LEON COOPERMAN
The Goldman Sachs partner who left to beat the market for 25 years straight — and became famous for writing angry letters to presidents.
Leon Cooperman grew up in the South Bronx, the son of a plumber, and turned a scholarship to Columbia Business School into a 25-year run at Goldman Sachs that ended with him running the whole asset management division. Then he started his own hedge fund and beat the S&P 500 for most of the next two decades. He's also the guy who wrote an open letter to Barack Obama in 2011 comparing the president's rhetoric to class warfare — which tells you everything about the man's willingness to pick a fight. In 2016, the SEC charged him with insider trading; he settled for $4.9 million without admitting wrongdoing, which he's never stopped being furious about. The South Bronx kid who made $2.5 billion does not like being told he cheated.
Net Worth
$2.5 billion
Nationality
American
Time Horizon
Long-Term
Risk Appetite
7 / 10
Fund
Omega Advisors Inc.
Net Worth Context
- · Still a billionaire — just the quiet kind at the end of the table.
CAREER & BACKGROUND
Leon Cooperman was born in 1943 in the South Bronx to a Polish immigrant father who worked as a plumber. The family had no money.
Leon delivered groceries and worked every odd job he could find. He got into Hunter College in New York on merit, graduated in 1964 with a degree in business administration, and then did something nobody in his family had done before: he applied to Columbia Business School and got in.
He graduated from Columbia in 1967 and joined Goldman Sachs, which at the time was still a partnership, not a publicly traded firm. He started in the research department and became known for something unusual: he was incredibly specific.
His stock calls came with detailed numbers, not vibes. He worked his way up to become a general partner and eventually chairman and CEO of Goldman Sachs Asset Management — the division that managed money for wealthy clients and institutions.
In 1991, after 25 years at Goldman, he left to start Omega Advisors. The name was almost comically modest for what it became.
He launched the fund with around $450 million, mostly from Goldman connections and his own capital, and proceeded to generate double-digit returns for most of the next two decades. By the mid-2000s, Omega was managing over $10 billion.
In 2016, the SEC accused him of trading on material non-public information about Atlas Pipeline Partners in 2010. Cooperman denied it loudly and publicly.
He hired aggressive lawyers and fought hard. Eventually he settled for $4.9 million — less than 0.2% of his net worth at the time — and a cease-and-desist order.
He agreed to pay but admitted nothing. He's been talking about it in interviews ever since.
In 2018, he announced he would convert Omega from a hedge fund to a family office, returning outside investors' capital. He cited the regulatory burden and the impossibility of generating alpha in a crowded market.
He kept managing his own money and a small circle of trusted investors. At his peak, he was one of the most respected fundamental stock pickers in the business.
He still does media appearances. He still picks stocks.
He still writes letters.
COMPANIES & ROLES
Omega Advisors was Cooperman's main act for nearly three decades. He launched it in 1991 with roughly $450 million and grew it to over $10 billion at its peak.
The fund ran a long/short equity strategy — meaning it bet on stocks going up AND occasionally bet on stocks going down — with a strong bias toward long positions in undervalued companies. Cooperman was a value investor at heart, but not a rigid one.
He'd buy growth companies if the valuation was right and the business was durable.
Before Omega, Cooperman spent 25 years at Goldman Sachs, where he rose to run Goldman Sachs Asset Management. That role put him in charge of billions in client assets and gave him the institutional network he'd later use to seed his own fund.
He was one of the first Goldman partners to leave and immediately start a competing asset management firm — which tells you about both his confidence and Goldman's culture at the time.
Today, Omega operates as a family office rather than a hedge fund. Cooperman manages his own considerable fortune and has signed the Giving Pledge, committing to donate more than half his wealth to charity.
He's given heavily to education — his alma maters, Columbia and Hunter, plus schools in the South Bronx where he grew up. He's also backed medical research and various Jewish philanthropic causes.
INVESTING STYLE & PHILOSOPHY
Cooperman is a bottom-up, fundamental value investor. That means he ignores macro predictions — he doesn't try to guess where interest rates are going or whether the economy will grow — and instead looks at individual companies one by one.
He wants to know: what is this business actually worth, and what am I paying for it?
His framework is simple on paper and hard in practice. He wants businesses trading at a discount to their intrinsic value — basically, companies the market is undervaluing for some reason, whether that's temporary bad news, a misunderstood business model, or just neglect.
Then he wants a reason why the gap will close: a catalyst. Maybe earnings will recover.
