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    Oppenheimer Holdings Inc. Annual Report 2015

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    Oppenheimer is a leading investment bank and full-service investment firm that provides financial services and advice to high net worth investors, individuals, businesses and institutions. For over 130 years, we have provided investors with the necessary expertise and insight to meet the challenge of achieving their financial goals. Our commitment to our clients’ investment needs, our experienced and dedicated professionals, and our proud tradition empower us to deliver effective and innovative solutions to our clients. Our Business Principles Client Focus Trusted Reputation We are deeply committed to our clients and offer Our track record demonstrates a commitment to the same level of service to investors of all sizes. results-driven investments and leadership in the financial marketplace. Tailored Advice Flexibility at Scale Our recommendations for each client are tailored Our structure allows teams to scale to meet a and based on a deep-seated knowledge of client’s needs, pulling together the right expertise to individual goals. meet each challenge. Open Architecture Heritage and Continuity We foster a culture of independence and autonomy For more than 130 years we have provided our and offer clients direct access to decision-makers. clients with the financial expertise and insight to meet their goals. Proven Expertise Entrepreneurial Mindset We have earned a role as a trusted advisor for our We believe in independent thinking that leads to clients by consistently providing expertise, insight, innovative financial solutions. and results.

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    FINANCIAL HIGHLIGHTS—Annual Report 2015 (In thousands of dollars except per share amounts and number of employees) 2015 2014 2013 2012 2011 Gross revenue $928,385 $1,004,464 $1,019,714 $952,612 $958,992 Profit (loss) before income taxes $6,711 $25,736 $43,909 ($527) $17,848 Net profit (loss)* $1,962 $8,826 $25,061 ($3,613) $10,316 Basic earnings (loss) per share* $0.14 $0.65 $1.85 ($0.27) $0.76 Total assets $2,692,964 $2,787,455 $2,952,720 $2,678,020 $3,527,439 Shareholders’ equity* $518,058 $527,644 $522,518 $500,740 $508,070 Book value per share* $38.84 $38.71 $38.77 $36.80 $37.16 Total shares outstanding 13,338 13,630 13,478 13,608 13,672 Number of employees 3,290 3,434 3,517 3,521 3,576 GROSS REVENUE NET PROFIT* ($ thousands) ($ thousands) 11 958,992 11 10,316 12 952,612 12 (3,613) 13 1,019,714 13 25,061 14 1,004,464 14 8,826 15 928,385 15 1,962 SHAREHOLDERS’ EQUITY BOOK VALUE PER SHARE ($ thousands) ($) 11 508,070 11 37.16 12 500,740 12 36.80 13 522,518 13 38.77 14 533,732 14 38.71 15 518,058 15 38.84 ASSETS UNDER MANAGEMENT CLIENT ASSETS ($ billions) ($ billions) 11 18.6 11 76.0 12 20.9 12 80.3 13 25.3 13 84.6 14 25.9 14 87.3 15 24.1 15 78.7 FINANCIAL ADVISORS BRANCH OFFICES 11 1,427 11 94 12 1,406 12 86 13 1,388 13 96 14 1,324 14 92 15 1,233 15 85 * Attributable to Oppenheimer Holdings Inc. 1

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    Dear Fellow Shareholders At year-end, we are called upon to review what happened For the year, the Company reported revenues of $928.3 million, a during the year and, more importantly, identify issues and chal- decrease of 7.6% from $1 billion in the prior year, and reported a lenges that shaped the year, as well as how we plan to best profit of $2.0 million, compared to a profit of $8.8 million, a de- address them in the future. crease of 77.8% from 2014. The 2015 profit per share was $0.14 ($0.14 fully diluted) compared to a profit of $0.65 per share ($0.62 In the financial services industry as well as at Oppenheimer, we fully diluted) in 2014. On December 31, 2015, the Company had see ahead of us great opportunities for new growth and new a total of 13,338,000 shares outstanding and the book value per prosperity, even as we successfully resolve issues and challenges share was $38.84 as compared to $38.71 at the end of 2014. of the past. It has never been more important to be looking forward in our planning and priorities to stay ahead of rapidly Our full-year results produced lower revenue, which reflected changing economic conditions, the evolution of financial mar- weakness across several business lines. In our private client busi- kets, regulatory initiatives, and, above all, the unknowns which ness, we observed a sharp decrease in account turnover with lie beyond our influence and control. In this letter, we will dis- commissions at the lowest level (per dollar of assets under cus- cuss our determined approach to all of these developments and tody) we have ever experienced. Also impacted was our institu- our optimism toward the future success of our firm. tional equity business, and although it showed flat revenue, our market share again increased this year. In investment banking, The equity markets in 2015 proved to be disappointing, with we had lower revenue, largely reflecting lower capital markets the benchmark S&P 500 index down less than 1%. A sharp activity from IPOs and secondary offerings. reduction in the price of oil ($38 per barrel at year-end) and a strong U.S. dollar, as measured against a basket of currencies, For the first time in our history, we produced fee-based rev- led to modest growth in the U.S. economy (2.4%). In Decem- enue from asset management that exceeded our transaction ber, the Federal Reserve ended its 8-year commitment to low business, indicating continued growth and client acceptance of interest rates with a widely anticipated increase in the discount fee programs over commission-based transactions. Once again, rate. This, in combination with a further drop in crude oil, re- incentive fees from alternative investments were disappointing sulted in an incredibly weak start to 2016. This appears to be a due to the inability of these investments to reach “high water reaction to an unexpected weakening of the global economy. mark” levels in a difficult and highly volatile equity environment. Reporting on our results for 2015, client assets under adminis- We continue to observe redemptions of client-held auction tration totaled approximately $78.7 billion, while client assets rate securities and client holdings eligible for firm tenders were under management in fee-based programs totaled approxi- down to $57 million at year-end compared to total client hold- mately $24.1 billion, compared to $87.3 billion and $25.9 bil- ings of $2.8 billion when the auction rate market failed in 2008. lion, respectively in 2014, reflecting weaker valuations and a While this situation is not completely resolved (we hold on a smaller salesforce. proprietary basis auction rate securities totaling $92 million), 2

