OPPENHEIMER HOLDINGS INC. NOVEMBER 2015

Presented by: Robert Lowenthal Senior Managing Director, Chairman of Management Committee Jeffrey Alfano Executive Vice President & Chief Financial Officer 2 art II, “Item 7. Management’s ied in their entirety by reference to all such factors discussed in e to time by representatives of Oppenheimer Holdings Inc. (the ions – Factors Affecting ‘Forward-Looking Statements’” of our lude those factors discussed in P ’s forwarding-looking statements. These risks and uncertainties . In addition, important factors that could cause actual results to can be no assurance that the company has correctly or completely . These forward-looking statements may relate to such matters as siness. The company does not undertake any obligation to publicly on Reform Act of 1995 provides a safe harbor for forward-looking

TATEMENT nce, future revenues or earnings, business prospects, new products or services, anticipated market S

ARBOR

H

AFE This presentation and other written or oral statements made from tim “company”) “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, as amended anticipated financial performa performance and similar matters. The Private Securities Litigati statements. The company cautions that a variety of factors could cause the company’s anticipated results actual or results other to expectations expressed differ in materially the company from the include, but are not limited to, those risk factors discussed in Part I, “Item 1A. Risk Factors” of our Annual Report on Form 10-K for the fiscal year ended December 31, 2014 (the “2014 Annual Report”) differ materially from those in the forward-looking statements inc Discussion & Analysis of Financial Condition and Results of Operat 2014 Annual Report. Any forward-looking statements herein are qualif the 2014 Annual Report and the company’s other SEC filings. There identified and assessed all of the factors affecting the company’s bu or update any revise forward-looking statements. S 3 Banking covering rehabilitation and ~575 equity securities ~575 equity 91 offices in 24 91 states; 5 foreign jurisdictions Commercial Mortgage 40 senior research analysts and healthcare properties construction of multifamily construction of Provides high quality service for the acquisition, refinance, Quick Facts corporations +250 Institutional Capital Markets Sales Professionals institutions and services and capital markets products for 1,250+ Financial Advisors

S

U Under Management $23.7B Client Assets $79.6B Client Assets Oppenheimer is a leading investment and full-service Oppenheimer Under Administration tailored to individuals net worth investors, individuals, businesses and institutions. Private client services and unique financial objectives asset management solutions Note: Data as Note: 2015 of September 30, BOUT investment firm that provides and advice to high

A 4 Buy & Hold 2008 Oppenheimer acquires Capital CIBC U.S. Markets

Carolan & Co. Carolan 2003 of Michigan & Son Newhold’s WH BC Christopher Propp & Co. Propp Fahnestock & Co. acquires Fahnestock & Client Oppenheimer Private & Asset Management businesses from CIBC Co. Inc. Fahnestock & Co. changes Fahnestock & name its to Oppenheimer & First Acquisitions

1999 financial goals. Fahnestock Viner Holdings becomes listed on NYSE

1950 Oppenheimer & Co. Founded expertise and insight to meet the challenge of achieving their expertise Buetti Cannon Laidlaw Adams & Peck & Co. Reich

ERITAGE investors with the For over 130 necessary years, we have provided 1881 NY & SecForeign & Co. Josephthal Charter Prime Fahnestock & Co. Founded H WHERE WE OPERATE Oppenheimer serves clients from 91 offices located throughout the as well as select global money centers.

Seattle

Minneapolis Michigan

Boston Chicago New York Kansas City Pittsburgh Philadelphia Denver Cincinnati Baltimore St. Louis

Los Angeles Dallas San Diego 

International  New York Miami  Philadelphia 

 Hong Kong

5 6 Entrepreneurial Mindset Entrepreneurial Trusted Reputation Trusted Flexibility At Scale Flexibility At Heritage and Continuity clients. Client Focus Tailored Advice Open Architecture Proven Expertise

OMMITMENT

C and our clients' investment needs commitment to our Our tradition to deliver effective and innovative solutions to our to deliver tradition

UR experienced and dedicated professionals empower us in our proud us in our empower and dedicated professionals experienced O 7 Foreign Money Center et Investment Banks et Investment Capital Markets Boutiques Bulge Bracket Investment Banks Full Service / Mid-Mark Full Service /

NDUSTRY

I UR Boutiques Advisory

O 8 strategies Experienced ‐ ranked research Traditional and Traditional professionals lead Top customer engagement alternative investment investment alternative

S

U Full service capabilities capabilities stable profile Global distribution Global distribution Diversified business,

IFFERENTIATES investment bank. of a global, full-service capabilities Each of our business lines benefits from the dedicated, D senior-level commitment of a boutique combined with the combined commitment of a boutique senior-level

HAT

W 9 improve profitability.

