29, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

January 26, 2024 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on January 26, 2024 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

January 26, 2024 EX-99.1

Oppenheimer Holdings Inc. Reports Fourth Quarter and Full Year 2023 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Fourth Quarter and Full Year 2023 Earnings New York, January 26, 2024 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $11.1 million or $1.07 basic earnings per share for the fourth quarter of 2023 compared with net income of $22.4 million or $2.04 basic earnings per share for the fourth quarter of 2022. A

January 24, 2024 EX-FILING FEES

Filing Fee Table (filed herewith).

EXHIBIT 107 FILING FEE TABLE Calculation of Filing Fee Tables Form S-8 (Form Type) Oppenheimer Holdings Inc.

January 24, 2024 S-8

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933, AS AMENDED OPPENHEIMER HOLDINGS INC. (Exact name of Registrant as Specified in its Charter) Delaware 98-0080034

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933, AS AMENDED OPPENHEIMER HOLDINGS INC. (Exact name of Registrant as Specified in its Charter) Delaware 98-0080034 (State or Other Jurisdiction of (I.R.S. Employer Incorporation or Organization) Identification No.) 85 Broad Street New York, NY 10004 (Address, incl

January 24, 2024 EX-24.1

Power of Attorney (included on the signature pages of this registration statement).

EXHIBIT 24.1 POWER OF ATTORNEY Each person whose signature appears below hereby constitutes and appoints Brad M. Watkins, his or her true and lawful attorney-in-fact and agent, with full power of substitution and resubstitution, for him or her and in his or her name, place and stead, in any and all capacities, to sign any or all amendments or supplements (including post-effective amendments) to th

October 30, 2023 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on October 30, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

October 30, 2023 EX-99.1

Oppenheimer Holdings Inc. Third Quarter 2023 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may cont

Oppenheimer Holdings Inc. Third Quarter 2023 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchan

October 27, 2023 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on October 27, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

October 27, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Numb

October 27, 2023 EX-99.1

Oppenheimer Holdings Inc. Reports Third Quarter 2023 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Third Quarter 2023 Earnings New York, October 27, 2023 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $13.9 million or $1.32 basic earnings per share for the third quarter of 2023, an increase of approximately 206.7%, compared with net income of $4.5 million or $0.40 basic earnings per share for the thir

October 25, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

As filed with the Securities and Exchange Commission on October 25, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 31, 2023 8-K

As filed with the Securities and Exchange Commission on July 31, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of repor

As filed with the Securities and Exchange Commission on July 31, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 31, 2023 EX-99.1

Oppenheimer Holdings Inc. Second Quarter 2023 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may con

opyq2-2023investorpresen Oppenheimer Holdings Inc. Second Quarter 2023 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21

July 28, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1-

July 28, 2023 8-K

As filed with the Securities and Exchange Commission on July 28, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of repor

As filed with the Securities and Exchange Commission on July 28, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 28, 2023 EX-99.1

Oppenheimer Holdings Inc. Reports Second Quarter 2023 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Second Quarter 2023 Earnings New York, July 28, 2023 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported a net loss of $9.4 million or $(0.85) per share for the second quarter of 2023, compared with a net loss of $3.9 million or $(0.32) per share for the second quarter of 2022. Revenue for the second quarter of 2023 was $3

July 28, 2023 EX-10.12

Third Amendment to Agreement of Lease dated June 13, 2023 between 666 Third Avenue LLC (Landlord) and Viner Finance Inc., Tenant for premises at 45 Rockefeller Plaza, New York, NY.

THIRD AMENDMENT TO LEASE This THIRD AMENDMENT TO LEASE (this “Amendment”) made as of thisday of June, 2023, by and between 666 THIRD AVENUE, L.

July 6, 2023 EX-99.(A)(5)(C)

Press release announcing final results of the Tender Offer, dated July 6, 2023.

Exhibit (a)(5)(C) Oppenheimer Holdings Inc. Announces Final Results of Modified Dutch Auction Tender Offer New York — July 6, 2023 – Oppenheimer Holdings Inc. (the “Company”) (NYSE: OPY) today announced final results of its modified “Dutch auction” tender offer which expired 11:59 p.m., New York City time, on Wednesday, June 28, 2023. Based on the final count by Computershare Trust Company, N.A.,

July 6, 2023 SC TO-I/A

United states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 2) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) or 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 OPPENHEIMER HOLDINGS INC. (Name of Subject Company

United states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 2) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) or 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 OPPENHEIMER HOLDINGS INC. (Name of Subject Company (Issuer) and Filing Person (Offeror)) Class A non-voting common stock, par value $0.001 per share (Title of Class of Securities) 671005106 (CUSIP Numb

June 29, 2023 SC TO-I/A

United states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 1) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) or 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 OPPENHEIMER HOLDINGS INC. (Name of Subject Company

United states SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO (Amendment No. 1) TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) or 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 OPPENHEIMER HOLDINGS INC. (Name of Subject Company (Issuer) and Filing Person (Offeror)) Class A non-voting common stock, par value $0.001 per share (Title of Class of Securities) 671005106 (CUSIP Numb

June 29, 2023 EX-99.(A)(5)(B)

Press release announcing preliminary results of the Tender Offer, dated June 29, 2023.

Exhibit (a)(5)(B) Oppenheimer Holdings Inc. Announces Preliminary Results of Modified Dutch Auction Tender Offer New York — June 29, 2023 — Oppenheimer Holdings Inc. (the “Company”) (NYSE: OPY) today announced preliminary results of its modified “Dutch auction” tender offer which expired at 11:59 p.m., New York City time, on Wednesday, June 28, 2023. Based on the preliminary count by Computershare

June 8, 2023 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K (Mark One): ☒ ANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the fiscal year ended December 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the transition period from to Commission File Number 8-04077 A. Full title of the plan

May 31, 2023 EX-99.(A)(1)(C)

Notice of Guaranteed Delivery.

 Exhibit (a)(1)(C) NOTICE OF GUARANTEED DELIVERY (Not to be used for Signature Guarantee) for Tender of Shares of Class A non-voting common stock of Oppenheimer Holdings Inc.

May 31, 2023 EX-99.(A)(1)(E)

Letter to Clients for Use by Brokers, Dealers, Commercial Banks, Trust Companies and Other Nominees, dated May 31, 2023.

 Exhibit (a)(1)(E) Offer to Purchase by Oppenheimer Holdings Inc. for an Aggregate Purchase Price of Up to $30,000,000 in Cash of Shares of its Class A non-voting common stock at a Purchase Price Not Greater than $40.00 Per Share Nor Less than $34.00 Per Share THE OFFER, PRORATION PERIOD AND WITHDRAWAL RIGHTS WILL EXPIRE AT 11:59 P.M., NEW YORK CITY TIME, ON JUNE 28, 2023, UNLESS THE OFFER IS EXTE

May 31, 2023 EX-99.(A)(1)(F)

Summary Advertisement, dated May 31, 2023.