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    the prospect of higher short-term interest rates in 2016 should in the face of significant challenges. The regulatory environment incentivize issuers to redeem that which remains. continues to be a concern with elevated levels of oversight and considerable industry-wide uncertainty surrounding a host of During the past year, we showed progress in a number of im- new regulatory requirements. We are investing in enhancing and portant areas: strengthening our compliance regime, working with indepen- dent consultants and regulators, adding senior and experienced We successfully recruited Financial Advisors across the country. compliance management, and upgrading technology. We are We are focused on the need to recruit and retain experienced emphasizing the critical and immediate need to combat cyberse- Financial Advisors with proven records in order to continue to curity threats and to protect privacy. Be assured that we are firmly build and preserve this important franchise. We will ensure our committed to undertake any and all actions necessary to protect success by investing in existing people through professional our company and, most importantly, our clients. development and succession planning programs. A strategy of growing individuals that hold a deep understanding of our We have made a number of mistakes in recent years. Some of operations, capabilities, and client needs and expectations will them have been quite painful and costly. But we have learned provide both a solid basis for future success, while we continue much from our mistakes. Our core values and our culture are the to enhance and deliver a platform with best-in-class investment most important and enduring strength of this firm. As we stay true ideas and outstanding services. to our principles, always doing what is right and best for our clients in the best and worst of times, we can feel justly proud of our ef- Our success in attracting clients to our various asset management forts. As we make the changes necessary to evolve and to adapt, strategies continued to show substantial progress with such fee- we face the future from a position of strength. based programs for the first time exceeding 50% of private client revenues. While the number of clients increased, overall assets The talented and tireless efforts of our employees are yielding under management decreased, due largely to market value de- solid and steady gains. We have the advantage of a fully en- clines. Prudent asset allocation and cogent manager selection gaged and firmly committed Board, fully engaged in the evolv- are finding wide and enthusiastic receptivity among clients that ing policies and practices of the Company and firmly committed greatly appreciate our holistic view of investments. to overseeing the necessary changes to ensure our future suc- We continue to see growth in market share of our institutional cess. All of this reinforces my conviction that by working togeth- equity platform. Client meetings with company management er, not only will we meet and master any and all past challenges, and heavily attended industry conferences continue to reinforce but we will seize and exploit future opportunities to ensure that the value of bringing actionable ideas and corporate represen- Oppenheimer’s best days are ahead of us. tatives to institutional clients. Our equity research analysts con- More than 30 years with Oppenheimer have instilled in me a tinue to be widely respected for their thoughtful and innovative deep pride for what we do. We create trusted relationships with ideas. We ended the year with 40 publishing analysts across clients and one another. We also believe that we gain a com- multiple industries. petitive advantage from our size and intimate company culture– Among our technology initiatives, we successfully launched a new a culture firmly rooted in our values, which emphasize ethics Mobile App, and by year-end 2016, the launch of Passport, our and integrity, trust and respect. Our size, our culture, and our new asset management technology platform, will bring a substan- teamwork have always given us a competitive advantage. I am tial upgrade to advisor access to client data as well as improved confident that will continue. tools to implement and execute client investment programs. We continue to evaluate and enhance the client online experience with I want to express my thanks and that of our firm to the many improved and expanded access to account information. years of dedicated service on our Board of Ken McArthur and Dick Crystal, both of whom will be retiring as directors at our This year, we invested heavily in regulatory and control solutions upcoming Annual Meeting. We will miss them. by hiring the experienced people necessary to develop and im- prove the technology required by our compliance programs. We I express my appreciation and gratitude to you, our sharehold- believe that such investments are necessary in order to ensure ers, for your continued support. that in everything we do, we are meeting and exceeding the requirements of the regulatory environment. We continue to build for the long term, execute on a comprehen- Albert G. Lowenthal sive strategy for growth and believe in our ongoing success, even Chairman & CEO 3

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    Private Client Division • 1,233 Advisors AT A GLANCE The Private Client Division is comprised of 1,233 Financial Advisors who are • 85 Offices located in 85 offices throughout the United States. Our Financial Advisors • $78.7 Billion provide comprehensive investment solutions to a variety of clients that include Assets under high net­worth individuals and their families, endowments, charities, pension Administration plans, corporate executives and a range of businesses. Our Financial Advisors offer unmatched access to intellectual capital combined with the support of our Financial Planning Group, Trust Company, Asset Management Group, Insurance Division and both Corporate Executive and Retirement Planning services. BUSINESS ENVIRONMENT • The continued development of our employees through 2015 was a year that continued with a slow growth, low interest Professional Development and the acquisition of additional rate environment that saw increased market volatility that adversely talent and expertise to meet the ongoing needs of our clients. affected investor confidence and activity. The markets focused on continued uncertainty surrounding declines in the price of oil and • The continued investments in our compliance and operating other commodities, the perceived weakness in China’s economy, systems to enhance our risk management controls while the strengthening dollar and the timing of the Federal Reserve’s improving our efficiencies and productivity. decision on increasing short­term interest rates. Despite reaching a record high on May 21, the S&P ended the year slightly down. Our business is built on relationships and people are our greatest asset. During 2015, we made significant changes in our leadership During a year of volatile markets and client uncertainty, Oppen­ ranks, our compliance team and processes, and in programs to heimer Advisors continued to work closely with their clients in help our advisors and their teams grow professionally. In addition, developing strategies to take advantage of these changing markets. we invested resources to ensure that our business lives up to the ACCOMPLISHMENTS highest levels of compliance and integrity. In meeting this goal, The Private Client Division has a clear strategy: we realigned our model in accordance with expected industry • To continue to develop comprehensive wealth management practices and added 16 professionals to our already expanded strategies to meet the investment needs of our clients. compliance team. 4

