Building on a Tradition of 130 Years

Oppenheimer Holdings Inc. | Annual Report 2012

Center point of Downtown Manhattan

Aftermath of Hurricane Sandy at 85 Broad Street

Hurricane Sandy causes evacuation of our new headquarters for 37 days

Oppenheimer, through its principal

subsidiaries, Oppenheimer & Co.

Inc. (a U.S. broker-dealer) and

Oppenheimer Asset Management

Inc., offers a wide range of

investment banking, securities,

investment management and

wealth management services from

94 offices in 26 states and through

local broker-dealers in five foreign

jurisdictions. OPY Credit Corp.

offers syndication as well as trading

of issued corporate loans.

Oppenheimer employs over 3,500

people. Oppenheimer offers trust

and estate services through

Oppenheimer Trust Company.

Oppenheimer Multifamily Housing

& Healthcare Finance, Inc. is

engaged in mortgage brokerage

and servicing. In addition, through

its subsidiary, Freedom Investments,

Inc. and the BUYandHOLD division

of Freedom, Oppenheimer offers

online discount brokerage and

dollar-based investing services.

Despite having 800

employees displaced by

Hurricane Sandy,

Oppenheimer continued to

service its clients.

1

** In past years we have actually disclosed registered personnel, not financial advisors in the chart

Client Assets($ billions)

Financial Advisors**Assets UnderManagement($ billions)

Branch Offices

FINANCIAL HIGHLIGHTS—Annual Report 2012

(In thousands of dollars except per share amounts)

2012 2011 2010 2009 2008

Gross Revenue $952,612 $958,992 $1,036,273 $990,480 $919,823

Profit (loss) before income taxes ($527) $17,848 $67,991 $37,067 ($36,565)

Net profit (loss)* ($3,613) $10,316 $38,532 $20,824 ($19,980)

Basic earnings (loss) per share* ($0.27) $0.76 $2.89 $1.59 ($1.51)

Total assets $2,678,020 $3,527,439 $2,515,062 $2,162,582 $1,506,073

Shareholders’ equity* $500,740 $508,070 $504,330 $461,012 $433,954

Book value per share* $36.80 $37.16 $37.73 $34.88 $33.38

Total shares outstanding 13,608 13,672 13,368 13,218 12,999

Number of employees 3,521 3,576 3576 3,616 3,399

Net Profit*($ thousands)

Shareholders’ Equity($ thousands)

Gross Revenue($ thousands)

* Attributable to Oppenheimer Holdings Inc.

Book Value Per Share($)

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2

Markets performed quite well in 2012,

but participation rates were low, as inves-

tors were consumed with the European

sovereign debt crisis, the U.S. fiscal cliff

and a virulent domestic national elec-

tion. While the economy moved with fits

and starts, broad based market averages

closed the year 14% higher than where

they began. As I am writing this letter,

averages have begun to hit new highs,

exceeding the level reached in 2007. It

is a welcome sign and one from which

Oppenheimer is positioned to benefit.

Client assets under administration

totaled approximately $80.3 billion, a

new milestone, while client assets under

management in fee-based programs

totaled approximately $20.9 billion at

December 31, 2012, also at record levels,

compared to $76 billion and $18.6 billion,

respectively, at December 31, 2011.

During 2012, the Company reported rev-

enues of $953 million, a decrease of .6%

from $959 million in the prior year. We

reported a loss of $3.6 million, compared

to a profit of $10.3 million earned in 2011.

The loss per share was $0.27 ($0.27 fully

diluted) compared to a profit of $.76 per

share ($.74 fully diluted) in the prior year.

At December 31, 2012, the Company had

a total of 13,607,998 shares outstanding

and the book value per share was $36.80

compared to $37.16 at the end of 2011.

Our results were negatively impacted

by expenses associated with significant

litigation costs, the build out of our new

headquarters and low interest rates. On

the positive side, results from our fixed

income businesses, Oppenheimer Mul-

tifamily Housing & Healthcare Finance

and somewhat higher incentive fees from

managed client assets made a meaningful

contribution during the year.

Dealing with the litigation resulting from

the financial crisis proved to be an extraor-

dinarily expensive undertaking again this

past year. We continue to see redemptions

of client-held Auction Rate Securities and

the holdings by clients eligible for firm

tenders were down to $213 million at year-

end as opposed to total client holdings of

$2.8 billion when the auction rate market

failed in 2008. On January 31, 2013, we

received the decision of an arbitration

panel on the U.S. Airways litigation first

filed in 2009. The adverse result with the

panel ordering us to pay $30 million (com-

pared to a claim of approximately $140

million) was a bitter disappointment and

in our view clearly contrary to prevailing

case law. This amount, which was booked

to 2012 results, caused us to show a loss

for the year.

While our results in 2012 were lower

than we would expect in a more normal

environment, we are making progress

in rebuilding profitability in our core

business. With the economy improving,

we believe this trend should continue in

2013. This year will bring its own mix of

successes and challenges, but our direc-

tion is clear. We will be diligent with what

we can control: providing our clients with

the best service and most comprehensive

financial solutions in the marketplace and

doing our best to deliver the high quality

advice and guidance that our clients have

a right to expect. We take very seriously

the responsibilities we have to help our

clients succeed.

Our move to our new headquarters pro-

ceeded quite well and uneventfully up

until the onslaught of Hurricane Sandy in

late October. Both our old headquarters

and our new one saw their basements

DEAR FELLOW SHAREHOLDERS

The year just ended was consumed with dealing with crisis-induced issues arising in years past.

Litigation stemming from the 2008-2009 period dogged us throughout the year. This, combined with

continued low interest rates and equity capital markets that continued to be impaired by a slow

growing economy, dramatically affected our results. These issues may, however, finally be moving to

the rearview mirror. We expect less litigation expense and modestly higher interest rates as we move

into 2013 and are seeing equity markets jumping off to a very strong start in this New Year.