Exhibit (a)(1)(F) This announcement is neither an offer to purchase nor a solicitation of an offer to sell Shares (as defined below).

May 31, 2023 EX-FILING FEES

Calculation of Filing Fees.

EX-FILING FEES 9 tm2316928d1ex-filingfees.htm EX-FILING FEES Exhibit 107 Calculation of Filing Fee Tables Schedule TO (Form Type) Oppenheimer Holdings Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Transaction Valuation Transaction Valuation Fee Rate Amount of Filing Fee Fees to Be Paid $ 30,000,000(1) 0.0001102 $ 3,306(2) Fees Previously Paid — Total Transaction Valuation $

May 31, 2023 EX-99.(A)(1)(D)

Letter to Brokers, Dealers, Commercial Banks, Trust Companies and Other Nominees, dated May 31, 2023.

 Exhibit (a)(1)(D) Offer to Purchase by Oppenheimer Holdings Inc. for an Aggregate Purchase Price of Up to $30,000,000 in Cash of Shares of its Class A non-voting common stock at a Purchase Price Not Greater than $40.00 Per Share Nor Less than $34.00 Per Share THE OFFER, PRORATION PERIOD AND WITHDRAWAL RIGHTS WILL EXPIRE AT 11:59 P.M., NEW YORK CITY TIME, ON JUNE 28, 2023, UNLESS THE OFFER IS EXTE

May 31, 2023 SC TO-I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) or 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 OPPENHEIMER HOLDINGS INC. (Name of Subject Company (Issuer) and Filin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) or 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 OPPENHEIMER HOLDINGS INC. (Name of Subject Company (Issuer) and Filing Person (Offeror)) Class A non-voting common stock, par value $0.001 per share (Title of Class of Securities) 671005106 (CUSIP Number of Class of Sec

May 31, 2023 EX-99.(A)(1)(A)

Offer to Purchase, dated May 31, 2023.

TABLE OF CONTENTS  Exhibit (a)(1)(A) Oppenheimer Holdings Inc. Offer to Purchase for an Aggregate Purchase Price of up to $30,000,000 in Cash of Shares of its Class A non-voting common stock at a Purchase Price Not Greater Than $40.00 per Share Nor Less Than $34.00 per Share THE OFFER, PRORATION PERIOD AND WITHDRAWAL RIGHTS WILL EXPIRE AT 11:59 P.M., NEW YORK CITY TIME, ON JUNE 28, 2023, UNLESS TH

May 31, 2023 EX-99.(A)(1)(B)

Letter of Transmittal.

 Exhibit (a)(1)(B) Letter of Transmittal To Tender Shares of Class A non-voting common stock of OPPENHEIMER HOLDINGS INC.

May 31, 2023 EX-99.(A)(5)

Press release announcing commencement of the Tender Offer, dated May 31, 2023.

Exhibit (a)(5) OPPENHEIMER HOLDINGS INC. ANNOUNCES CASH TENDER OFFER TO PURCHASE UP TO $30,000,000 MILLION OF ITS CLASS A NON-VOTING COMMON STOCK New York — May 31, 2023 — Oppenheimer Holdings Inc. (the “Company” or “Oppenheimer”) (NYSE: OPY) announced today the commencement of a modified “Dutch Auction” tender offer (the “Offer”) to purchase up to $30,000,000 million of its Class A non-voting com

May 9, 2023 8-K

As filed with the Securities and Exchange Commission on May 9, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of report

As filed with the Securities and Exchange Commission on May 9, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

May 9, 2023 EX-99.1

Annual Stockholders’ Meeting New York, NY May 8, 2023 Oppenheimer Holdings Inc. WELCOME to Oppenheimer’s 2023 Annual Stockholders’ Meeting May 8, 2023 2 Safe Harbor Statement This presentation and other written or oral statements made from time to ti

Annual Stockholders’ Meeting New York, NY May 8, 2023 Oppenheimer Holdings Inc. WELCOME to Oppenheimer’s 2023 Annual Stockholders’ Meeting May 8, 2023 2 Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Sec

May 1, 2023 EX-99.1

Oppenheimer Holdings Inc. First Quarter 2023 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may cont

opyq1-2023investorpresen Oppenheimer Holdings Inc. First Quarter 2023 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E

May 1, 2023 8-K

As filed with the Securities and Exchange Commission on May 1, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report

As filed with the Securities and Exchange Commission on May 1, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

April 28, 2023 EX-99.1

Oppenheimer Holdings Inc. Reports First Quarter 2023 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports First Quarter 2023 Earnings New York, April 28, 2023 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $14.6 million or $1.32 basic earnings per share for the first quarter of 2023, an increase of approximately 57.3%, compared with net income of $9.3 million or $0.75 basic earnings per share for the first q

April 28, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1

April 28, 2023 8-K

As filed with the Securities and Exchange Commission on April 28, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of repo

As filed with the Securities and Exchange Commission on April 28, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

March 17, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the registrant ☒ Filed by a party other than the registrant ☐ Check the appropriate box: ☐ Preliminary proxy statement ☐ Confidential, for use of

March 14, 2023 ARS

OPPENHEIMER HOLDINGS INC. Annual Report 2022 2022 2021 2020 2019 2018 In thousands except per share amounts and number of employees Gross revenue $1,110,941 $1,394,035 $1,198,667 $1,033,379 $958,154 Income before income taxes $45,554 $224,641 $169,00

a23-arx01annualreportbro OPPENHEIMER HOLDINGS INC. Annual Report 2022 2022 2021 2020 2019 2018 In thousands except per share amounts and number of employees Gross revenue $1,110,941 $1,394,035 $1,198,667 $1,033,379 $958,154 Income before income taxes $45,554 $224,641 $169,000 $74,912 $44,853 Net income $32,351 $158,964 $122,986 $52,953 $28,892 Basic earnings per share $2.77 $12.57 $9.73 $4.10 $2.1

March 3, 2023 EX-10.12

Oppenheimer & Co. Inc. Stock Appreciation Right Plan (previously filed as an exhibit to Form 10-K/A for the year ended December 31, 2022).