TRATEGY S Refining operations and increasing pr oductivity within our core businesses increasing Refining operations and Developing new product offerings resources Adding the right recruiting and retaining top talent – shift from transaction to fee-based Focusing resources on secular accounts Seeking accretive acquisitions that fit our model . . . . .

ROWTH base and revenue streams, while also leveraging our operations to Oppenheimer is pursuing a number of initiatives to grow our client G 10 age age Banking ercial ercial Mortg (1) arkets Comm (2) Operating Operating Profit $529,777 $38.92 $26.29 $258,348 $18.91 $952,953 Wealth Management M Capital 5.0% 0.0% 15.0% 10.0% 35.0% 30.0% 25.0% 20.0% s at 10/29/15 Snapshot Book-value at 9/30/15 Share Price

ESULTS LTM Revenue 9/30/15 (‘000s) Tangible Book-value at 9/30/15 Book-value at Tangible

R 10/29/15 (‘000s) Cap at Market

UR nt and Asset nt Management business segment Shareholders' Equity at 9/30/15 (‘000s) 68% $641.8 ude allocations to Corporate – Other category – Other Corporate ude allocations to

O Wealth 29% $279.6 Capital Markets Management T Business Segment Results LTM September 30, 2015 Segment Results LTM Business

A

OOK Total Revenue: $953M Total Revenue: L

S ’

ET Wealth Management represents Private Clie Wealth Management Operating Profit as reported. Does not incl Does not as Operating Profit reported.

L 3% $30.6 (1) (2) Banking Mortgage Commercial 11 15 ‐ 15 ‐ 3Q LTM 3Q ($ thousands) Net Income/(Loss) Gross Revenue ($M)

ESULTS CONTINUED

R 2007 2008 2009 2010 2011 2012 2013 2014 $75,367 $75,367 $(20,770) $20,824 $38,532 $10,316 $(3,613) $25,061 $8,826 $7,792 2007 2007 2008 2009 2010 2011 2012 2013 2014 LTM ‐ $ $980 $960 $940 $920 $900 $880 $860 $840 $80,000 $60,000 $40,000 $20,000 Net Income Net $1,060 $1,040 $1,020 $1,000 $(20,000) $(40,000) $100,000

INANCIAL F 12 19% 5.4x 28% 24% $679.777 $529,777 $150,000 $2,854,252 $2,854,252 September 30, 2015 September U.S. Govt, Agency, & Sov Debt & Sov Debt Agency, Govt, U.S. Corporate debt MBS Municipals Convertible bonds Corporate equities Auction securities rate Ratios 72% Capital Structure $1,040M – 3Q-15 $1,040M –

30, 2015 9% Total Assets: Debt to Equity: ($ in thousands) Stockholders’ Equity: Long-Term Debt: Total Capitalization: Equity to Assets: Capitalization to Assets: Ratio: Gross Leverage Securities Inventory Composition 4% 5%

EPTEMBER 7% 2%

S % 1

TRUCTURE AS OF S

APITAL Straight-forward balance sheet Straight-forward balance 3 assets represent Level 4.1% of total assets (primarily ARS) Regulatory Net Capital of $143.4M Net Capital of $111.6M Regulatory Excess Long-term Debt Financing Secured Through 2018 Primarily a client-facing business (limited proprietary trading) High turnover of securities inventory thousand of $650 2014 VaR average No significant losses during crisis financial ratio consistent around 5x Gross leverage

C Conservative Risk Profile . Securities Trading ...... 13 1.5% 0.57 0.54 3Q-15 3Q-15 1.7% 0.65 0.62 2014 LTM 1.85 1.77 4.8% -0.27 -0.7% 2012 2013 -0.27 EPS - basic - basic EPS 0.76 2.0% 0.74 ROE 7.6% 2.89 2.77 EPS - diluted - diluted EPS 1.59 4.5% 1.55 Earnings per Share ($) -1.51 -1.51 -4.6% 2007 2008 2009 2010 2011 2012 2013 2014 LTM 5.70 18.3% 5.57 2007 2008 2009 2010 2011 1.00 1.00 8.0% 6.0% 7.00 2.0% 0.0% 3.00 4.0% 4.0% 5.00 5.00 6.00 2.00 0.00 4.00 4.00 -1.00 18.0% 18.0% 16.0% -6.0% 12.0% 12.0% -2.0% 10.0% 14.0% 14.0% -4.0% -2.00 20.0% 2.2% 3Q-15 $38.92 3Q-15 2.6% $38.71 $26.27 $26.29 4.3% 4.3% $38.77 $26.19 EASURES -0.1% $36.80 M $24.34 Book Value per Share per Share Book Value 2011 2012 2013 2014 1.9% $37.16 $24.47 6.6% $37.73 $24.32 Book Value 3.7% $20.87 INANCIAL $34.88 Pretax Margin (%) Pretax Margin F Tangible BV per share Tangible -4.0% $19.04 $33.38 2007 2008 2009 2010 2007 2008 2009 2010 2011 2012 2013 2014 LTM $21.07 13.9% $33.22