3

filled with millions of gallons of salt water,

ruining building infrastructure and making

both of them un-inhabitable for over 30

days. The combined effects of dislocating

over 800 of our employees, the issues

faced by many of them with homes with

no power, as well as a city whose electric

power and transportation systems were

crippled, were quite daunting. While we

will never know the revenue lost from so

many of our people working from tempo-

rary locations and from home, we are quite

proud of our ability to continue to provide

essential uninterrupted service to all of

our clients and our employees at offices

in unaffected regions of the country. We

are deeply grateful to the tireless efforts of

so many of our infrastructure employees

who spent sustained periods of time away

from their homes and families, during a

time when they were sorely needed there.

All in all, it was quite an experience.

Final construction of the new floors of

our headquarters has resumed, and we

expect to reach full occupancy by late

spring. Accounting for the move had a

decidedly negative effect on our earnings

in 2012, despite the long-term savings

that will be realized over the life of our

occupancy; however, we will begin to

enjoy the benefit of those savings in 2013.

During the past year we showed progress

in a number of areas:

• We hired 66 experienced financial

advisors across the country, adding to

recently opened offices as well as long

established ones.

• We increased our ability to transact in

emerging market debt around the world

by adding traders and experienced sales

talent as well as opening relationships with

institutional clients throughout Europe,

Asia and the U.S. We saw increased reve-

nues as a result and great opportunities as

the economies of these nations accelerate.

• We finished the year with 34 senior

publishing equity analysts covering ap-

proximately 600 public companies.

• We added new funds to our alterna-

tives platform and saw significant ac-

ceptance among sophisticated investors.

Increasingly, investors want and expect to

see differentiated opportunities from their

advisors, and we believe we remain in the

forefront in offering such investments.

Risk management is an integral part of

our business operations. Our goal is to

set a tone and create a risk manage-

ment culture in which every employee is

empowered to raise an issue or express

a concern. That means having a well-de-

fined, clear-cut business model, a strate-

gy that puts that model into practice and

operating principles to guide the thou-

sands of daily decisions that are made

by managers across the company. Given

our recent experience with Hurricane

Sandy, we are putting specific emphasis

on improving operational risk awareness

and execution throughout the company.

The investments we continue to make in

our people and the build out of our busi-

ness lines are yielding results. I am grateful

to the men and women of Oppenheimer

for their continued commitment to serv-

ing clients. The relationships arising from

this dedication have never been more

important or more productive as our

many professionals assist in navigating

a volatile environment.

We will pay particular attention to areas of

our business that appear most promising

– including a goal of reaching $1.25 billion

in revenues by 2018. This requires con-

tinuing to add productive financial advi-

sors, attracting experienced investment

banking talent and adding market and

trading expertise in the emerging markets

that we expect will outgrow traditional

developed markets in the years ahead.

The problems afflicting the world econ-

omy today are real and troubling. They

may even cause the opportunities we

foresee for this business to take shape

with less vigor than we would hope.

However, we think those opportunities

will surely materialize – the vast accumu-

lation of wealth will support demand for

investment services well into the future.

Oppenheimer’s future rests on a foun-

dation of enduring principles. Our core

values – integrity, quality, commitment

– have sustained the loyalty of genera-

tions of clients and continue to motivate

talented employees. These values also

have supported the kind of business

performance that can result in solid

shareholder returns over many years.

These beliefs support our confidence

in the company’s present course and

in our ability to deliver value to clients

and to our investors in the years ahead.

Ultimately, we will be judged by our abil-

ity to generate profits and by our stock

price, which clearly does not yet reflect

much of the work we are doing or the

progress we have made.

I want to personally thank Elaine Roberts,

the President of our Holding Company,

who for over 35 years has been a sup-

portive and close associate to me and to

the Company. Elaine will be retiring at the

end of the first quarter but has agreed

to remain as a director. We look forward

to her counsel for many years to come.

Let me close by expressing my appre-

ciation to the Oppenheimer team and

my gratitude to you, our shareholders,

for your unwavering support. I trust

you share our excitement about your

Company’s future and the way in which

we are building on our past to build an

even brighter future.

Albert G. Lowenthal

Chairman of the Board

4

We ended 2012 with over $80 billion

of client holdings entrusted to our

firm, an all time high. During 2012,

we hired 66 experienced Financial

Advisors, adding meaningfully to our

highly capable and well trained staff

of investment professionals.

Low interest rates, extremely low by

historical standards, have created a

challenge for our advisors to provide

investment advice that would gradually

help clients to reallocate their invest-

ments to vehicles and strategies that

would work toward them achieving

longer-term objectives. This includes the

use of alternatives designed to provide

attractive returns compared to those

available in either short- or longer-term

fixed income securities, with the intent

of preserving purchasing power and

with the possibility of future growth.

These investment alternatives include

research-followed equities, equity strat-

egies with attractive dividend returns,

open- and closed-ended mutual funds,

preferred stocks, adjustable-rate secu-

rities and convertibles as well as bonds

and annuities.

We also believe that managed portfolios

offer attractive long-term returns with the

benefit of a dedicated and experienced

money manager, chosen for expertise in

a specific investment sector. Our partner,

Oppenheimer Asset Management, helps

us find the “best of breed” within our

clients’ desired allocation.

Our Chief Investment Strategist, John

Stoltzfus, whose weekly written research

pieces and frequent media appearances

along with regular client meetings pro-

vided direction and context to a complex

investment environment. He has helped

form an effective synergy with our Chief

Market Technician, Carter Worth, in advis-

ing our Financial Advisors and clients.

Professional Development

The Oppenheimer Professional Devel-

opment Department is charged with

ensuring that our Financial Advisors are

positioned to remain current and fully

trained in the rapidly evolving investment

world that we face. Our advisors’ role

has changed to a highly consultative

“counseling” model and they must be

prepared to counsel our most sophisti-

cated clients.