EX-10.12 4 a1012oppenheimercoincsto.htm EX-10.12 OPPENHEIMER HOLDINGS INC. STOCK APPRECIATION RIGHT PLAN 2 OPPENHEIMER HOLDINGS INC. STOCK APPRECIATION RIGHT PLAN 1. Plan Established Oppenheimer Holdings Inc. (“OPY”), hereby adopts this Stock Appreciation Right Plan (the ‘Plan”) on behalf of certain key employees of OPY and its subsidiary, Fahnestock & Co. Inc. (together, the “Company”) to be sele

March 3, 2023 EX-10.10

Offer Letter dated May 6, 2022 between Brad M. Watkins and Oppenheimer Holdings Inc. (previously filed as an exhibit to Form 10-K/A for the year ended December 31, 2022).

a1010offerletterdatedmay

March 3, 2023 EX-10.11

Lease dated October 15, 2018 between Chrysler East Building, L.L.C., Landlord, and Viner Finance Inc., Tenant, for premises at 666 Third Avenue, New York, New York (filed herewith).

a1011leasedatedoctober15 INGRAM YUZEK - GAINEN * CARROLL - BERTOLOTTI ¦ LLP October 16, 2018 Amol K.

March 3, 2023 10-K/A

For the fiscal year ended December 31, 2022

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 OMB APPROVAL OMB Number: 3235-0063 Expires: May 31, 2025 Estimated average burden hours per response . . . 2,255.26 FORM 10-K/A AMENDMENT NO. 1 (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR o TRANSITION REPORT PURSUANT TO SECTION

February 28, 2023 EX-21

Subsidiaries of the registrant

EXHIBIT 21 Subsidiaries of Oppenheimer Holdings Inc. As of December 31, 2022 Pursuant to Item 601(b)(21)(ii) of Regulation S-K, the names of certain other subsidiaries of Oppenheimer are omitted because, considered in the aggregate as a single subsidiary, they would not constitute a "significant subsidiary" as that term is defined in Rule 1-02(w) of Regulation S-X under the Securities Exchange Act

February 28, 2023 10-K

For the fiscal year ended December 31, 2022

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 OMB APPROVAL OMB Number: 3235-0063 Expires: May 31, 2025 Estimated average burden hours per response . . . 2,255.26 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR o TRANSITION REPORT PURSUANT TO SECTION

February 28, 2023 EX-22

Subsidiary Guarantors and Issuers of Registered Senior Secured Notes

Exhibit 22 Subsidiary Guarantors and Issuers of Registered Senior Secured Notes Oppenheimer Holdings, Inc.

January 30, 2023 EX-99.1

Oppenheimer Holdings Inc. Fourth Quarter and Full Year 2022 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “com

Oppenheimer Holdings Inc. Fourth Quarter and Full Year 2022 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Se

January 30, 2023 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on January 30, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

January 30, 2023 8-K

Other Events

As filed with the Securities and Exchange Commission on January 30, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

January 27, 2023 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on January 27, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

January 27, 2023 EX-99.1

Oppenheimer Holdings Inc. Reports Fourth Quarter and Full Year 2022 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Fourth Quarter and Full Year 2022 Earnings New York, January 27, 2023 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $22.4 million or $2.04 basic earnings per share for the fourth quarter of 2022 compared with net income of $62.9 million or $4.99 basic earnings per share for the fourth quarter of 2021. R

December 14, 2022 8-K

Financial Statements and Exhibits, Other Events

As filed with the Securities and Exchange Commission on December 14, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

October 31, 2022 EX-99.1

Oppenheimer Holdings Inc. Third Quarter 2022 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer” or the “company”) may cont

Oppenheimer Holdings Inc. Third Quarter 2022 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. ("Oppenheimer? or the ?company?) may contain ?forward-looking statements? within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchan

October 31, 2022 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on October 31, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

October 28, 2022 EX-99.1

Oppenheimer Holdings Inc. Reports Third Quarter 2022 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Third Quarter 2022 Earnings New York, October 28, 2022 ? Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $4.5 million or $0.40 basic earnings per share for the third quarter of 2022, compared with net income of $26.3 million or $2.07 basic earnings per share for the third quarter of 2021. Revenue for the th

October 28, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Numb

October 28, 2022 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on October 28, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

September 7, 2022 8-K

Other Events

As filed with the Securities and Exchange Commission on September 7, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

August 2, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

As filed with the Securities and Exchange Commission on August 2, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

August 1, 2022 EX-99.1

Oppenheimer Holdings Inc. Second Quarter 2022 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-loo

Oppenheimer Holdings Inc. Second Quarter 2022 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the ?company?) may contain ?forward-looking statements? within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934,

August 1, 2022 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on August 1, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 29, 2022 8-K

Financial Statements and Exhibits, Other Events

As filed with the Securities and Exchange Commission on July 29, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 29, 2022 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on July 29, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 29, 2022 EX-99.1

Oppenheimer Holdings Inc. Reports Second Quarter 2022 Earnings

EX-99.1 2 ex991-20228xkq2pressrelease.htm EX-99.1 Exhibit 99.1 Oppenheimer Holdings Inc. Reports Second Quarter 2022 Earnings New York, July 29, 2022 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported a net loss of $3.9 million or $(0.32) basic earnings per share for the second quarter of 2022, compared with net income of $31.2 million or $2.46 basic earnings per shar

July 29, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1-

June 16, 2022 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K

11-K 1 oppenheimer401k-2021fs.htm 11-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K (Mark One): ☒ ANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the fiscal year ended December 31, 2021 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the transition period from to Commission File Nu

May 24, 2022 8-K

Financial Statements and Exhibits, Other Events

As filed with the Securities and Exchange Commission on May 24, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

May 10, 2022 EX-99.1

Annual Stockholders’ Meeting New York, NY May 9, 2022 Oppenheimer Holdings Inc. WELCOME to Oppenheimer’s 2022 Annual Stockholders’ Meeting May 9, 2022 Safe Harbor Statement 3 This presentation and other written or oral statements made from time to ti

Annual Stockholders? Meeting New York, NY May 9, 2022 Oppenheimer Holdings Inc. WELCOME to Oppenheimer?s 2022 Annual Stockholders? Meeting May 9, 2022 Safe Harbor Statement 3 This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the ?company?) may contain ?forward-looking statements? within the meaning of Section 27A of the S

May 10, 2022 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on May 10, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

May 2, 2022 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on May 2, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

May 2, 2022 EX-99.1

Oppenheimer Holdings Inc. First Quarter 2022 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-look

Oppenheimer Holdings Inc. First Quarter 2022 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the ?company?) may contain ?forward-looking statements? within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, a

April 29, 2022 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on April 29, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

April 29, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1

April 29, 2022 EX-99.1

Oppenheimer Holdings Inc. Reports First Quarter 2022 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports First Quarter 2022 Earnings New York, April 29, 2022 ? Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $9.3 million or $0.75 basic earnings per share for the first quarter of 2022, a decrease of approximately 76.0%, compared with net income of $38.7 million or $3.07 basic earnings per share for the first qu

March 18, 2022 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the registrant?? Filed by a party other than the registrant ? Check the appropriate box: ? Preliminary proxy statement ? ? Confidential, for us

February 28, 2022 10-K

As filed with the U.S. Securities and Exchange Commission on February 28, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-K

Table of Contents As filed with the U.S. Securities and Exchange Commission on February 28, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHA

February 28, 2022 EX-21

Subsidiaries of the registrant (filed herewith).