ELECT $15 $10 $35 $30 $25 $20 $45 $40 8.0% 6.0% 2.0% 0.0% 4.0% 4.0% 16.0% -6.0% 12.0% 12.0% S -2.0% 10.0% 14.0% 14.0% -4.0% 14 Technology Implementing new technology Implementing new to replace legacy systems that management support asset business Continue to develop new and new develop Continue to enhance existing applications across the firm Engaged additional vendors to with enhancing “Know assist Your Client” and AML procedures ˗ ˗ ˗ Compliance with new regulatory requirements Compliance Enhanced review of employment practices Purchase & development of technology development Purchase & applications . . .

OMPLIANCE

C Process Established committees and working groups to address new initiatives Enhanced policies and Developed new reports for management and compliance procedures ˗ ˗ ˗

EGULATORY

R address legal, compliance & regulatory matters. compliance & regulatory legal, address People Increased staffing of regulatory & compliance groups Appointment of qualified leadership Tone at the Top & Compliance Regime the Top & Compliance Tone at Structural and leadership changes Increased staffing in broker- dealer and investment advisory compliance departments New AML officer and increased staffing in AML department New Corporate Information Security Officer . . . ˗ ˗ ˗ ˗

NVESTING IN to has spent a significant amount of time and resources Oppenheimer I 15 $96.5 $91.4 $85.1 $72.0 $68.2 $35.9 Company ($M) $4.5

ATTER $5.3 Feb-08 2009 2010 2011 2012 2013 2014 Sept-15 ents totals $111.6M through September 30, 2015 $0.0 ements with the regulators held approximately ements $80.0 $60.0 $20.0 $40.0 $120.0 $100.0 and awards as of September 30, 2015 was $9.6M and Massachusetts Securities Division in Feb. 2010 Securities Division in Feb. Massachusetts ARS M 2008 with over $330B outstanding in market 2008 with over $330B outstanding $0.174 ARS Holdings $0.194 $0.24 DDRESS THE

A $0.30 $0.58 Client ($B) $0.85

ONTINUE TO $1.30

C

E $2.79 Feb-08 2009 2010 2011 2012 2013 2014 Sept-15 $78.5M of ARS as September 30, 2015 Commitments to purchase under legal settlements Eligible investors for future buybacks under the settl under the investors for future buybacks Eligible ARS purchased from clients under regulatory settlem purchased from clients ARS Auction Rate Securities failed in (“ARS”) Feb. Oppenheimer clients held $2.8B in Feb. 2008 with New York Settlement Attorney General and . . . . W . . $1.5 $1.0 $3.0 $2.5 $0.5 $2.0 $0.0 16 $38.4 3Q-15 $37.3 $35.5 Money Fund Sweep Program Sweep Program Fund Money $35.1

NVIRONMENT

E $33.8 Cash Sweep $37.7 Revenues ($M) Balances* ($M) Interest and Fee ATE

R $45.5 $89.7 2009 2009 2010 2011 2012 2013 2014 2015 Sept. Margin Interest FDIC Money Market Product 2007 2008 2009 2010 2011 2012 2013 2014 LTM $111.4 ‐ *Money market funds plus FDIC-insured bank deposits market funds plus FDIC-insured bank *Money

NTEREST I 9,000 8,000 7,000 6,000 5,000 4,000 3,000 2,000 1,000

ISING

A R

OR F

ELL

W Cash sweep balances Margin lending Rate (Auction Firm investments Securities) – – – Low interest rates have had significant impact on interest and fee revenues revenues Gross interest down approximately $74M annually since 2010 due to low interest rates sensitive Firm’s interest rate products: As of June 30, 2015, the Firm has consolidated its money market funds into the FDIC-insured bank deposits Market indicates 50-50 chance that the Federal Reserve will raise rates before year-end . . . OSITIONED . . P 17

PPENHEIMER Oppenheimer has a strong history Oppenheimer has a strong The firm has navigated through a difficult environment Our client assets are near all time highs Our business model is low risk and well diversified We are poised to benefit from a rising interest rate environment We are investing in our future and well-positioned for growth

O ......