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    Targeting Growth Opportunities consultations and individual coaching. For newer employees, we Our strategy aligns our business with two key demographic trends strengthened our Associate Advisor, internship and mentoring that are developing: Intergenerational wealth transfer which is programs. These programs are designed to help Financial Advisors occurring between Baby Boomers and their beneficiaries and an grow and manage businesses oriented to attracting new clients aging and declining advisor population. and expanded access to client sources of wealth. As Baby Boomers continue to plan for the future, they increasingly are looking for solutions for overall retirement planning and advice With the new OpcoMobile app, on complex issues. Oppenheimer’s platform and financial plan- clients have seamless access to ning approach are particularly well suited to this market and our Financial Advisors are highly successful in guiding these individuals their accounts anytime, anywhere. and families. Oppenheimer Life Agency, Ltd. and Oppenheimer Trust Company of Delaware provide leading trust, annuity and Technology and Infrastructure insurance solutions that are so important to clients. Our employees and our clients also need intuitive technology and we are delivering it. Through a sounding board of client-facing advisors As Millennials continue to exert both their economic force and their and support, we focus our technology enhancements on the most worldview, we are planning for changes in our advisor population as value-added projects. We continue to roll out an integrated platform well as in our product offerings, and an enhanced delivery model, that provides simplicity and scalability for our Financial Advisors more attuned to a technology savvy population. We launched and and multi-channel delivery for our clients. As our world migrates developed an internship program that has grown and become a to mobile platforms, we delivered the OpcoMobile app to provide source of younger talent to our advisor community. Through our clients with access to their accounts on both Apple and Android professional development effort, we provide a pathway for the next devices. Other enhancements in 2015 included a much improved generation where older advisors begin the process of succession enrollment process and the ability for clients to determine their planning with their younger family members. preferences for delivery of information and grouping of accounts. Professional Development THE WAY FORWARD Under new leadership, we re-launched our professional develop- We are committed to providing our clients with superior solutions ment organization to help advisors continue to grow their practices and financial advice best suited to their stage in life and their goals. using a variety of methods such as skill-based training, peer-to-peer With new leadership and structures in place, we will concentrate all exchanges and practice management tools. We conduct ongo- our efforts on unlocking the full potential of our business through ing formal training programs for all Financial Advisors including meeting client needs and expectations, supporting our advisors as providing advisors a methodology to transition their practice to a they build and nurture their businesses and executing on a strategy client focused fee-based model. We also provide business model to grow our business while carefully managing risk. 5

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    Asset Management • $24.1 billion in AT A GLANCE Assets Under Oppenheimer Asset Management (OAM) is committed to its mission to Management provide investment advice and investment management services that best • 61,415 client meet the needs and objectives of our clients. Our guiding principles for accounts advising high net worth individuals, endowments, foundations and other institutional clients focus on understanding our client’s definitions of risk and • 10 programs reward, coupled with recognition that the key benchmark to meet is helping our clients achieve their stated goals through prudent diversification. ACCOMPLISHMENTS As PASSPORT is launched to our advisor network, we will retire 2015 was a year of transitions for OAM. New leadership and 14 operating systems in order to streamline the data collection the implementation of initiatives will transform our business and process and reduce administrative overhead. Additionally, in position the group well for future growth. Key initiatives such as: 2016, OAM will take on the Unified Managed Account (“UMA”) implementation of a state of the art advisor­centric technology; the overlay portfolio management responsibility for over $4.5 billion buildout of additional sales and marketing resources; integration in client assets, creating both more efficiency and improving into actionable investment ideas of the firm’s global investment our operating margins, while providing enhanced reporting to strategy, and continuous support of our key constituencies both our clients. This integrated platform will empower advisors to advisers and clients. We continued to source innovative investment continue to customize their advisory services offering and create strategies within both traditional and alternative asset classes in administrative efficiencies. It will also free up our advisors to focus order to provide a solid foundation from which to build. on client attention and relationships, their most important role. Technology Sales and Marketing The introduction of PASSPORT, OAM’s new wealth management OAM expanded its sales and marketing footprint by 75% in 2015, platform, marks a significant commitment by the firm to improve hiring talented associates to help meet the growing demand of the Financial Advisor and client technology experience. PASSPORT the firm’s U.S. based wealth management effort. With a 10:1 will provide “power at the desktop”, delivering tools to view, trade Financial Advisor to OAM personnel ratio, Financial Advisors and and manage client advisory accounts with both efficiency and scale. clients are afforded the resources one would come to expect 6

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    from a full service advisory platform such as ours, delivered the OAM Market Strategy Portfolio, an efficient means through with a level of personal engagement and support rarely seen in which clients can invest in the trends and themes the Group today’s marketplace. believes are relevant to investment success. These beliefs are expressed through the careful selection of highly liquid ETFs Throughout 2015, the Sales and Marketing group reinforced existing that vary in investment style, market capitalization ranges and advisor relationships and forged new relationships by focusing geographic regions and provide access to high quality underlying on an effort to educate Financial Advisors and their clients on equity investments. The OAM Market Strategy Portfolio launched OAM’s investment and wealth management capabilities. Our in 4th quarter 2015. increased manpower enables us to provide support to a wider geographic distribution of offices as well as high visibility training Manager Sourcing and investment seminars, sponsored client events and direct client Discovering emerging talent remains a focus for OAM. Whether engagement, all of which are critical to our unique approach to traditional or alternative, the firm’s history of identifying specialized client support and education. niches of the capital markets in which to invest in continues to be where the best investment opportunities are to be found. The ability to engage with clients is further strengthened by Identifying those managers with specialized knowledge, strong the integration of the firm’s financial planning resources, key to pedigrees and unique and differentiated investment approaches providing proper context for client investment strategy. Financial that best align with our views on appropriate allocation and Advisors have adopted the financial planning process as a key diversification are the foundation of OAM’s manager platform. component of their ability to assist clients in the proper review OAM has identified forty such discovered/emerging manager of their current financial profile and meeting their financial goals strategies across both traditional and alternative investments. both now and in the future. While 2015 ended with most major market indices experienc- ing losses, the platform produced relatively strong risk-adjusted PASSPORT will provide performance, particularly in alternative investments with most strategies outperforming their primary benchmarks. Our belief ‘power at the desktop’ in preservation of capital and better performance through diver- sification gave ample testimony this past year to our philosophy Thematic Trends of the importance of manager selection. The Market Strategy Group was formally incorporated into OAM in 2015. Working in conjunction with our traditional and alterna- THE WAY FORWARD tive investment research teams, the Group provides actionable, We believe our expanded reach along with the investment products markets-based advice through its weekly “The Market Strategy and services available through OAM will help us to navigate and Radar Screen” publication. OAM’s work inspired the creation of weather whatever the markets may bring in 2016. 7