EXHIBIT 21 Subsidiaries of Oppenheimer Holdings Inc. As of December 31, 2021 Pursuant to Item 601(b)(21)(ii) of Regulation S-K, the names of certain other subsidiaries of Oppenheimer are omitted because, considered in the aggregate as a single subsidiary, they would not constitute a "significant subsidiary" as that term is defined in Rule 1-02(w) of Regulation S-X under the Securities Exchange Act

February 28, 2022 EX-22

Subsidiary Guarantors and Issuers of Registered Senior Secured Notes (filed herewith).

Exhibit 22 Subsidiary Guarantors and Issuers of Registered Senior Secured Notes Oppenheimer Holdings, Inc.

February 25, 2022 8-K

Current Report

As filed with the Securities and Exchange Commission on February 25, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

February 10, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

As filed with the Securities and Exchange Commission on February 7, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

January 31, 2022 EX-99.1

Oppenheimer Holdings Inc. Fourth Quarter and Full Year 2021 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contai

Oppenheimer Holdings Inc. Fourth Quarter and Full Year 2021 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the ?company?) may contain ?forward-looking statements? within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange

January 31, 2022 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on January 31, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

January 28, 2022 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on January 28, 2022 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

January 28, 2022 EX-99.1

Oppenheimer Holdings Inc. Reports Fourth Quarter and Record Full Year 2021 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Fourth Quarter and Record Full Year 2021 Earnings New York, January 28, 2022 ? Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $62.9 million or $4.99 basic earnings per share for the fourth quarter of 2021 compared with net income of $81.9 million or $6.56 basic earnings per share for the fourth quarter of

December 20, 2021 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

As filed with the Securities and Exchange Commission on December 20, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

December 20, 2021 EX-99.1

Exhibit 99.1 OPPENHEIMER & CO. INC. INVESTMENT BANKING AND CAPITAL MARKETS DEFERRED COMPENSATION PLAN (Effective December 15, 2021) 1. Purpose of the Plan. The purpose of this Oppenheimer & Co. Inc. Investment Banking and Capital Markets Deferred Com

Exhibit 99.1 OPPENHEIMER & CO. INC. INVESTMENT BANKING AND CAPITAL MARKETS DEFERRED COMPENSATION PLAN (Effective December 15, 2021) 1. Purpose of the Plan. The purpose of this Oppenheimer & Co. Inc. Investment Banking and Capital Markets Deferred Compensation Plan (effective December 15, 2021) (the ?Plan?) is to enhance the overall effectiveness of the Company?s compensation program by providing a

December 14, 2021 8-K

Current Report

As filed with the Securities and Exchange Commission on December 14, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

December 14, 2021 EX-99.1

OPPENHEIMER HOLDINGS INC. DECLARES SPECIAL DIVIDEND

Exhibit 99.1 OPPENHEIMER HOLDINGS INC. DECLARES SPECIAL DIVIDEND New York, December 14, 2021 - Oppenheimer Holdings Inc. (?NYSE: OPY?) (the ?Company? or ?Firm) today announced that its Board of Directors has declared a special cash dividend on the Company?s Class A non-voting and Class B voting common stock of $1.00 per share, payable December 31, 2021, to shareholders of record at the close of bu

November 1, 2021 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on November 1, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

November 1, 2021 EX-99.1

Oppenheimer Holdings Inc. Third Quarter 2021 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-look

Oppenheimer Holdings Inc. Third Quarter 2021 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the ?company?) may contain ?forward-looking statements? within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, a

October 29, 2021 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on October 29, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

October 29, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Numb

October 29, 2021 EX-99.1

Oppenheimer Holdings Inc. Reports Third Quarter 2021 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Third Quarter 2021 Earnings New York, October 29, 2021 ? Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $26.3 million or $2.07 basic earnings per share for the third quarter of 2021, an increase of 67.8%, compared with net income of $15.6 million or $1.25 basic earnings per share for the third quarter of 2

September 23, 2021 SC 13G/A

OPY / Oppenheimer Holdings Inc. / PROPP MORRIS - SCHEDULE 13G AMENDMENT Passive Investment

OMB APPROVAL UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 OMB Number:3235-0145 Expires:Febuary 28, 2009 Estimated average burden hours per response ....10.4 SCHEDULE 13G/A Under the Securities and Exchange Act of 1934 (Amendment No. 1 )* Oppenheimer Holdings Inc. (Name of Issuer) Class A Common Shares (Title of Class of Securities) 683797104 (CUSIP Number) June 21, 2021

August 2, 2021 8-K/A

Current Report

As filed with the Securities and Exchange Commission on August 2, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

August 2, 2021 EX-99.1

Oppenheimer Holdings Inc. Second Quarter 2021 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-loo

Oppenheimer Holdings Inc. Second Quarter 2021 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the ?company?) may contain ?forward-looking statements? within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934,

July 30, 2021 EX-99.1

Oppenheimer Holdings Inc. Second Quarter 2021 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-loo

Oppenheimer Holdings Inc. Second Quarter 2021 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the ?company?) may contain ?forward-looking statements? within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934,

July 30, 2021 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on July 30, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 29, 2021 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1-

July 29, 2021 EX-99.1

Oppenheimer Holdings Inc. Reports Second Quarter 2021 Earnings and Announces Increase in the Quarterly Dividend

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Second Quarter 2021 Earnings and Announces Increase in the Quarterly Dividend New York, July 29, 2021 ? Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $31.2 million or $2.46 basic earnings per share for the second quarter of 2021, an increase of 76.5%, compared with net income of $17.6 million or $1.40 bas

July 29, 2021 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on July 29, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

June 25, 2021 SC 13G

OPY / Oppenheimer Holdings Inc. / PROPP MORRIS - SCHEDULE 13G Passive Investment

OMB APPROVAL UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 OMB Number:3235-0145 Expires:Febuary 28, 2009 Estimated average burden hours per response ....10.4 SCHEDULE 13G Under the Securities and Exchange Act of 1934 (Amendment No. )* Oppenheimer Holdings Inc. (Name of Issuer) Class A Common Shares (Title of Class of Securities) 683797104 (CUSIP Number) June 21, 2021 (Dat

June 21, 2021 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 11-K (Mark One): ☒ ANNUAL REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the fiscal year ended December 31, 2020 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934. For the transition period from to Commission File Number 8-04077 A. Full title of the plan

May 11, 2021 EX-99.1

Annual Stockholders’ Meeting: Virtual New York, NY May 10, 2021 Oppenheimer Holdings Inc. WELCOME to Oppenheimer’s 2021 Annual Stockholders’ Meeting May 10, 2021 Safe Harbor Statement 3 This presentation and other written or oral statements made from

Annual Stockholders? Meeting: Virtual New York, NY May 10, 2021 Oppenheimer Holdings Inc.