The experience of the last 5 years has

resulted in a recognition by clients and

advisors that they must realign their

priorities. Clients are focusing on basic

financial organization, crafting formal

financial blueprints for their lifetimes,

analyzing household cash flows, looking

more closely at their existing lifestyle

needs and crafting retirement living

strategies that incorporate enjoyable and

meaningful work, along with plenty of

opportunities for family.

Wealth transfer is of keen importance

to clients, concerned to assure that their

accumulated savings can be passed on

to future generations. We see this hap-

pening through meetings and discussions

with clients on a multi-generational

basis. The sure knowledge of higher

taxes has made it all the more important

that we keep our clients in touch with

constructive solutions to this dilemma.

Oppenheimer Trust Company

Oppenheimer Trust Company is a leader

in delivering innovative investment man-

agement, asset and fund administration

and fiduciary services to affluent indi-

viduals, corporations and institutions.

In the midst of change, there is a need

for some things that remain constant.

Today, more than ever, our clients need

a strong foundation and a fiduciary to

rely on as their financial affairs become

more complex.

During 2012, Oppenheimer Trust had

a 31% growth in revenue and a 15%

growth in fiduciary assets under our

management and care. At year-end,

PRIVATE CLIENT SERVICES

Oppenheimer’s Private Client Services area continues to be the

cornerstone of our firm. Our entrepreneurial culture and our focused

business environment has differentiated us from other financial service

providers and allowed us to offer our clients significant flexibility and

solutions that are customized and tailored to their goals, objectives and

unique circumstances.

5

assets held by us stood at $2.2 billion

as we continued to service the fiduciary

needs of clients.

Oppenheimer Life Agency, Ltd.

Oppenheimer’s insurance platform is

designed to offer our clients sophisti-

cated planning techniques that provide

innovative solutions for long-term goals.

In 2012, our annuity platform continued

to focus on guaranteeing clients lifetime

income with variable annuities. Given the

ongoing low interest rate environment,

annuities as well as life insurance are an

asset class which provides protection and

yield to clients planning for retirement.

Our life insurance platform was broad-

ened to assist our Financial Advisors in

focusing not only on the changing tax

landscape and its impact on our clients’

overall estate planning objectives, but to

also educate our clients on the crucial

role life insurance can play in planning.

Our Financial Advisors are able to coun-

sel their clients on life insurance as an

irreplaceable solution to legacy planning.

Advisors are able to address clients’

concerns regarding wealth transfer by

establishing and designing appropriate

plans utilizing life insurance and long-

term care insurance as a part of their

overall investment strategy.

Our advanced executive benefit plat-

form, which includes corporate owned

life insurance, provides our corporate

clients with a means to provide enhanced

wealth-building benefits to their employ-

ees. Oppenheimer continues to stand

out as we offer our corporate clients

innovative employee paid benefit pro-

grams as well as advice to control the

future cost of such benefits.

Executive Services

The Executive Service Group offers a

range of sophisticated strategies to

corporate executives to protect and

enhance the value of their assets. These

individuals are frequently concerned

with the risks associated with concen-

trated portfolios, where employer stock

overwhelms all other assets. The desire

to address this concentration risk may

also be influenced by tax considerations

or by regulatory requirements. Our expe-

rience and advice surround the sale of

stock under SEC Rule 10b5-1 and/or

Rule 144 , as well as a variety of hedging

strategies that may provide qualified

clients with diversification, liquidity and

downside protection. Executive Services

also works with corporate sponsors of

equity benefit plans to help find tailored

and effective solutions.

Retirement Services

The Retirement Services Department

consults with individuals, small employ-

ers and institutions to develop strategies

that will meet investors’ retirement goals.

Various retirement plan designs may be

utilized to help meet both employer and

employee goals in providing retirement

income. Retirement account assets for

Oppenheimer clients increased to over

$20 billion at year-end 2012. The increase

was due in large part to new client assets

in our retirement advisory programs, now

at more than $4.5 billion in assets. As

company-funded pension plans contin-

ue to diminish in importance, our focus

on a process of prudent advice to plan

fiduciaries has helped increase 401(k)

plan advisory assets under management.

Professional Alliance Group

The Professionals Alliance Group (PAG)

supports third-party professional firms

in expanding their businesses by pro-

viding financial services to their clients,

further enhancing the partner’s role as

a trusted advisor. PAG has relationships

with accounting firms, business man-

agers, sports agents, consultants and

other professionals throughout the world

and represents over $2 billion in assets

deposited with our firm.

6

Our investment team, advisory process

and analytical capabilities are the cor-

nerstone of who we are and what we

do. During the past year, we enhanced

our traditional and alternative investment

capabilities. We launched two new hedge

funds and added additional high convic-

tion managers to our recommended list

of traditional managers. Throughout our

history, we have sought to help our clients

invest in specialized, niche areas where we

find investment opportunities managed

by talented investment professionals with

strong credentials.

We are increasingly being called upon

to provide financial planning services for

clients seeking to unify their financial life.

Our effort requires having opinions, views

and ideas developed through an effort

dedicated to proprietary investment

research and market analysis. Our ser-

vices will provide an ongoing program

so that clients can be prepared to fund

education expenses and retirement in a

systematic manner. In coordination with a

client’s Financial Advisor, our profession-

al staff collect the required information

from clients, consult extensively with the

client and ultimately review the results

with the client to ensure that the plan

provides a financial roadmap for them,

both now, and in the future.

Consulting Group

The Consulting Group provides val-

ue-added services in asset allocation,

manager selection, portfolio construc-

tion and manager-of-manager investment

programs. Over the course of 2012, the

Consulting Group continued increas-

ing the number of unique investment

managers and high conviction strategies

offered. Each of these must have the

flexibility and nimbleness to successful-

ly navigate difficult markets. Assets in

the discretionary and non-discretionary

programs exceeded $9 billion.