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    Equity Capital Markets • A research department with more than 100 research professionals AT A GLANCE providing in­depth coverage of over 570 companies across a wide The Equities Group is committed range of industries, with a particular focus on mid­ and small­cap to creating exceptional value for companies our corporate and institutional • Over 100 institutional sales professionals operating throughout clients. Our goal is to be the the U.S., U.K., Israel, Asia and Europe through our various offices premier research, trading and and affiliates capital solutions firm for the • A global trading and execution platform that provides execution markets we choose to serve. in all venues and on numerous exchanges throughout the world • An Equity Capital Markets Group that offers innovative and comprehensive capital markets solutions BUSINESS ENVIRONMENT several high profile IPO names coming to the market, the IPO cal­ Many market participants closed out their books at the end of 2015 endar was a disappointment, driven by concerns around valuations with a sigh of relief. Despite the headline averages ending the year and heavily impacted by market volatility and a considerably more virtually unchanged, it felt like a long, long journey to get there. selective attitude on the part of institutional investors, scarred by the Action was mostly driven by macro events on the global stage, triple­digit dips and sharp rallies that occurred throughout the year. although at home the expected cycle of Fed rate rises became a nerve­wracking game of chicken with the markets. An epic collapse ACCOMPLISHMENTS in the price of oil and other commodities caused a great deal of pain Oppenheimer’s Equity division delivered a solid result for the year, for investors, especially in the energy sector and related industries. with core agency commissions coming in about on par with the In turn those dramatic events generated significant volatility in prior year. Our salesforce was able to hold market share gains from markets generally, with the VIX volatility index spiking from a low 2014, and in a number of cases we saw continued improvement in point of 11 to a high of 40 during the course of the year. market share as our clients came to appreciate the full depth and breadth of our research product. Bolstered by our highly regarded Volatility, as well as continued lower than normal volume, made Investor Conference series, we continue to achieve client recognition for a challenging year for the equities industry as a whole, as both especially in our key verticals: Technology, Telecom & Internet, institutional and retail participants remained side­lined. Despite Healthcare and the Consumer Industry. In 2015, we also experienced 8

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    renewed growth in our Event Driven and Merger Arbitrage business Healthcare Conference, and also created a smaller, more intimate line, as that group capitalized on a surge in M&A activity in the scientific event series, called Oppenheimer’s On-Site Insight Series, U.S. and around the globe. Additionally, we were very pleased which focused specifically on immuno-oncology. to see another significant increase in revenue from clients of our options desk. The jump in volatility combined with the need for The Equity Capital Markets group completed 84 transactions raising investors to hedge their portfolios led to both new and existing $17 billion in 2015. With a primary focus on mid- and small-cap clients engaging with this specialized sales team. growth companies, Oppenheimer’s median deal size was $80 million with a market cap of $425 million. The backdrop for the year was The Equity Research Department ended 2015 with over 600 stocks one in which we had a very healthy capital raising environment under coverage and 40 senior research analysts. There was con- for the first two quarters of the year and then a more challenging tinued interest across our client base in all of the core verticals: environment in the last two quarters. The IPO market saw 159 Technology, Internet & Communications, Consumer, Healthcare, IPOs raising $30 billion and 611 follow-on transactions raising $165 Industrials, and Financial Institutions. At our conferences in 2015, billion according to Dealogic. The dominant sector for the year we hosted close to 450 companies and arranged over five thousand was healthcare, with life sciences comprising the majority of the individual meetings for investors. Access to company managements transactions. Healthcare IPOs accounted for 43% of the market by issuer and 37% of the follow-on market by issuer. Oppenheimer grew its healthcare financings by 35% from 26 transactions in 2014 Oppenheimer grew its healthcare to 40 transactions in 2015. The technology, consumer, financials financings by 35% from 26 and energy sectors were also active for parts of the year and Oppenheimer engaged in a number of financings in those areas transactions in 2014 to 40 as well. We served as bookrunner or lead manager on 23 trans- transactions in 2015. actions throughout the year, including being a joint bookrunner on a successful U.S. listing for Summit Therapeutics plc and a joint remained a strong bulwark of our strategy as we took over 400 bookrunner on the successful uplisting of Pieris Pharmaceuticals. companies on the road and hosted over 3,000 individual meetings. In addition, we had multiple other book-run and lead assignments In the second half of the year, we entered a new sector, Sustain- in the technology, financial and industrial space. able Growth & Resource Optimization, which should be a large and growing industry over the next few years. On the technology THE WAY FORWARD side, our analysts continue to focus on the convergence that is Oppenheimer’s Equity business is well positioned for 2016. We rapidly occurring between technology and communication, and are digging deeper and working harder and smarter. We have we hosted several cross-sector events for investors to help provide focused resources on areas where our domain strengths and our insight into the changing technology landscape. Our Healthcare clients’ need coincide. By consistently delivering the highest level franchise experienced a solid year, capitalizing on investor interest of service in each segment, market share will continue to grow in the war on cancer. We concluded the year with our 26th Annual in the coming fiscal year. 9

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    Investment Oppenheimer’s investment banking business substantially in 2014, underscoring positive market trends grew Banking and the progress the division has made under new leadership since 2012. Investment Banking management’s strategy continues to center on three core business initiatives to better position our business within the current market environment: (i) expanding the breadth and depth of solutions for our clients; (ii) refining our ability to execute on behalf of our clients; and (iii) attracting and retaining talented professionals with deep industry sector domain expertise, transaction experience and relationships in the middle market. • 100 Professionals AT A GLANCE Oppenheimer’s Investment Banking professionals are committed to providing • Completed over 100 transactions strategic advisory services and capital market strategies for emerging growth representing and mid­sized businesses. With our deep industry expertise and broad approximately product capabilities, we are uniquely positioned to assist companies achieve $20 billion in value their strategic and financial goals through a variety of market conditions. BUSINESS ENVIRONMENT These factors contributed to a difficult 2015 for U.S. equity and Geopolitical risks and uncertainty related to monetary policy equity­linked markets. Equity volume was down 11% year over caused pockets of volatility throughout the year. While year, with volatility in the healthcare market and the lowest U.S. economic numbers were positive in aggregate, weak level of technology IPO volume since 2009. The equity­linked data out of China raised concerns over global growth. market saw convertible issuance down 20% from the prior Corporate earnings also came under pressure due to year. The U.S. M&A market was a silver lining. A five­year pricing compression in the oil industry, a continued strong run of increased volume continued with 2015 finishing as the dollar and increased borrowing costs for many, as credit biggest year on record for U.S. targeted M&A, driven largely spreads increased. by transactions in the healthcare and technology sectors. Select M&A Transactions $800,880,000 Undisclosed Undisclosed Undisclosed $92,000,000 Undisclosed a portfolio company of a portfolio company of Wood MobileOffice Fleet Sale to Sale to Sale to Sale to Sale to Sale to UPHILL INVESTMENT Exclusive Financial Advisor Exclusive Financial Advisor Exclusive Financial Advisor Exclusive Financial Advisor Exclusive Financial Advisor Exclusive Financial Advisor December 2015 December 2015 November 2015 July 2015 May 2015 March 2015 10