May 11, 2021 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on May 11, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

May 3, 2021 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on May 3, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

May 3, 2021 EX-99.1

First Quarter 2021 Investor Update Oppenheimer Holdings Inc. Safe Harbor Statement 2 This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-lo

First Quarter 2021 Investor Update Oppenheimer Holdings Inc. Safe Harbor Statement 2 This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the ?company?) may contain ?forward-looking statements? within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934,

April 30, 2021 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1

April 30, 2021 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on April 30, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

April 30, 2021 EX-99.1

Oppenheimer Holdings Inc. Reports First Quarter 2021 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports First Quarter 2021 Earnings New York, April 30, 2021 ? Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $38.7 million or $3.07 basic earnings per share for the first quarter of 2021, an increase of approximately 400%, compared with net income of $7.8 million or $0.61 basic earnings per share for the first qu

March 19, 2021 DEF 14A

- DEF 14A

QuickLinks - Click here to rapidly navigate through this document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

March 1, 2021 10-K

Annual Report - 10-K

Table of Contents As filed with the U.S. Securities and Exchange Commission on March 1, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE

March 1, 2021 EX-3.2

aws of Oppenheimer Holdings Inc. (filed herewith)

A/72840460.7 Exhibit 3.2 OPPENHEIMER HOLDINGS INC. BY-LAWS, as amended through February 25, 2021 ARTICLE I General 1.1Offices. The registered office of Oppenheimer Holdings Inc. (the ?Company?) shall be in the City of Wilmington, County of New Castle, State of Delaware. The Company may also have offices at such other places both within and without the State of Delaware as the Board of Directors ma

March 1, 2021 EX-22

Subsidiary Guarantors and Issuers of Registered Senior Secured Notes

Exhibit 22 Subsidiary Guarantors and Issuers of Registered Senior Secured Notes Oppenheimer Holdings, Inc.

March 1, 2021 EX-21

Subsidiaries of the registrant (filed herewith).

EXHIBIT 21 Subsidiaries of Oppenheimer Holdings Inc. As of December 31, 2020 Pursuant to Item 601(b)(21)(ii) of Regulation S-K, the names of certain other subsidiaries of Oppenheimer are omitted because, considered in the aggregate as a single subsidiary, they would not constitute a "significant subsidiary" as that term is defined in Rule 1-02(w) of Regulation S-X under the Securities Exchange Act

February 2, 2021 EX-99.1

Fourth Quarter and Full Year 2020 Investor Update Oppenheimer Holdings Inc. Safe Harbor Statement 2 This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may cont

a4q-20investorxpresenta Fourth Quarter and Full Year 2020 Investor Update Oppenheimer Holdings Inc.

February 2, 2021 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on February 2, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

January 29, 2021 EX-99.1

Oppenheimer Holdings Inc. Reports Fourth Quarter and Full Year 2020 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Fourth Quarter and Full Year 2020 Earnings New York, January 29, 2021 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $81.9 million or $6.56 basic earnings per share for the fourth quarter of 2020 compared with net income of $25.4 million or $1.99 basic earnings per share for the fourth quarter of 2019. R

January 29, 2021 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on January 29, 2021 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

December 10, 2020 8-K

Current Report

As filed with the Securities and Exchange Commission on December 09, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

December 10, 2020 EX-99.1

OPPENHEIMER HOLDINGS INC. Declares Special Dividend

Exhibit 99.1 OPPENHEIMER HOLDINGS INC. Declares Special Dividend December 9, 2020. New York, NY. Oppenheimer Holdings Inc. (?OPY?) today announced that its Board of Directors has declared a special cash dividend on OPY Class A non-voting and Class B voting common stock of $1.00 per share, payable December 30, 2020, to shareholders of record as of the close of business on December 23, 2020. The agg

November 25, 2020 424B3

OPPENHEIMER HOLDINGS INC. $125,000,000 5.50% Senior Secured Notes due 2025

Filed Pursuant to Rule 424(b)(3) Registration No. 333-249433 PROSPECTUS OPPENHEIMER HOLDINGS INC. $125,000,000 5.50% Senior Secured Notes due 2025 The notes bear interest at the rate of 5.50% per year. Interest on the notes is payable on October 1 and April 1 of each year, beginning on April 1, 2021. The notes mature on October 1, 2025. We may redeem any of the notes beginning on October 1, 2022.

November 24, 2020 CORRESP

-

Oppenheimer Holdings Inc. 85 Broad Street New York, New York 10004 November 24, 2020 VIA EDGAR AND FACSIMILE Securities and Exchange Commission Division of Corporation Finance 100 F St., N.E. Washington, D.C. 20549 Attn: Sonia Bednarowski Re: Oppenheimer Holdings Inc. Registration Statement on Form S-3 File No. 333-249433 Ladies and Gentlemen: Pursuant to Rule 461(a) under the Securities Act of 19

November 24, 2020 DEL AM

- DEL AM

Oppenheimer Holdings Inc. 85 Broad Street New York, New York 10004 November 24, 2020 VIA EDGAR AND FACSIMILE Securities and Exchange Commission Division of Corporation Finance 100 F St., N.E. Washington, D.C. 20549 Attn: Sonia Bednarowski Re: Oppenheimer Holdings Inc. Registration Statement on Form S-3 File No. 333-249433 Ladies and Gentlemen: Reference is made to the Registration Statement on For

November 24, 2020 S-3/A

- S-3/A

As filed with the Securities and Exchange Commission on November 24, 2020. Registration No. 333-249433 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 1 to FORM S-3 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 OPPENHEIMER HOLDINGS INC. and the Subsidiary Guarantors listed below (Exact name of registrant as specified in its charter) Delaware (State o

November 24, 2020 S-3/A

- FORM S-3/A

As filed with the Securities and Exchange Commission on November 24, 2020. Registration No. 333-249433 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 2 to FORM S-3 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 OPPENHEIMER HOLDINGS INC. and the Subsidiary Guarantors listed below (Exact name of registrant as specified in its charter) Delaware (State o

November 19, 2020 EX-99.1

OPPENHEIMER HOLDINGS INC. EXTENDS EXCHANGE OFFER

Exhibit 99.1 OPPENHEIMER HOLDINGS INC. EXTENDS EXCHANGE OFFER November 19, 2020. New York, NY. Oppenheimer Holdings Inc. (“OPY”) today announced that it has extended its offer to the holders of the $125.0 million aggregate principal amount of its 5.50% Senior Secured Notes due 2025, issued September 22, 2020, to exchange such notes for a like principal amount of notes with identical terms other th

November 19, 2020 8-K

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of report (Date of earliest event reported): November 19, 2020 OPPENHEIMER HOLDINGS INC. (Exact Name of Registrant as Specified in Charter) Commission File Number 1-12043 Delaware 98-0080034 (State or other jurisdiction of (I.R.