The fastest growing offerings include the

Portfolio Advisory Service (PAS), a fee-

based mutual fund advisory program and

the Unified Managed Account (UMA) pro-

gram, which allows for multiple investment

managers, mutual funds and/or ETFs to be

ASSET MANAGEMENT

Oppenheimer Asset Management’s mission is to provide investment

advice that best serves the needs and objectives of our clients, to

implement effective solutions and innovative investment strategies

and to protect and grow capital with appropriate risk controls. In 2012,

revenues generated, client accounts serviced and assets ($20.9 billion)

under management reached an all-time high.

7

combined into a single custodial account.

The Managed Allocation Series (MAS),

part of the discretionary offerings available

in separate account or mutual fund struc-

tures, continued its strong growth as well

as excellent risk-adjusted performance for

clients. The MAS portfolios combine the

Consulting Group’s asset allocation, man-

ager research and portfolio construction

philosophy with a dynamic overlay process

designed to respond opportunistically to

changing market conditions.

Oppenheimer Investment Advisers

(OIA)/Oppenheimer Investment

Management (OIM)/ Fahnestock

Asset Management (FAM)

The OIA and OIM investment teams pro-

vide fixed income strategies that share

a common philosophy emphasizing a

disciplined investment process and a long-

term perspective focused on managing

risk. The primary objective is to reduce

risk by focusing on a diversified selection

of higher quality investment-grade bond

issues. OIA and OIM managers have a

broad capability and extensive experi-

ence managing taxable and tax-exempt

investment portfolios. Assets under man-

agement exceed $2.1 billion.

FAM provides a balanced approach to

investing with exposure to both equity and

debt investments. Its experienced man-

agers manage in excess of $700 million.

OIA, FAM and OIM offer clients direct

access to Oppenheimer portfolio man-

agers as well as a customized approach

that allows the creation of a variety of

portfolios to meet specific client needs.

Alternative Investments

The Alternative Investments Group ended

2012 with $2.5 billion in assets under man-

agement across a select number of invest-

ment partnerships. AIG provides alternative

investment research and consulting and

offers single-strategy, multi-strategy and

separate account management for hedge

funds and private equity. In January 2012,

the AIG investment team was strengthened

by the addition of new personnel with

wide-ranging experience and capabilities.

The team reconstituted the existing fund

of hedge funds, the Advantage Advisers

Whistler Fund, to embody their investment

philosophy of finding managers with strong

pedigrees, specialized in a single area of

expertise and a demonstrated ability to

produce above market returns. In addition,

we also launched two niche single strategy

hedge funds, the Chichester Commodities

U.S. Feeder Fund, a relative value commod-

ities fund, and the Susa European Equities

Fund, an equity long short fund focused

on European companies. In 2013, the team

aims to introduce additional new strategies

with an ongoing focus on performance

across all investments.

Advisor-Directed Portfolio

Management

The OMEGA Program of discretionary

portfolio management strategies contin-

ued to grow in 2012. Assets at year-end

stood at over $1.9 billion reflecting 26%

growth for the year. The momentum

behind this trend has been the addition

of experienced Financial Advisor Portfolio

Managers to our firm. These advisors utilize

a variety of investment approaches in their

efforts to achieve consistent returns for

clients over time. The Preference Advisory

program is a non-discretionary, fee-based

advisory program for clients who want to

select their investments with the flexibility

to change investment direction without

additional costs or commissions. Program

assets at year-end were $2.9 billion.

We are increasingly being called upon to provide financial planning services for clients seeking to unify their financial life.

8

Oppenheimer’s Equity Sales and

trading department has continued

to provide the firm’s clients with a

consistent and high quality research

product coupled with a global trade

execution capability. Our trading desks

in New York, London, Boston, Chica-

go, San Francisco and most recently

in Hong Kong continue to serve more

than 1,000 institutional clients around

the world. The Oppenheimer name in

all these markets represents a value

added, alpha generating service offer-

ing that continues to be ranked in the

top 30 financial services firms around

the world.

The Oppenheimer equity franchise contin-

ues to grow and the firm is participating

in an increasing number of equity transac-

tions across multiple industry verticals. As

the world economy stabilizes, we expect

that there will be an increase in investor

appetite for equities in the coming year

and a corresponding increase in all types

of equity activity including IPOs.

Our client base continues to broaden

in the U.S., Europe and Asia and there

is demand from mutual funds, hedge

funds and pension funds for high quality

equity offerings. Oppenheimer has built

its equity distribution platform to focus

primarily on small and mid cap equity

investors giving us a strong opportunity

to underwrite equity offerings in growth

and emerging growth verticals.

During this past year, Oppenheimer

completed over 75 public, private equity

and equity-linked offerings raising an

aggregate of approximately $30 billion

on behalf of our clients. Oppenheimer

was an active book-runner in the Health-

care, Industrial, Energy and Technology

sectors. The firm is renewing its focus

in the Financials Sector where we see

high levels of activity emerging in the

next several years.

While 2012 saw lower volumes in

offerings of Chinese companies,

Oppenheimer has continued to maintain

CAPITAL MARKETS

During 2012, Oppenheimer focused on the need for a robust re-evaluation of our business, and

especially on ensuring our product is being delivered efficiently to a client base that is receptive

and prepared to compensate us for the value we bring to their investment process. Concerns about

the European economy and sovereign debt, coupled with a growing disappointment in the pace of

the recovery in the U.S., kept many investors sidelined throughout the year. The challenge posed by

the deadlock in Washington kept overall volumes low with commissionable volume declining 15%

versus 2011. However, market indices rose throughout the year with large-cap equities, especially

companies with global reach and high dividends as major beneficiaries.

EQUITY CAPITAL MARKETS

9

an active dialogue with potential major

Chinese issuers. We expect that in 2013 we

will see a return of these companies to the

U.S. capital markets as valuations of exist-

ing China listed equities have improved.