HY

W APPENDIX 19 101.1 3Q-15 100.0 102.2 Asset Allocation Investment Manager Recommendations Portfolio Monitoring Consolidated Reporting Due Diligence 92.9      74.0 74.0 63.2 61.5 Wealth Management Services th Management Operating Profit* ($M) Planning Services Retirement Services Trust Services Estate and Succession Strategies Portfolio Analysis Personal Investment Policy 87.1 2007 2008 2009 2010 2011 2012 2013 2014 LTM       0.0 80.0 60.0 20.0 Weal 40.0 40.0 120.0 100.0 3Q-15

VERVIEW

O

ANAGEMENT

M 2007 2008 2009 2010 2011 2012 2013 2014 LTM

EALTH Wealth Management Revenue* ($M) - Wealth Management represents Private Client and Asset Management business segments Provide a full range of products and services to clients to meet their complex and evolving financial needs advice financial One-on-one personalized transfer Position business for generational of wealth Increased focus on mitigation of regulatory risk 100 700 300 500 800 600 200 400 W . . . . . *Segment revenue and operating profit as profit *Segment revenue and operating reported 20 79.6 23.7 87.3 25.9 84.6 25.3 80.3 20.9 76.0 18.6 73.2 18.8 66.0 16.4 48.1 Assets Under Management ($B) 12.5 62.3 2007 2008 2009 2010 2011 2012 2013 2014 3Q-15 Assets Under Administration ($B) 17.5 ) 2007 2008 2009 2010 2011 2012 2013 2014 3Q-15 0 10 5 0 70 30 50 80 60 90 20 40 15 10 30 25 100 20 61 ONTINUED to

(C 66 will 61 and systems platform 57 53 Vestmark programs 51

ANAGEMENT of portfolio managers who

M 45 to Oppenheimer series 36 50

EALTH 2007 2008 2009 2010 2011 2012 2013 2014 3Q-15 Client Assets per Financial Advisor ($M) Client Assets $61.2M of assets per advisor financial Increase in AUM comprised of asset appreciation and new assets assets Continued focus on shift in client fee-based programs Recent contract with consolidate advisory Identified are unique - 10 70 30 50 60 20 W 40 . . . . . 21 5% OIM 9% Other 11% Alternative Investments 100% 80% 60% 40% 20% 0% $23.7B 75% Advisory Fees % of Total Advisory Fees Traditional Distribution of AUM 3Q-15

) Total Commissions Management Advisory Fees and Commissions Management Advisory

ONTINUED

(C Advisory Fees - Asset Management Management - Asset Fees Advisory

ANAGEMENT 2007 2008 2009 2010 2011 2012 2013 2014 TTM 3Q-15 M -

100 700 300 500 600 200 400 ($M) ($M)

EALTH management Professional money Access to a unique selection of investment advisers subject to rigorousa dueprocess diligence Portfolios multiple strategies encompassing Flexible, platform open architecture equity investments private Hedge and funds Institutional money ideas investment generating management focused on alpha- Traditional Multi-Asset Strategies Alternative Investments Oppenheimer (OIM) ˗ ˗ ˗ ˗ ˗ ˗ W Advisory Fees as a Percentage of Wealth Advisory . . . 22 2 3Q-15 ($M) 18 (1,2) 7 47% $131.9 (15) Equities Institutional 13 20 24% $65.4 21% Institutional $59.4 Fixed Income 7 Banking Investment LTM 3Q-15 $280M 8% $22.9 (94) Public Finance 27 2007 2008 2009 2010 2011 2012 2013 2014 LTM Capital Markets Revenue Breakdown Capital Markets Operating Profit Capital Markets - 60 20 40 (80) (60) (20) (40) (120) (100) against the firm in ARS matter 280 3Q-15 299 d to arbitration award d levied to arbitration 281 to acquisition to of Capital CIBC U.S. Markets business; ($M) 283 (1) 322 390 ARKETS

M 383 Total Revenue 273 Sales & Trading Equity Research Corporate Access Taxable Fixed Income Non-Taxable Fixed Income 156 2007 2008 2009 2010 2011 2012 2013 2014 LTM Institutional Equities Income Institutional Fixed Investment Banking Public Finance APITAL ˗ ˗ ˗ ˗ ˗ . . . . 2008 was negatively impacted by acquisition costs relating impacted by was negatively 2008 Segment revenue and operating profit as Segment revenue operating reported and 2012 was negatively impacted by a $30M pre-tax charge was relate negatively impacted by a $30M 2012 C - 50 150 100 350 300 250 (1) (2) 200 450 400 23 Services Research Trading Advanced Technology solutions all Full access to available venues class Best in analytics Program Marketing Non-deal road shows Conferences & events Bespoke and customized trips tailored to clients tailored to individual needs    Electronic &   