October 30, 2020 8-K

Regulation FD Disclosure - 8-K

As filed with the Securities and Exchange Commission on October 30, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

October 30, 2020 EX-99.1

Oppenheimer Holdings Inc. Third Quarter 2020 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-look

a3q-20investorxpresenta Oppenheimer Holdings Inc. Third Quarter 2020 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities

October 29, 2020 EX-99.1

Oppenheimer Holdings Inc. Reports Third Quarter 2020 Earnings

Exhibit 99.1 Oppenheimer Holdings Inc. Reports Third Quarter 2020 Earnings New York, October 29, 2020 – Oppenheimer Holdings Inc. (NYSE: OPY) (the "Company" or "Firm") today reported net income of $15.6 million or $1.25 basic earnings per share for the third quarter of 2020 compared with net income of $3.9 million or $0.31 basic earnings per share for the third quarter of 2019. Revenue for the thi

October 29, 2020 8-K

Results of Operations and Financial Condition - 8-K

As filed with the Securities and Exchange Commission on October 29, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

October 29, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Numb

October 20, 2020 424B3

$125,000,000 OPPENHEIMER HOLDINGS INC. EXCHANGE OFFER FOR 5.50% SENIOR SECURED NOTES DUE 2025

Filed pursuant to Rule 424(b)(3) Registration Nos. 333-249423 and 333-249423-01 and 333-249423-02 PROSPECTUS $125,000,000 OPPENHEIMER HOLDINGS INC. EXCHANGE OFFER FOR 5.50% SENIOR SECURED NOTES DUE 2025 Offer to exchange $125.0 million aggregate principal amount of 5.50% Senior Secured Notes due 2025 (which we refer to as the old notes) for $125.0 million aggregate principal amount of 5.50% Senior

October 16, 2020 CORRESP

Oppenheimer Holdings Inc. 85 Broad Street New York, New York 10004

Oppenheimer Holdings Inc. 85 Broad Street New York, New York 10004 October 16, 2020 VIA EDGAR AND FACSIMILE Securities and Exchange Commission Division of Corporation Finance 100 F St., N.E. Washington, D.C. 20549 Attn: Sonia Bednarowski Re: Oppenheimer Holdings Inc. Registration Statement on Form S-4 File No. 333-249423 Ladies and Gentlemen: Pursuant to Rule 461(a) under the Securities Act of 193

October 9, 2020 S-3

Power of Attorney.

As filed with the Securities and Exchange Commission on October 9, 2020. Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-3 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 OPPENHEIMER HOLDINGS INC. and the Subsidiary Guarantors listed below (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of inc

October 9, 2020 CORRESP

[Signature Page to Exxon Capital Letter]

October 9, 2020 VIA EDGAR Division of Corporation Finance U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Oppenheimer Holdings Inc. Registration Statement on Form S-4 (File No. 333-249423) Ladies and Gentlemen: Oppenheimer Holdings Inc. (the ?Company?), the primary obligor under its 5.50% Senior Secured Notes due 2025 (the ?Old Notes?) and each of the guaranto

October 9, 2020 S-4

- FORM S-4

As filed with the Securities and Exchange Commission on October 9, 2020. Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-4 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 OPPENHEIMER HOLDINGS INC. (Exact name of registrant as specified in its charter) Delaware 6211 98-0080034 (State or other jurisdiction of incorporation or organization)

October 9, 2020 EX-25.1

Form T-1 Statement of Eligibility under the Trust Indenture Act of 1939, as amended, of The Bank of New York Mellon Trust Company, N.A., as trustee under indenture, dated as of September 22, 2020.

Exhibit 25.1 = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CORPORATION DESIGNATED TO ACT AS TRUSTEE CHECK IF AN APPLICATION TO DETERMINE ELIG

October 9, 2020 EX-25.1

Form T-1 Statement of Eligibility under the Trust Indenture Act of 1939, as amended, of The Bank of New York Mellon Trust Company, N.A., as trustee under indenture, dated as of September 22, 2020.

Exhibit 25.1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM T-1 STATEMENT OF ELIGIBILITY UNDER THE TRUST INDENTURE ACT OF 1939 OF A CORPORATION DESIGNATED TO ACT AS TRUSTEE CHECK IF AN APPLICATION TO DETERMINE ELIGIBILITY OF A TRUSTEE PURSUANT TO SECTION 305(b)(2) ¨ THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. (Exact name of trustee as specified in its charter) (Ju

October 9, 2020 EX-99.1

Form of Letter of Transmittal.

Exhibit 99.1 letter of transmittal OPPENHEIMER HOLDINGS INC. Offer for All Outstanding 5.50% Senior SECURED Notes Due 2025 in Exchange for 5.50% Senior Secured Notes Due 2025 Which Have Been Registered Under the Securities Act of 1933, as Amended, Pursuant to the Prospectus Dated , 2020 The Exchange Offer will expire at 5:00 p.m. New York City time, on , 2020 (the “EXPIRATION DATE”), unless extend

October 9, 2020 EX-99.3

Form of Letter to Brokers, Dealers.

Exhibit 99.3 OPPENHEIMER HOLDINGS INC. OFFER FOR ALL OUTSTANDING 5.50% SENIOR secured NOTES DUE 2025 IN EXCHANGE FOR 5.50% SENIOR secured NOTES DUE 2025 WHICH HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED , 2020 To Brokers, Dealers, Commercial Banks, Trust Companies and Other Nominees: Oppenheimer Holdings Inc. (“Oppenheimer”) is offering, upon and subject to the terms and cond

October 9, 2020 EX-99.2

Form of Letter to Clients.