The past year was particularly active in

offerings related to the energy sector. New

technology has significantly increased natu-

ral gas and oil production in North America,

which in turn has required ever increasing

amounts of new capital. There has been and

will continue to be record levels of issuance

from energy companies, including those

providing infrastructure, transportation and

production enhancement. As this process

continues, we anticipate broad opportunities

for middle market companies, such as those

for which we can be a significant partner.

Oppenheimer’s Equity Research Depart-

ment continues to provide our clients with

high-quality, differentiated research. At

year-end, our research group consisted

of 34 senior research analysts covering

approximately 600 companies across six

major sectors: Consumer & Business Services;

Energy; Financial Institutions; Health-

care; Industrial Growth; and Technol-

ogy, Telecom & Internet. In addition,

we provide Special Situations research,

as well as Investment Strategy and

Technical research.

As we have become increasingly global,

among U.S. investment banks, we have the

largest coverage of U.S.-listed China based

companies, with three analysts following over

40 companies and new areas of coverage in

the Hong Kong, Singapore, China and India

markets. In London, we will begin offering

specialized research on a top- down basis to

investors looking for additional perspective

on companies based in Europe and trading

exclusively on European markets.

The September 2011 Top Picks portfolio

which launched September 29, 2011

and consisted of each analyst’s top idea

for the following 12-month period gen-

erated a total return of 32%, after fees

and expenses. It outperformed the S&P

500 index by over 600 basis points. The

department has raised over $125 million

to date across the three Top Picks Portfolio

UITs, and will continue to introduce similar

products for clients.

We conducted 11 investor conferences,

providing an in depth look at many aspects

of our research coverage. Over 500 public

and private companies were provided a

forum to meet with approximately 2,000

institutional investors. These events were

accompanied by our robust Corporate

Access program, where we provide com-

panies the opportunity to travel with our

professional staff to meet with institutional

investors in their offices around the U.S.,

London and in Hong Kong. In 2012 we

provided this service to over 500 compa-

nies, which participated in thousands of

meetings around the world.

Looking forward, our attention in the

coming year will be focused on ensuring

Sales and Trading staff are deepening the

penetration of our product with existing

clients, and to broaden the reach of our

product to develop new clients as we

have done in Hong Kong with the addi-

tion of four seasoned Equity professionals

and local research product to the existing

team. We are now covering 13 Asian

markets and are offering Asia Equity

execution to the Firm’s global clients.

Oppenheimer has built its equity distribution platform to focus primarily on small and mid cap equity investors giving us a strong opportunity to underwrite equity offerings in growth and emerging growth verticals.

10

Oppenheimer’s investment banking business

results were led by our mergers and acqui-

sitions practice during 2012. As corporate

clients continued to re-position their business

for a changing global environment, they

engaged Oppenheimer to render actionable

advice and to assist them in executing on

their strategy. Increasingly, middle market

corporate clients and private equity firms

rely on us for advice in our sectors of focus

where we have proven expertise and possess

strong industry knowledge.

The firm acted as strategic financial advi-

sor on 21 mergers and acquisitions, with

a transaction value of $2.7 billion in 2012.

Overall M&A activity in 2012 continued

to be constrained by uncertain macroeco-

nomic conditions. Momentum slowed as

the year progressed, as buyers and sellers

became more cautious. Confidence levels

are increasing, and a stronger econo-

my, a strong stock market and early

announcements of M&A transactions

will continue to stimulate increased M&A

activity throughout 2013.

During 2012, Oppenheimer completed a

number of significant strategic advisory

assignments, including the $635 million

sale of Decision Resources to Piramal

Healthcare Ltd., the $295 million sale of

Things Remembered to Madison Dearborn

Partners, the $240 million sale of Reach

Medical Holdings, Inc. to Air Medical Group

Holdings, Inc., the $193 million sale of Flan-

ders to Insight Equity, the sale of Secure-24

to Pamlico Capital, and the recapitalization

of Connolly, Inc. by Advent International.

During the downturn in the first half of

2012, many non-U.S. publicly-listed com-

panies have looked to “go private;” we

were active in this area as well. With our

full-service suite of capabilities, Oppen-

heimer continues to be a partner of choice.

In the first half of the year, Oppenheimer

was active in supporting our clients in their

issuance of equity securities to the public

markets through initial public offerings and

secondary offerings. We also assisted clients

in the private placement of equity securities.

During the year, Oppenheimer completed

76 public equity offerings and two private

placements, raising approximately $31.3

billion in capital. The firm experienced the

most equity raising activity in the healthcare

and energy sectors. The firm also contin-

ues to build on its capabilities in Asia and

Europe, where it works with companies in

the region to access the U.S. capital markets.

In mid-2012, Oppenheimer formalized its

collaborative relationship with RBS Citizens

Bank to provide Mergers & Acquisitions

and Equity Capital Markets expertise

to RBS Citizens’ middle market clients,

while simultaneously offering credit and

commercial banking solutions from RBS

Citizens Bank to Oppenheimer’s middle

market clients. This relationship leverages

complementary middle market commer-

cial and investment banking products, ser-

vices and expertise and we are optimistic

about the potential of the relationship.

This unique collaboration between Oppen-

heimer and RBS Citizens Bank has result-

ed in several early successes in leveraged

finance situations where Oppenheimer’s

advisory relationships secured significant

financing transactions for RBS Citizens

Bank. Notable transactions in 2012 include

RBS Citizens acting in the Lead Arranger

role in the $105,000,000 financing for

the acquisition of TaxAct by Infospace, a

Co-Lead Arranger role in a $170,000,000

financing for PMC Group in support of

their acquisition of Arkema’s global tin

stabilizer and catalyst business, and the

Lead Arranger role in a $120,000,000

refinancing for Geo Specialty Chemicals.