Strategy Deeply experienced sales, trading and sales, trading specialized research staff Innovative derivative strategies for portfolio hedging Portfolio Securities Proprietary & innovative Investment Strategy, Portfolio Strategy & Technical research   & Convertible Investment & Listed Options  Equity the Markets we serve. Research Arbitrage and Merger Domain expertise in Consumer, Energy, Financial Institutions, Healthcare, Industrials, Technology, Telecom & Internet Full Suite of Event of Full Suite Driven & Merger Arbitrage Strategies Dedicated research staff execution Focus on & liquidity Event Driven     Sales Global Trading QUITIES U.S. Cash Specialized sector traders High-Touch Client service Dedicated Block trading capability Sales teams located Sales teams throughout the US, throughout the London, , Tel & Hong Kong Aviv years of 12 + Average of specialized experience Cross Asset Class capability Institutional E       Premier Research, Trading and Capital Markets Solutions for Premier Research, Trading and Capital Markets

investor access to investor access and growing public private companies Broad capital markets capabilities offering innovative and comprehensive solutions to mid- tier companies NSTITUTIONAL 100+ research professionals covering 570+ companies 100+ sales professionals throughout U.S., U.K., Israel, Asia covering over 3,000 investors Over 1,000 events annually providing I . . . . 24 Finance Trading U.S. Treasuries: Bills; Notes; Bonds TIPS STRIPS REPO Treasury Agency Mortgages Trading and Government High Yield Non-Investment Grade Corporate Issuers         Markets Trading Emerging Investment EMEA, LATAM, Asia Corporates and Sovereigns Grade Credit U.S. Dollar Denominated Investment Grade Corporate Issuers   Trading Euro Bond Non-U.S. Dollar Denominated Foreign Issuers Underwriting and trading of Tax- exempt Taxable Bank Qualified High Yield Municipal Bonds Municipals & Public Finance     

NCOME I Trading Trading Money funds Commercial Paper Certificates of Deposit Short Term

IXED TBAs Pass-throughs CMOs ARMs CMBS ABS Asset Backed Mortgage and    Product Capabilities

F      

NSTITUTIONAL 100 Institutional Sales People and 60 Traders $115B More than raised since 2004 $100B More than bonds traded in 2014 ~1,500 Active Accounts I . . . . 25 $83.9B (1) Energy & 17% Industrials M&A, 368 2012 – 3Q-15 83% Capital Raising, Engagements Investment Banking Period: Deals: # of Transaction Volume: Financial    Reflects all announced deals and disclosed deal deals and announced Reflects all Institutions (1) values; data is sourced from Dealogic, CapIQ deal and records Industry Coverage

ANKING B Full-service investment banking capabilities focused on middle-market and emerging growth clients Multi-sector, multi-product model enlarges market diversifies opportunity and the revenue stream sponsor coverage financial Corporate and industry coverage Directors lead Experienced Managing and product teams to provide best-in-class execution Focus on growing the franchise by recruiting top performers with experience serving Oppenheimer’s target client Technology Healthcare Consumer Business Services NVESTMENT

I . . . . . 26 4,091 33.0% 4,135 4,135 36.6% 3,885 Permanent Loans 3,394 33.4% 2,632 42.8% 1,368 Construction Loans Loans Construction 528 Operating Profit Margin Operating Profit 2011 2012 2013 2014 LTM 3Q-15 Principal Loan Balance ($M) 39.5% 285 2008 2009 2010 2011 2012 2013 2014 3Q-15 5.0% 5.0% 0.0% 15.0% 15.0% 10.0% 35.0% 30.0% 25.0% - 20.0% 45.0% 45.0% 40.0% 40.0% 500 1,500 1,000 3,500 3,000 2,500 2,000 4,500 4,000

ANKING 508 B 505 (1) 470 424 ORTGAGE interest belongs to belongs interest

M 341 212 M as M of September 30, 2015 118 Number of Loans in Servicing 85 2008 2009 2010 2011 2012 2013 2014 3Q-15

OMMERCIAL Escrow deposits of $309.1 Commercial Mortgage Banking segment is made up of Oppenheimer Multifamily Housing & Healthcare Finance, Inc., a Pennsylvania corporation (“OMHHF”) controlling The Firm owns an 83.68% interest; remaining non-controlling President and CEO of OMHHF of FHA-insured multifamily Originator and servicer loans facility and healthcare FHA-insured mortgage lender Top 10 -

C 100 300 500 (1) 600 200 400 . . . . THANK YOU FOR YOUR TIME