Exhibit 99.2 OPPENHEIMER HOLDINGS InC. OFFER FOR ALL OUTSTANDING 5.50% SENIOR SECURED NOTES DUE 2025 IN EXCHANGE FOR 5.50% SENIOR SECURED NOTES DUE 2025 WHICH HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED , 2020 To our Clients: Enclosed for your consideration is a prospectus, dated , 2020 (the “Prospectus”), relating to the offer (the “Exchange Offer”) of Oppenheimer Holdings I

September 22, 2020 EX-10.2

Registration Rights Agreement, dated September 22, 2020, by and among Oppenheimer Holdings Inc., a Delaware corporation, E.A. Viner International Co., a Delaware corporation, Viner Finance Inc., a Delaware corporation and Oppenheimer Co. & Inc., as the Initial Purchaser (previously filed as an exhibit to Form 8-K dated September 22, 2020 and incorporated herein by reference).

Exhibit 10.2 Execution Version REGISTRATION RIGHTS AGREEMENT This REGISTRATION RIGHTS AGREEMENT dated September 22, 2020 (the “Agreement”) is entered into by and among Oppenheimer Holdings Inc, a Delaware corporation (the “Company”), E.A. Viner International Co., a Delaware corporation (“Viner”), Viner Finance Inc., a Delaware Corporation (“Viner Finance” and together with Viner, the “Guarantors”)

September 22, 2020 8-K

As filed with the Securities and Exchange Commission on September 22, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of

As filed with the Securities and Exchange Commission on September 22, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

September 22, 2020 EX-4.1

Indenture, dated as of September 22, 2020, by and among Oppenheimer Holdings Inc., the subsidiary guarantors party thereto, The Bank of New York Mellon Trust Company, N.A., as Trustee and as Collateral Agent (previously filed as an exhibit to Form 8-K dated September 22, 2020 and incorporated herein by reference).

Exhibit 4.1 EXECUTION VERSION INDENTURE Dated as of September 22, 2020 Among OPPENHEIMER HOLDINGS INC., THE SUBSIDIARY GUARANTORS NAMED ON THE SIGNATURE PAGES HERETO, THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., as Trustee and THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., as Collateral Agent 5.50% SENIOR SECURED NOTES DUE 2025 CROSS-REFERENCE TABLE* Trust Indenture Act Section Indenture Sec

September 22, 2020 EX-10.1

Security Agreement by and among Oppenheimer Holdings Inc., as grantor, and each other grantor from time to time party thereto and the Bank of New York Mellon Trust Company, N.A., as Collateral Agent dated as of September 22, 2020 (previously filed as exhibit 10.1 to Form 8-K dated September 22, 2020).

Exhibit 10.1 EXECUTION VERSION SECURITY AGREEMENT by and among OPPENHEIMER HOLDINGS INC. as Grantor, and EACH OTHER GRANTOR FROM TIME TO TIME PARTY HERETO and THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. as Collateral Agent. Dated as of September 22, 2020 TABLE OF AUTHORITIES PAGE ARTICLE 1 DEFINITIONS; GRANT OF SECURITY Section 1.01. General Definitions 1 Section 1.02. Definitions; Interpretat

September 17, 2020 8-K

Financial Statements and Exhibits, Other Events - 8-K

As filed with the Securities and Exchange Commission on September 17, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

September 17, 2020 EX-99.1

OPPENHEIMER ANNOUNCES PRICING OF SENIOR SECURED NOTES OFFERING

Exhibit 99.1 OPPENHEIMER ANNOUNCES PRICING OF SENIOR SECURED NOTES OFFERING September 17, 2020, New York, NY. Oppenheimer Holdings Inc. (“OPY” or the “Company”) announced today that it priced $125 million aggregate principal amount of 5.50% senior secured notes due 2025 (the “Notes”) at an initial offering price of 100% of the principal amount in connection with its previously announced private of

September 10, 2020 8-K

Financial Statements and Exhibits, Other Events - 8-K

As filed with the Securities and Exchange Commission on September 10, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

September 10, 2020 EX-99.1

OPPENHEIMER ANNOUNCES PROPOSED SENIOR SECURED NOTES OFFERING

Exhibit 99.1 OPPENHEIMER ANNOUNCES PROPOSED SENIOR SECURED NOTES OFFERING September 10, 2020. New York, NY. Oppenheimer Holdings Inc. (“OPY” or “the Company”) announced today that it is proposing to issue $125 million aggregate principal amount of senior secured notes due 2025 (the “Notes”) in a private offering that is exempt from the registration requirements of the Securities Act of 1933, as am

August 28, 2020 8-K

Other Events - 8-K

As filed with the Securities and Exchange Commission on August 28, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 31, 2020 EX-99.1

OPPENHEIMER HOLDINGS INC. Second Quarter 2020 Investor Update SAFE HARBOR STATEMENT This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward‐loo

a2q20investorpresentatio OPPENHEIMER HOLDINGS INC. Second Quarter 2020 Investor Update SAFE HARBOR STATEMENT This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward‐looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securiti

July 31, 2020 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on July 31, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 30, 2020 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on July 30, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 30, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2020 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1-

June 16, 2020 11-K

- 11-K

Oppenheimer & Co. Inc. 401(k) Plan Financial Report December 31, 2019 Oppenheimer & Co. Inc. 401(k) Plan Contents Report Letter 1 Statement of Net Assets Available for Plan Benefits 3 Statement of Changes in Net Assets Available for Plan Benefits 4 Notes to Financial Statements 5-10 Schedule of Assets Held at End of Year Schedule 1 Report of Independent Registered Public Accounting Firm To the Pla

May 15, 2020 8-K

Current Report

8-K 1 opy8-ksharerepurcprogr51520.htm 8-K As filed with the Securities and Exchange Commission on May 15, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): May 15, 2020 OPPENHEIMER HOLDINGS INC. (Exact Name of Registrant as Spec

May 12, 2020 S-8

- S-8

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933, AS AMENDED OPPENHEIMER HOLDINGS INC. (Exact name of Registrant as Specified in its Charter) Delaware 98-0080034 (State or Other Jurisdiction of (I.R.S. Employer Incorporation or Organization) Identification No.) 85 Broad Street New York, New York 10004 (Address,

May 12, 2020 EX-23.A1

Consent of Deloitte & Touche LLP

EXHIBIT 23(a)(1) CONSENT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM We consent to the incorporation by reference in this Registration Statement on Form S-8 of our reports relating to the consolidated financial statements of Oppenheimer Holdings Inc.

May 12, 2020 EX-99.1

OPPENHEIMER HOLDINGS INC. Annual Stockholders’ Meeting: Virtual New York, NY May 11, 2020 WELCOME to Oppenheimer’s 2020 Annual Stockholders’ Meeting May 11, 2020 SAFE HARBOR STATEMENT This presentation and other written or oral statements made from t

opyshareholdermeeting511 OPPENHEIMER HOLDINGS INC. Annual Stockholders’ Meeting: Virtual New York, NY May 11, 2020 WELCOME to Oppenheimer’s 2020 Annual Stockholders’ Meeting May 11, 2020 SAFE HARBOR STATEMENT This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward‐looking statements” within t

May 12, 2020 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on May 12, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

May 12, 2020 EX-23.B

Consent of Schnader Harrison Segal & Lewis LLP (included in Exhibit 5).