In 2012, we had a change in leadership

in the Investment Banking Group leading

to a renewed focus on growing the busi-

ness and capitalizing on the dislocation

and uncertainty at many of our investment

banking peers. The new leadership team

has embarked on a number of key initiatives

to drive growth, including: (i) expanding our

coverage and expertise in industry sectors

that we believe will experience significant

growth, (ii) expanding our relationships with

middle-market oriented private equity firms,

(iii) driving alignment with the Equity and

Debt Capital Markets Groups, (iv) leverag-

ing opportunities within our large private

client network, and (v) developing the RBS

Citizens relationship to generate additional

opportunities. Looking forward to 2013, we

believe we are on course to leverage our

key strengths and capitalize on stabilizing

capital markets and increased M&A activity.

INVESTMENT BANKING A Leading Middle Market Investment Bank

10

Selected M&A Transactions

Undisclosed $635,000,000 $295,000,000 $166,175,000 $72,450,000 $120,000,000

Advisor on Recapitalization by

Advent International Exclusive Financial Advisor

Advisor on Sale to Piramal Healthcare Ltd.

Joint Sell Side Advisor

Sale toMadison Dearborn

Partners, LLCExclusive Financial Advisor

Hybrid OvernightFollow-On Offering

Lead Manager

Initial Public OfferingLead-Left Bookrunner

Senior Credit FacilityExclusive Financial

Advisor

July 2012 June 2012 May 2012 February 2012 February 2012 October 2012

Selected Equity & Leveraged Finance Transactions

11

Municipal finance continues to be the

backbone for states, cities and public

entities to continue to serve the needs

of their residents through the con-

struction and rehabilitation of needed

infrastructure and to finance long-term

services. Oppenheimer’s Public Finance

Group operates a business model geared

toward service to clients throughout

the public sector. Oppenheimer offers

a broad suite of services: underwriting

of fixed and variable rate transactions,

placement of short-term notes, finan-

cial advisory services on general market

transactions as well as project finance

to issuers both within and beyond the

mainstream municipal market.

In addition to achieving an all-time high in

gross revenues, the Public Finance Group

made strides in 2012 toward developing

new business strategies that position

bankers to increase the number of trans-

actions and revenue in 2013 and beyond.

These include the opening of four new

offices in Dallas, TX, Fort Lauderdale,

FL, Houston, TX, and Leawood, KS and

collaboration with both Oppenheimer’s

short-term municipal desk and Oppen-

heimer Multifamily Housing & Healthcare

Finance, Inc. Indeed, as several of the

industry’s most prominent public finance

groups have scaled back operations or

shuttered entirely, Oppenheimer has

capitalized on the retrenchment to

strategically add talent.

Public Finance is positioned to achieve

success due to the wide array of expe-

rience and performance spanning a

broad spectrum of sectors and credits.

Oppenheimer’s 2012 transactions reflect

a banking strategy integrating both tra-

ditional governmental issuers and other

transactions, that are tax-exempt by

virtue of the 501(c)3 status of the bor-

rower or a federal tax-exempt allocation.

Education finance continues to be of high

importance to state and local issues. In

2012, Oppenheimer managed over $500

million in education-related debt, ranging

in principal amount from under $500,000

to $65 million. The Topeka office originat-

ed over $50 million on behalf of Kansas

school districts, and the recently opened

Texas office has already begun to finance

independent school districts.

In the Midwest, Oppenheimer had

strong success serving as co-senior

manager of approximately $1.5 billion of

bond issues for the Illinois Department

of Employment Security. In addition,

we again assisted Jackson County,

Missouri to refinance the Truman Med-

ical Center, this year for $39 million.

In addition, Oppenheimer served the

City of Carmel, Indiana, with the sale

of two series of Lease Rental Revenue

Multipurpose Bonds. The bonds were

used to finance a parking facility for a

public building in the City Center and

to restructure the existing debt of the

City and the District.

Oppenheimer served as co-manager on

over $26 billion of bond issues nation-

wide in 2012. Major issuers included the

Dormitory Authority of the State of New

York, the Metropolitan Transportation

Authority, the New York City Transitional

Finance Authority, the State of California

and the County of Los Angeles.

PUBLIC FINANCE

Significant Financings by the Municipal Capital Markets Group in 2012

$1,469,940,000State of IllinoisUnemployment Insurance Fund Building Receipts Revenue Bonds

$185,145,000City of Carmel (Indiana) Redevelopment District Lease Rental Revenue Multipurpose Bonds

$135,000,000Wayne County, MichiganGeneral Obligation Limited Tax Notes

$101,322,000Rockland County, New YorkVarious Purpose Bonds and Revenue Anticipation Notes

$48,244,000Hudson County (New Jersey) Improvement AuthorityCounty Guaranteed Pooled Notes

$46,875,000Jefferson County (Texas) Industrial Development CorporationHurricane Ike Disaster Area Revenue Bonds

$53,190,000Township of Lyndhurst, New JerseyBond Anticipation Notes

$39,025,000Jackson County, MissouriSpecial Obligation Refunding Bonds

$38,800,000Space Coast Infrastructure AgencyInfrastructure Improvement Revenue Bonds

$31,645,000North Kansas City School District No. 74General Obligation Refunding Bonds

Oppenheimer’s Public Finance Group operates a business model geared toward service to clients throughout the public sector.

11

12

The Fixed Income division had another

year of solid performance. While the U.S.

Presidential election, the debt ceiling and

the fiscal cliff provided a colorful backdrop

to the rates and credit markets, the over-

whelming influence on the bond market

was the Federal Reserve QE3 (Quantita-

tive Easing 3) program. Risk Free rates

remained at historic lows and the total

amount of outstanding U.S. Treasury debt

reached record levels once again. U.S.

corporations continued to issue record

amounts of debt at advantageous interest

rates. U.S. home owners continued to

refinance their mortgages at historically

low rates and these low cost attractive

rates began to fuel new construction

and the beginning of a recovery of the

housing market as new levels of afford-

ability opened this critical market to new

participants. In addition to buying by the

U.S. Federal reserve, U.S. private investors

continued to allocate their savings to the

bond market fueling professional money

managers to easily deploy the resulting

fund inflows into bond portfolios across

the spectrum of risk appetite from emerg-

ing market, to high yield, to highly con-

servative U.S. Treasuries.