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    ACCOMPLISHMENTS Finance Group advises public companies regarding capitalization Oppenheimer Investment Banking results mirrored broad trends. strategies and raising capital in situations where regular­way, Our Healthcare and Technology groups led division activity, broadly marketed offerings are often not the optimal solution— in together contributing a majority of our revenues. M&A continued particular, quickly accessing capital for small, less liquid public to be our strongest product and helped to offset the effects companies. The Industrial Technology Group provides strategic of a slowed public financing environment. During the year, we advisory services to clients in the alternative energy, renewables served as financial advisor on announced and completed M&A and clean technology sectors as well as to companies with applied transactions totaling more than $2.0 billion in value. Despite technologies to the industrials sector. market instability, we were able to raise approximately $17.0 billion of equity and equity­linked capital for clients via 84 Investment Banking also developed its franchise in Europe, Middle offerings. A continued appetite for life science equities dedicated East and Africa (EMEA) and Asia and Pacific (APAC) to better to promising drug discoveries and increased public interest in complement U.S. equity and debt capital markets capabilities. the technology space contributed significantly to equity activity. In EMEA, the bank has Consumer, Healthcare, Technology and Communications investment banking capabilities. In APAC, a cov­ While 2015 presented challenges for our industry, management’s erage group focused on financial sponsors and sovereign funds is strategy continued to center on three core business initiatives to designed to assist European and U.S. clients in accessing capital better position our firm as a multi­product, multi­sector platform within the region. within the evolving market environment: • expanding the breadth and depth of solutions for our clients; We improved recruiting and retention. Over 25 professionals joined • refining our ability to execute on behalf of our clients; and, the team, including five senior hires, to maintain a current total • attracting and retaining talented professionals with deep headcount of approximately 100 individuals. We also launched industry sector domain expertise, transaction experience and a program to retain and develop our current Executive Directors relationships in the emerging growth and middle markets as they assume greater accountability for client coverage and revenue generation. The division added product specialist and industry cover­ age bankers including the creation of the Alternative Cap­ THE WAY FORWARD ital Finance Group and Industrial Technology Group. These Despite a volatile 2015, focus on these core business initiatives additions allow Oppenheimer to be an increasingly relevant contributed to the success of the Investment Banking Division. provider of financing solutions to micro and small capitalization We look forward to continuing to bring our clients best­in­class companies across a number of sectors. The Alternative Capital service and effective solutions as we move forward into a new year. Select Financings $150,000,000 $400,000,000 $126,800,000 $51,000,000 $22,500,000 $35,000,000 Placed with Senior Unsecured Notes Initial Public Offering Equity Follow­on Offering Equity Follow­on Offering Private Placement Private Placement Offering Co­Manager Co­Manager Co­Manager Lead Bookrunner Placement Agent Sole Placement Agent December 2015 November 2015 October 2015 September 2015 September 2015 June 2015 $343,735,000 $136,562,500 $3,687,190,000 $228,250,000 $68,770,000 $39,280,000 Equity Follow­on Offering Initial Public Offering Equity Follow­on Offering Equity Follow­on Offering Equity Follow­on Offering Equity Follow­on Offering Co­Manager Lead Manager Co­Manager Co­Manager Co­Lead Manager Bookrunner June 2015 May 2015 March 2015 March 2015 March 2015 March 2015 11

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    Debt Capital Markets • A global trading and execution platform AT A GLANCE • Over 100 institutional sales and over 60 trading professionals The Fixed Income Group is operating throughout the U.S., U.K., Israel, Asia and Europe committed to creating exceptional value for our corporate, municipal • Serving over 1,500 institutional accounts in over 60 countries and institutional clients. Our • A research department with 7 research professionals covering goal is to be a premier research, more than 250 companies across a wide range of industries, with trading and capital solutions firm a particular focus on high­yield and emerging markets corporates for the markets we serve. and sovereigns BUSINESS ENVIRONMENT The debate between passive and active portfolio management The fixed income market in 2015 saw a continuation of themes remained a timely subject, particularly for investment products that negatively impacted the credit markets in 2014. The Federal that faced liquidity constraints in distressed markets. In 2015, Reserve continued to create market uncertainty throughout the we saw both ETFs and actively managed bond funds faced with year by delaying a rise in the benchmark Fed Funds rate until the varying degrees of structural challenges. A single market event, final weeks of December. Growth in China continued to disap­ the gating by The Third Avenue Credit Fund startled investors, point investor expectations. The U.S. dollar appreciated against significantly affecting once easily traded fixed income ETFs which all major currencies. Oil prices continued to decline to levels not saw their prices slide further than the underlying bonds they seen in over a decade. Volatility in the stock market, particularly in own, causing them to trade at a significant discount to fair value. August, continued to destabilize investor confidence. Credit spreads continued to widen for High Yield and Emerging Market bonds. ACCOMPLISHMENTS Oppenheimer continued to invest in a strategy of providing timely These trends accompanied tremendous volatility, whereby investors witnessed dramatic swings in benchmark treasury rates and major ideas and advice to our clients, while remaining conservative with stock market averages. However, there was little year­over­year our deployment of capital. Our fixed income research analysts change in treasury yields and stock market indexes were also cover high yield corporate credit, emerging market corporate largely unchanged for the full year. The 10­year treasury yield and sovereign credit, as well as tax­exempt municipal bonds and started the year at 2.11% and ended at 2.27% mortgage backed securities. 12