EXHIBIT 23(b) THE CONSENT OF SCHNADER HARRISON SEGAL & LEWIS LLP IS INCLUDED IN EXHIBIT 5 CONTAINED HEREIN. 1

May 12, 2020 EX-24

Power of Attorney (included on the signature pages of this registration statement).

EXHIBIT 24 POWER OF ATTORNEY Each person whose signature appears below hereby constitutes and appoints Jeffrey J.

May 4, 2020 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on May 4, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

May 4, 2020 EX-99.1

OPPENHEIMER HOLDINGS INC. First Quarter 2020 Investor Update SAFE HARBOR STATEMENT This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward‐look

a1q20investorpresentatio OPPENHEIMER HOLDINGS INC. First Quarter 2020 Investor Update SAFE HARBOR STATEMENT This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward‐looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securitie

May 1, 2020 10-Q

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2020 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1

May 1, 2020 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on May 1, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

April 23, 2020 DEFA14A

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C.20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the registrant x Filed by a party other than the registrant ¨ Check the appropriate box: ¨ Preliminary proxy statement ¨ Confidential, for use of

March 20, 2020 DEF 14A

definitive proxy statement filed with the SEC on March 20, 2020

QuickLinks - Click here to rapidly navigate through this document UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

March 2, 2020 10-K

OPY / Oppenheimer Holdings Inc. 10-K - Annual Report - 10-K

Table of Contents As filed with the U.S. Securities and Exchange Commission on March 2, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2019 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE

March 2, 2020 EX-21.1

Subsidiaries of the Registrant (previously filed as an exhibit to Form 10-K for the year ended December 31, 2019 and incorporated herein by reference).

EXHIBIT 21 Subsidiaries of Oppenheimer Holdings Inc. As of December 31, 2019 Pursuant to Item 601(b)(21)(ii) of Regulation S-K, the names of certain other subsidiaries of Oppenheimer are omitted because, considered in the aggregate as a single subsidiary, they would not constitute a "significant subsidiary" as that term is defined in Rule 1-02(w) of Regulation S-X under the Securities Exchange Act

February 3, 2020 EX-99.1

OPPENHEIMER HOLDINGS INC. Fourth Quarter and Full Year 2019 Investor Update SAFE HARBOR STATEMENT This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contai

a4q19investorpresentatio OPPENHEIMER HOLDINGS INC. Fourth Quarter and Full Year 2019 Investor Update SAFE HARBOR STATEMENT This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E o

February 3, 2020 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on February 3, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

January 31, 2020 8-K

Results of Operations and Financial Condition

8-K 1 a20198-kq4pressrelease.htm 8-K As filed with the Securities and Exchange Commission on January 31, 2020 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): January 31, 2020 OPPENHEIMER HOLDINGS INC. (Exact name of registrant as s

October 28, 2019 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on October 28, 2019 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

October 28, 2019 EX-99

Oppenheimer Holdings Inc. Third Quarter 2019 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-look

a3q19investorpresentatio Oppenheimer Holdings Inc. Third Quarter 2019 Investor Update Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securitie

October 25, 2019 10-Q

OPY / Oppenheimer Holdings Inc. 10-Q - Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2019 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Numb

October 25, 2019 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on October 25, 2019 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

September 4, 2019 EX-99.1

Oppenheimer Holdings Inc. Investor Presentation – September 2019 Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward‐

a2q19investorpresentatio Oppenheimer Holdings Inc. Investor Presentation – September 2019 Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward‐looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Secur

September 4, 2019 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on September 4, 2019 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 29, 2019 EX-99.1

Oppenheimer Holdings Inc. Second Quarter Update – 2019 Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-looking st

a2q19investorpresentatio Oppenheimer Holdings Inc. Second Quarter Update – 2019 Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exch

July 29, 2019 8-K

Regulation FD Disclosure

8-K 1 opy8-kinvestorpresentation.htm 8-K As filed with the Securities and Exchange Commission on July 29, 2019 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of report (Date of earliest event reported): July 29, 2019 OPPENHEIMER HOLDINGS INC. (Exact name of registrant as spe

July 26, 2019 8-K

Results of Operations and Financial Condition

As filed with the Securities and Exchange Commission on July 26, 2019 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

July 26, 2019 10-Q

OPY / Oppenheimer Holdings Inc. 10-Q - Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2019 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 1-

June 20, 2019 11-K

OPY / Oppenheimer Holdings Inc. 11-K - - 11-K

Oppenheimer & Co. Inc. 401(k) Plan Financial Report December 31, 2018 Oppenheimer & Co. Inc. 401(k) Plan Contents Report Letter 1 Statement of Net Assets Available for Plan Benefits 3 Statement of Changes in Net Assets Available for Plan Benefits 4 Notes to Financial Statements 5-10 Schedule of Assets Held at End of Year Schedule 1 Report of Independent Registered Public Accounting Firm To the Pla

May 14, 2019 EX-99.1

Oppenheimer Holdings Inc. Annual Stockholders’ Meeting New York, NY May 13, 2019 WELCOME to Oppenheimer’s 2019 Annual Stockholders’ Meeting May 13, 2019 1 Safe Harbor Statement This presentation and other written or oral statements made from time to

opyshareholdermeeting513 Oppenheimer Holdings Inc. Annual Stockholders’ Meeting New York, NY May 13, 2019 WELCOME to Oppenheimer’s 2019 Annual Stockholders’ Meeting May 13, 2019 1 Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward-looking statements” within the mean

May 14, 2019 8-K

Regulation FD Disclosure

As filed with the Securities and Exchange Commission on May 14, 2019 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

April 29, 2019 8-K

Regulation FD Disclosure

8-K 1 opy8-kinvestorpresentation.htm 8-K As filed with the Securities and Exchange Commission on April 29, 2019 UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): April 29, 2019 OPPENHEIMER HOLDINGS INC. (Exact Name of Registrant as S

April 29, 2019 EX-99.1

Oppenheimer Holdings Inc. First Quarter Update – 2019 Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward‐looking sta

a1q19investorpresentatio Oppenheimer Holdings Inc. First Quarter Update – 2019 Safe Harbor Statement This presentation and other written or oral statements made from time to time by representatives of Oppenheimer Holdings Inc. (the “company”) may contain “forward‐looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Excha

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