Investor demand for higher yields led many

buyers to purchase bonds from sovereign

and corporate issuers who had been effec-

tively locked out of the debt markets for

nearly 5 years through lack of investor

demand. Corporations throughout the

emerging and developed world found a

receptive market for their debt, leading to

record new issuance of Emerging Market

corporate debt. As global banks continue

to pull back their financial exposure outside

of their home countries to non-domestic

borrowers, those same borrowers increas-

ingly found the bond market a suitable

replacement. While Oppenheimer does not

focus on Emerging Market bond origina-

tion, we do transact with many domestic

and international clients who are active

participants in the secondary markets.

Oppenheimer consolidated the leader-

ship of the Taxable and Municipal bond

divisions in 2012. This change took effect

mid-year and has already resulted in the

rationalization of some duplicative costs.

We also created a growing number of

revenue enhancing synergies as a result of

the combination. During the year, we set

the stage for new growth in this import-

ant market by adding additional municipal

traders, sales people and public finance

bankers. While these new capabilities are

already contributing to the profitability

of the division, we anticipate that these

enhancements will lay the groundwork

for further expansion in the coming years.

By staying attuned to news and events

in the municipal markets, we were able

to find opportunities to find real value

for clients as “bad news” for some issu-

ers was misinterpreted by the markets

and presented unusual value to “smart

buyers” with an ability to understand

how fragmented the municipal market

can be with neighboring issuers having

completely different credit profiles. Such

opportunities have prompted us to begin

offering municipal research specializing in

opportunity investing as well as services

to advise municipal investors on portfo-

lio construction and on the attraction of

taking advantage of “swaps” to increase

yield and shorten duration and better

position portfolios for a rising interest

rate environment.

We continued to expand the number of

Fixed Income accounts covered and were

able to improve our overall market share

across all fixed income asset classes. This

was accomplished through our hiring of

experienced sales, trading and research

personnel, while maintaining our com-

mitment to providing clients with high

quality service and market leading ideas.

DEBT CAPITAL MARKETS Fixed Income Sales, Trading and Research

13

Our client-facing business model insulated

us from the risks associated with extreme

volatility and market exposures often asso-

ciated with large proprietary trading desks.

The expected near term effectiveness of

the Volcker Rule, which severely curtails

proprietary trading by banks, will not

impact Oppenheimer’s business because

we continue to operate as a broker and

a dealer, and not as a commercial bank.

Our business remains primarily focused

on servicing our clients with value added

research and conflict-free trading capabil-

ities. Our ability to offer execution across

broad areas of fixed income, including U.S.

Government and Agency debt, high grade

corporate debt, mortgage debt, high yield

corporate debt, emerging market debt

and preferred shares, is unique among

our competitors. Given our relationship

with Oppenheimer Multifamily Housing

& Healthcare Finance, we effectively and

promptly distributed over $1 billion in new

issues of FHA insured securitized debt

in 2012.

While we deal with larger institutions on

a regular basis, the majority of our institu-

tional clients are “middle market” accounts

and thus remain largely underserviced by

our larger competitors. The high level of

service we provide to these clients has won

us a dedicated and loyal base and permits

us to earn the opportunity to fill many

of their needs. In 2012, we continued to

build our business by hiring experienced

professionals located throughout the

United States, as well as in London, Tel

Aviv and Hong Kong.

Although the domestic financial markets

have generally recovered from the credit

crisis, many large firms have been forced

by the upcoming Volcker Rule to priori-

tize their origination efforts and curtail

proprietary risk activities. This has created

a void in the market that Oppenheimer is

uniquely positioned to serve. Additionally,

small boutiques that were once considered

safe harbors during the crisis are increasingly

challenged in the new environment. With-

out capital, research or a diversified mix of

clients and trading capabilities, these firms

have had difficulty maintaining the attention

of large institutional clients. Our focus on

middle market customers and niche trading

capabilities continues to be an advantage

in the post credit crisis environment.

Oppenheimer Europe

Oppenheimer continued to grow its

fixed income franchise outside the

United States. With an increase in the

size of our fixed income trading group

in London and our newly opened facility

on the island of Jersey, we believe that

we can continue to grow our business.

Our growth will be sourced in the UK as

well as the rest of Europe through our

unique ability to service inquiries from

institutions requiring higher levels of

service and attention.

Oppenheimer Asia

In Asia, we hired new leadership on the

trading desk in Hong Kong. We have since

made significant progress in generating

consistent revenue and profitability. We will

continue to recruit talented professionals in

Hong Kong and through a small dedicated

staff, we intend to continue focusing on

offering Asian owners and issuers of debt

access to niche markets in Europe, the U.S.

and Asia.

DEBT CAPITAL MARKETS Fixed Income Sales, Trading and Research

14

As a leading commercial mortgage

banker, we provide customers with a

full range of services such as origination,

underwriting, closing, securitizing and

servicing of their mortgage loans.

In 2012, we closed 97 loans for just under

$900 million. These loans represented

a wide range of properties including

apartments, hospitals and healthcare

facilities. Fiscal 2012 saw us among the

top five lenders for FHA Multifamily Ini-

tial Endorsements and the top 10 of all

lenders of for FHA Firm Commitments.

Our servicing portfolio increased by

36.4% from 2011 to 2012. We faced

increased competition to refinance loans

from the existing OMHHF portfolio. Pro-

actively, we identified all loans eligible for

refinance and contacted those borrowers

well in advance. As a result, we were

able to keep a high percentage of the

refinanced loans.

Another advantage is our ability to collab-

orate with other Oppenheimer divisions to

cross-sell products, with the opportunity

to raise capital from the equity markets

or through healthcare financing in the

municipal market. These products create

additional value for Oppenheimer’s clients.