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    Our Debt Capital Markets group expanded to include origination from the previous year. Both the 10-year and 30-year municipal personnel in New York and London. This complements our global yields ended 2015 with ratios below 90% of treasury yields after sales and trading team, with over 1,500 accounts in 60 countries. starting the year over 100%. Oppenheimer is uniquely positioned to lead-manage deals for both sovereign and corporate issuers looking to raise debt capital from Total municipal bond issuance rose to $435 billion in 2015. How- institutions around the world. Our syndicate desk participated ever, net issuance ended the year at about negative $15 billion. in 16 deals in a variety of industries, including financial, telecom, While there was some headline risk in municipals throughout logistics and travel and leisure. This is up from 14 deals in 2014. 2015, investors continued to flock to the market. Municipal bond funds saw $16.3 billion of positive inflows in 2015. Our Fixed Income division performed well in 2015. Revenues were up slightly from 2014, and despite dramatic price moves in Oppenheimer senior-managed 200 deals totaling approximately High Yield and Emerging Bond Markets, we were able to remain $1.7 billion. Most notably, we increased our position in the number extremely active with clients, while not increasing our risk profile. of school districts we priced in Texas under the Permanent School Our capabilities continue to differentiate us in an environment Fund Program. In addition, we senior-managed multiple issues where bulge bracket players are reducing staff and removing of charter schools located in various states, including California, capital committed to the fixed income business. Oppenheimer’s Massachusetts and Texas. In the competitive new issue arena, Fixed Income business is an increasingly attractive business model Oppenheimer participated in 654 issues totaling over $17 billion, that presents career opportunities for our talented associates providing new issue municipal bonds for our investors. and provides us with a unique ability to add experienced people. THE WAY FORWARD 2016 promises to be another exciting year in the markets. Investors We continue to invest in the are hoping for a bottom to the decline in oil prices and see a modest buildout of our Fixed Income recovery in the energy sector. However, the market seems likely to put further pressure on over-levered issuers with insufficient business and anticipate future cash flow to support their debt obligations. In addition, record opportunity in a market with low commodity prices and the continued strength of the U.S. dollar will threaten once high-flying emerging economies faced fewer full service providers. with potential capital flight. Municipal Bond Sales & Trading We will continue to recruit experienced and knowledgeable staff as The municipal market was highlighted by a strong second half large scale layoffs and capital retrenchment hinder larger players. resulting in a 3.55% overall return in 2015. Lower supply and We will target opportunities for product expansion and growth in high demand for municipal bonds helped fuel the drop in yields the number of Institutional client relationships covered by the firm. 13

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    Public Finance • Senior manager of $1.7 billion of bonds AT A GLANCE Oppenheimer’s Public Finance Group and notes and Municipal • Municipal notes – provides underwriting and advisory services to a wide variety of borrowers Trading among top ten underwriters by volume in the municipal bond market, including government issuers and private Significant Financings by the companies that serve a public benefit. Municipal Capital Markets Group in 2015 BUSINESS ENVIRONMENT $785,795,000† Low and relatively stable interest rates marked 2015, which saw new issue volume surge New York City Transitional Finance Authority Future Tax Secured Subordinate Bonds in the first quarter before gradually retreating over the remainder of the year. All told, total long­term volume for 2015 was $397.7 billion, a 17% increase from 2014. Much $548,185,000†† California State Public Works Board of this increase can be attributed to bond re­fundings, which increased 28% from 2014. Lease Revenue Refunding Bonds (Various Projects) ACCOMPLISHMENTS In 2015, Oppenheimer remained very active in both the competitive and negotiated $275,055,000** Metropolitan Transportation Authority markets and continued its mission to profitably expand its reach and remain innovative Transportation Revenue Bonds in a market bereft of innovative financings. $97,985,000 * Waco (Texas) Independent School District Oppenheimer’s negotiatedunderwriting increased substantially in 2015, with the firmbook­run­ Unlimited Tax Refunding Bonds ning approximately $1.1 billion of bonds and notes in over 60 transactions. In doing so, $86,315,000 * Oppenheimer’s long­term negotiated rankings jumped from 41st to 29th in the league tables. New Caney (Texas) Independent Much of this increase can be attributed to our banking team in Dallas, which senior­managed School District over $500 million of bonds on behalf of school districts in Texas, up from $89 million in 2014. Unlimited Tax School Building Bonds Notable in this sector were a $98 million deal for Waco Independent School District, three $75,501,000* deals underwritten for New Caney Independent School District totaling $148 million, and five Hudson County (New Jersey) Improvement Authority deals underwritten for Mesquite Independent School District totaling $175 million. County­Guaranteed Pooled Notes (Local Unit Loan Program) Our banking team in the Northeast continues to grow its presence among some of the $43,140,000 * country’s largest issuers and has added professionals to develop and further our relationships. City of Springfield, Missouri Additionally, in 2015, Oppenheimer closed its first sole­managed negotiated deal in Rhode Special Obligation Bonds (Sewer System Improvement Projects) Island and was added as a senior manager for one of that state’s most frequent issuers. $37,005,000* 2015 also saw the introduction of a new product in the municipal market. Our Northeast St. Clair County, Illinois public finance team has collaborated with Oppenheimer Multifamily Housing & Healthcare Taxable General Obligation Refunding Bonds Finance and one of Oppenheimer’s lending partners to provide bridge financing for property $35,775,000* developers that will be receiving loans from FHA sponsored government programs. Two Massachusetts Development Finance Authority such deals were consummated in 2015, and several more are expected in the year ahead. Revenue Bonds (Western New England University) One sector of the market in which Oppenheimer was particularly active in 2015 involves charter schools. While these transactions may be relatively small in issuance size, they require $35,388,228 * City of Ithaca, New York experienced practitioners with expert advice on structure and timing. Oppenheimer was Bond Anticipation Notes successful in providing senior­managed bond offerings on behalf of six charter schools in $25,540,000 * Texas and California, as well as one of the largest charter schools issued in Massachusetts. California Statewide Communities Development Authority Oppenheimer’s short­term underwriting desk continues to be a leader in the industry, Educational Facilities Revenue Bonds (Independence Support, LLC Project) reclaiming its position in the top 10 by volume and ranking fourth in number of issues. Our desk bids daily on transactions in the competitive market and frequently commits * Book Runner capital to underwrite entire issues while simultaneously seeking investors for the issues. ** Co­Senior Manager † Senior Co­Manager †† Co­Manager 14

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    As filed with the U.S. Securities and Exchange Commission on March 4, 2016 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 FORM 10-K (Mark One) ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Our Annual Report on Form 10-K for the year ended December 31, 2015 also serves as our For 2015 Annual the Report fiscal year to Stockholders. ended It is available to December 31, 2015 view and print online on our websiteOR at www.opco.com on the Investor Relations page. A stockholder who wants to receive a paper or email copy TRANSITION REPORT of our PURSUANT Annual Report on Form TO 10-KSECTION for the year13 OR December ended 15(d) OF31, THE SECURITIES EXCHANGE ACT OF 1934 2015 must request one. The report is available, without charge, except for exhibits to theFor the transition report, periodtofrom by (i) writing to Oppenheimer Holdings Inc., 85 Broad Street, 22nd Floor,Commission New York, file New York 10004, number Attention: Secretary, 1-12043 (ii) calling 1-800-221-5588, or (iii) emailing us with your request at info@ opco.com. Exhibits will be provided upon request and payment of a OPPENHEIMER HOLDINGS INC. reasonable fee. (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 of principal executive offices) (Zip Code) Registrant’s Telephone number, including area code: (212) 668-8000 Securities registered pursuant to Section 12(b) of the Act: Title of each class Name of each exchange on which registered Class A non-voting common stock New York Stock Exchange Securities registered pursuant to Section 12(g) of the Act: 15

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    Branch Offices (U.S.) Arizona 304 E. Pine Street 130 Mayer Road 3 Harding Road 16427 North Scottsdale Road Lakeland, FL 33813 Frankenmuth, MI 48734 Red Bank, NJ 07701 Scottsdale, AZ 85254 (863) 686-5393 (989) 652-3251 (732) 224-9000 (480) 596-1211 2601 South Bayshore Drive 9475 Holly Road Park 80 West, Plaza 1 1820 East River Road Miami, FL 33133 Grand Blanc, MI 48439 Saddle Brook, NJ 07663 Tucson, AZ 85718 (305) 860-2600 (810) 694-2980 (201) 845-2300 (520) 396-3098 2000 PGA Boulevard 250 Pearl Street NW 382 Springfield Avenue California Palm Beach Gardens, FL 33408 Grand Rapids, MI 49503 Summit, NJ 07901 10880 Wilshire Boulevard (616) 732-3380 (908) 273-2100 (561) 383-3900 Los Angeles, CA 90024 63 Kercheval Avenue New York (310) 446-7100 783 South Orange Avenue Grosse Pointe Farms, MI 48236 300 Westage Business Center Sarasota, FL 34236 620 Newport Center Drive (313) 886-1200 Fishkill, NY 12524 (941) 363-2800 Newport Beach, CA 92660 (845) 897-8100 555 W. Crosstown Parkway (949) 219-1000 4221 W. Boy Scout Boulevard Kalamazoo, MI 49008 888 Veterans Memorial Highway Tampa, FL 33607 (269) 381-4800 4370 La Jolla Village Drive Hauppauge, NY 11788 (813) 357-2800 San Diego, CA 92122 (631) 382-2500 1007 W. Ann Arbor Trail (858) 202-3800 Georgia Plymouth, MI 48170 100 Jericho Quadrangle 3414 Peachtree Road, NE (734) 454-3751 580 California Street Jericho, NY 11753 Atlanta, GA 30326 (516) 733-1300 San Francisco, CA 94104 (404) 262-5300 810 Michigan Street (415) 438-3000 Port Huron, MI 48060 401 Broadhollow Road Illinois (810) 987-1500 Melville, NY 11747 Colorado 227 East Center Drive 3200 Cherry Creek South Drive (516) 391-4800 Alton, IL 62002 12900 Hall Road Denver, CO 80209 (618) 462-1968 Sterling Heights, MI 48313 125 Broad Street (303) 698-5300 (586) 726-5000 New York, NY 10004 500 West Madison Street (212) 859-9200 Connecticut 3106 Biddle Avenue Chicago, IL 60661 1781 Highland Avenue Wyandotte, MI 48192 (312) 360-5500 200 Park Avenue Cheshire, CT 06410 (734) 284-9630 New York, NY 10166 (203) 272-9400 Kansas (212) 907-4000 Minnesota 811 E. 30th Avenue 100 Mill Plain Road 50 South Sixth Street Hutchinson, KS 67502 825 3rd Avenue Danbury, CT 06811 Minneapolis, MN 55402 (620) 663-5461 New York, NY 10022 (203) 748-2626 (612) 337-2700 (212) 753-9110 10601 Mission Road Missouri 29 West Street 11A Sunset Avenue Leawood, KS 66206 16401 Swingley Ridge Road Litchfield, CT 06759 Westhampton Beach, NY 11978 (913) 383-5100 Chesterfield, MO 63017 (860) 567-8301 (631) 288-7122 (636) 733-1000 534 S. Kansas Avenue 466 Heritage Road 360 Hamilton Avenue Southbury, CT 06488 Topeka, KS 66603 1109-E Southwest Boulevard (785) 235-9281 Jefferson City, MO 65109 White Plains, NY 10607 (203) 264-6511 (914) 328-5010 (573) 636-3141 750 Washington Boulevard 1223 N. Rock Road Wichita, KS 67206 4717 Grand Avenue North Carolina Stamford, CT 06901 10 Brook Street (316) 265-9511 Kansas City, MO 64112 (203) 328-1160 Asheville, NC 28803 (816) 932-7000 Massachusetts (828) 251-7884 District of Columbia 1 Federal Street 4039 S. Fremont Street 5301 Wisconsin Avenue NW 800 Green Valley Road Boston, MA 02110 Springfield, MO 65804 Washington, DC 20015 Greensboro, NC 27408 (617) 428-5500 (417) 886-8005 (202) 296-3030 (336) 574-7500 386 High Street One North Brentwood Boulevard Florida St. Louis, MO 63105 380 Knollwood Street 4855 Technology Way Fall River, MA 02720 Winston-Salem, NC 27103 (314) 746-2500 Boca Raton, FL 33431 (508) 324-4450 (336) 631-3295 (561) 416-8600 New Hampshire Michigan Ohio 30 Penhallow Street 110 East Atlantic Avenue 320 North Main Street 25550 Chagrin Boulevard Portsmouth, NH 03801 Delray Beach, FL 33444 Ann Arbor, MI 48104 (603) 436-7626 Beachwood, Ohio 44122 (561) 894-7200 (734) 747-8040 (216) 765-5900 New Jersey 100 NE 3rd Avenue 325 N. Old Woodward Avenue 18 Columbia Turnpike 5905 E. Galbraith Road Fort Lauderdale, FL 33301 Birmingham, MI 48009 Florham Park, NJ 07932 Cincinnati, OH 45236 (954) 356-8200 (248) 593-3700 (973) 245-4600 (513) 723-9200 6700 Daniels Parkway 6102 Abbott Road 302 Carnegie Center 4449 Easton Way Fort Myers, FL 33912 East Lansing, MI 48823 Princeton, NJ 08540 Columbus, OH 43219 (239) 561-2330 (517) 332-8000 (609) 734-0400 (614) 934-1192 16