We continue to pursue correspondent

relationships to leverage our infrastructure

while sharing revenue with well established

unrelated mortgage bankers.

We find we are able to create addition-

al efficiencies and economies by using

OMHHF team members to perform all

necessary services in-house. We were

helped in this effort by Oppenheimer’s

name and reputation. Both proved attrac-

tive to the seasoned candidates whom we

successfully brought on board in all areas

of our business, including Originations,

Underwriting and Servicing.

Another ongoing challenge is the

impact of rapid technological growth

on our business. Our customers’ need

for more information more quickly can

only increase. We are stepping up our

efforts to devise real-time, automated

methods of providing these data on a

robust and secure platform.

Going into 2013, we continue to

pursue relationships with firms that

can provide our clients with the abil-

ity to finance commercial properties

with non-FHA financing alternatives to

expand our ability to provide one-stop

shopping. We intend to also sell other

Oppenheimer products to eligible and

interested clients.

Representative Properties

Financed by OMHHF in 2012

Ellis Hospital 2 New York$54,850,000

Lebanon Ridge Texas$31,474,800

Hawthorne Hill Colorado$28,240,000

Shores at K-Rock Oklahoma $28,119,500

Amberleigh Shores North Carolina$26,560,500

Bethel Health & Rehabilitation Center

Connecticut$26,268,700

Sunlake at Edgewater Apartments

Alabama$21,000,000

Wembly at Overlook

Georgia$20,427,800

Waterford Park Apartments

Texas$16,479,600

COMMERCIAL MORTGAGE BANKING

Oppenheimer Multifamily Housing & Healthcare Finance (OMHHF) is a

licensed FHA mortgagee and GNMA Seller/Servicer. Its role is to assist

owners of multifamily apartment properties and healthcare facilities,

including nursing home and assisted living properties, to employ a

government-assisted mortgage program in financing or re-financing

their mortgages cost effectively.

Bethel Health & Rehabilitation Center, Connecticut

15

Our Annual Report on Form 10-K for the year ended December 31, 2012 also serves as

our 2012 Annual Report to Stockholders. It is available to view and print online on our

website at www.opco.com on the Investor Relations page. A stockholder who wants

to receive a paper or email copy of our Annual Report on Form 10-K for the year

ended December 31, 2012 must request one. The report is available, without charge,

except for exhibits to the report, by (i) writing to Oppenheimer Holdings Inc., 85

Broad Street, 22nd Floor, New York, New York 10004, Attention: Secretary, (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 reasonable fee.

16 | Oppenheimer Holdings Inc.

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Branch Offices (U.S.)

Oppenheimer Holdings Inc. | 17

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Capital Markets Offices (International)

Hong Kong, ChinaOppenheimer Investments Asia Limited Henley BuildingUnit 1001No 5 Queens Road CentralHong Kong852-3658-7368

Beijing, ChinaFreedom Investments Inc., Beijing Representative Office Units 29-30, 26th Floor, China World Office 1 The China World Trade Center No. 1 Jian Guo Men Wai Avenue Chaoyang District, Beijing 100004 China +86 (10) 6505-9884

London, EnglandOppenheimer Europe, Ltd. 6 Gracechurch Street1st FloorLondon EC3V 0ATUnited Kingdom44-207-220-1900

Channel Islands, Jersey Branch Oppenheimer Europe Ltd. 43 Hilgrove StreetSt Helier JE2 4SLUnited Kingdom44-153-460-3107

Tel Aviv, IsraelOppenheimer Israel (OPCO) Ltd.Top Tower, 50 Dizengoff StreetPOB 23722 Tel Aviv 61236Israel972-3-526-2666

Principal OfficesOppenheimer Holdings Inc.85 Broad StreetNew York, NY 10004(212) 668-8000FAX (212) 943-8728info@opco.com

Oppenheimer & Co. Inc.Corporate Headquarters85 Broad StreetNew York, NY 10004(212) 668-8000FAX (212) 943-8728

Capital Markets85 Broad StreetNew York, NY 10004(212) 856-4000www.opco.com

Oppenheimer AssetManagement Inc.85 Broad StreetNew York, NY 10004(212) 907-4000FAX (212) 907-4080www.opco.com

Oppenheimer TrustCompany18 Columbia TurnpikeFlorham Park, NJ 07932(973) 245-4635FAX (973) 245-4699www.opco.com

OPY Credit Corp.85 Broad StreetNew York, NY 10004(212) 885-4489FAX (212) 885-4933

Freedom Investments, Inc.375 Raritan Center ParkwayEdison, NJ 08837(732) 934-3000FAX (732) 225-6289

Oppenheimer MultifamilyHousing & Healthcare Finance1180 Welsh Road, Suite 210North Wales, PA 19454(215) 631-9151FAX (215) 412-4583

Photography by Lisa Houlgrave and John Madere

OfficersA.G. LowenthalChairman of the Boardand Chief Executive Officer

E.K. RobertsPresident and Treasurer

J.J. AlfanoExecutive Vice President and Chief Financial Officer

D.P. McNamara, Esq.Secretary

Board of DirectorsR. CrystalG

W. Ehrhardt*°M. Keehner*°G

A.G. LowenthalK.W. McArthur*A.W. Oughtred°G

E.K. Roberts

* members of the audit commit-tee

° members of the compensation committee

G members of the nominating/corporate governance commit-tee

Auditors

PricewaterhouseCoopers LLP

Registrar and Transfer AgentComputershare Shareholder Services LLC480 Washington Blvd,AIMS 074-29-135Jersey City, NJ 07310

The Company’s financial information and press releases are available on its website, www.opco.com, under “Investor Relations”.

A copy of the Company’s AnnualReport on Form 10-K is available by request from info@opco.com

Oppenheimer Holdings Inc.

Corporate Headquarters85 Broad StreetNew York, NY 10004