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    Pennsylvania 205 Town Center Drive Principal Offices Officers 1525 Valley Center Parkway Virginia Beach, VA 23462 Oppenheimer Holdings Inc. A.G. Lowenthal Bethlehem, PA 18017 (757) 493-5360 85 Broad Street Chairman of the Board and (610) 867-8631 New York, NY 10004 Chief Executive Officer Washington (212) 668-8000 136 W. Main Street 500 108th Avenue NE FAX (212) 943-8728 J.J. Alfano Bloomsburg, PA 17815 info@opco.com Executive Vice President and Bellevue, WA 98004 (570) 784-4210 Chief Financial Officer (425) 709-0400 Oppenheimer & Co. Inc. Corporate Headquarters D.P. McNamara, Esq. 14 East Court Street 701 Pike Street 85 Broad Street Executive Vice President and Doylestown, PA 18901 Seattle, WA 98101 New York, NY 10004 Secretary (215) 348-8104 (206) 757-3400 (212) 668-8000 FAX (212) 943-8728 Board of Directors 500 Old York Road West Virginia R. Crystal Jenkintown, PA 19046 339 West Main Street Capital Markets W. Ehrhardt*° (215) 887-7660 Clarksburg, WV 26301 85 Broad Street P. Friedman° (304) 623-4117 New York, NY 10004 M. Keehner*° 2790 Mosside Boulevard (212) 668-8000 K.W. McArthur* Monroeville, PA 15146 Capital Markets A.W. Oughtred° (412) 858-7300 155 Federal Street E.K. Roberts Offices Boston, MA 02110 A.G. Lowenthal 1818 Market Street (International) (617) 556-3717 R.S. Lowenthal Philadelphia, PA 19103 www.opco.com (215) 656-2800 Hong Kong, China * members of the audit commit- Oppenheimer Investments Oppenheimer Asset tee 101 South Centre Street Management Inc. ° members of the compensation Asia Limited Pottsville, PA 17901 85 Broad Street committee Unit 1002, 10/F Henley Bldg New York, NY 10004  members of the nominating/ (570) 622-4844 5 Queen’s Road, Central, (212) 668-8000 corporate governance commit- Hong Kong FAX (212) 907-4080 tee 2200 Georgetown Drive +852-3658-7301 www.opco.com  members of the special com- Sewickley, PA 15143 mittee (724) 933-4810 London, England Oppenheimer Trust  members of the compliance Oppenheimer Europe, Ltd. Company of Delaware committee Rhode Island 405 Silverside Road, 2nd Floor 6 Gracechurch Street 1 Financial Plaza Wilmington, DE 19809 Independent Registered London EC3V 0AT Providence, RI 02903 (302) 792-3500 Public Accounting Firm United Kingdom (401) 331-1932 FAX (302) 792-3509 44-207-220-1900 Deloitte & Touche LLP Texas OPY Credit Corp. Geneva, Switzerland Branch Registrar and Transfer Agent 901 S. Mopac Expressway 85 Broad Street Computershare Shareholder Oppenheimer Europe, Ltd. New York, NY 10004 Austin, TX 78746 Services LLC 3 Rue du Mont-Blanc (212) 885-4489 (512) 314-2600 480 Washington Boulevard 1201 Geneva FAX (212) 885-4933 AIMS 074-29-135 13455 Noel Road Switzerland Jersey City, NJ 07310 Dallas, TX 75240 Phone: 41-22-906-9090 Freedom Investments, Inc. (972) 450-3800 375 Raritan Center Parkway The Company’s financial information Jersey, Channel Islands Branch Edison, NJ 08837 and press releases are available on 201 Main Street Oppenheimer Europe Ltd. (732) 934-3000 its website, www.opco.com, under 43 Hilgrove Street FAX (732) 934-3095 “Investor Relations”. Fort Worth, TX 76102 (817) 333-3900 St Helier JE2 4SL Oppenheimer Multifamily A copy of the Company’s Annual United Kingdom Housing & Healthcare Finance Report on Form 10-K is available by 711 Louisiana Street 44-153-460-3107 1180 Welsh Road, Suite 210 Houston, TX 77002 request from info@opco.com North Wales, PA 19454 (713) 650-2000 Tel Aviv, Israel (215) 631-9151 Oppenheimer Israel (OPCO) Ltd. FAX (215) 412-4583 322 W. Main Street Top Tower, 50 Dizengoff Street Kenedy, TX 78119 POB 23722 (830) 583-0411 Tel Aviv 61236 Israel 4 Waterway Square Place 972-3-526-2666 The Woodlands, TX 77380 (281) 363-7500 Virginia 200 South 10th Street Richmond, VA 23219 (804) 663-1414 100 Boone Boulevard Vienna, VA 21182 (703) 506-7400 Oppenheimer Holdings Inc. | 17

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

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