Maybe an activist investor is pushing for change. Maybe the company is about to spin off a division that the market has completely ignored.
Think of it like buying a house. You don't just want a house that's cheap — you want a cheap house in a neighborhood that's about to get better, or one that needs work you know how to do, or one with a tenant who's about to move out so you can sell it.
The price is only half the equation. The catalyst is the other half.
Cooperman is not afraid to concentrate. He doesn't run 200 positions to spread risk around.
He builds conviction, does the homework, and bets big on a smaller number of names. In his Omega days, his top ten positions would often represent 40–50% of the portfolio.
That's a lot of eggs in specific baskets — and it means you'd better be right more than you're wrong.
He's also notably comfortable with complexity. He bought distressed debt, energy companies in commodity cycles, banks during crises.
He doesn't stick to simple, clean businesses the way Buffett does. He goes where the math tells him to go, even if the story is messy.
THE PLAYBOOK
Risk Approach
Cooperman thinks about risk the way a plumber's son thinks about money — practically and without illusions. He does not believe in risk-free returns, and he does not believe in diversification as a substitute for analysis.
If you haven't done the homework, owning 100 stocks doesn't protect you. It just means you'll lose money more slowly.
He's talked openly about concentration risk. He accepts it deliberately.
When he's convinced a stock is worth significantly more than it's trading at, he buys a lot of it. If he's wrong, it hurts.
He's been wrong. He's absorbed the pain and moved on.
That's part of the job.
He does not use excessive leverage. He never built Omega into a machine that borrowed three dollars for every one of its own — the kind of leverage that turns a 20% drawdown into an existential crisis.
His long/short book was partially a hedge, but he's always said the shorts were more about opportunity than pure protection. He's not a tail-risk obsessive.
On the regulatory side, the SEC case clearly shook him. Whether he was guilty or not — and he says he wasn't — having the government investigate your trading changes how you think about operational risk.
He returned outside capital partly because the compliance burden on hedge funds became too heavy relative to the advantages. That's a form of risk management too: knowing when the structure of your business has become a liability.
Money Habits
Cooperman still lives in New Jersey, not far from where he built his career. He's not a flashy spender.
He doesn't have a fleet of yachts or a Gulfstream profile that screams new money. His philanthropy has been the main story of his spending in later life — he's given over $200 million to charity and counting, including major donations to Columbia University's medical center (renamed after him), Hunter College, and schools in the South Bronx where he grew up.
He drives his own car. He's been photographed at Applebee's.
He is the kind of guy who made $2.5 billion and still talks like a guy from the Bronx, because he is. That's not performance — his whole persona is grounded in where he came from and the work ethic it took to get out.
He's signed the Giving Pledge, Buffett's campaign to get billionaires to donate the majority of their wealth. He takes it seriously.
His donations are primarily in education and healthcare, and they tend to go to institutions that helped people like him — scholarship kids, city college attendees, first-generation professionals. The giving is personal, not strategic.
There's no 'Leon Cooperman brand' being built around his philanthropy.
He's 81 years old and still doing media appearances, still talking about individual stocks, still getting irritated about politics. He has not retired from thinking about money.
He probably never will.
BIGGEST WIN
His best run was the early years of Omega — from 1991 to roughly 2008. In that period, Omega reportedly returned an annualized 12–15% net of fees, consistently beating the S&P 500.
For a long-only-biased fund in a volatile market that included the dot-com crash and the early 2008 crisis, that's exceptional. The compounding over nearly two decades turned the original $450 million seed into a multi-billion dollar fund.
One of his most celebrated individual calls was his deep dive into energy and financial stocks in the early 2000s, when both sectors were undervalued and misunderstood. He bought early and held while Wall Street stayed skeptical.
When the energy supercycle took off in the mid-2000s, his positions paid out massively.
He's also pointed to his identification of Atlas Pipeline Partners in 2010 — ironically the same position that led to the SEC case — as a textbook example of his process. He believed the stock was significantly undervalued, he bought a large position, and he made money on it.
That he was then accused of improper information-gathering on that specific trade became one of the defining ironies of his career.
BIGGEST MISTAKE
The Atlas Pipeline/SEC case is the obvious answer, and Cooperman would hate you for saying that, because he doesn't think he made a mistake — he thinks the SEC was wrong. But even if you take him at his word, the episode cost him $4.9 million in the settlement, years of legal fees, enormous reputational damage, and — almost certainly — played a role in his 2018 decision to convert Omega to a family office.
The indirect cost was far larger than the settlement.
The more financially concrete mistake was his positioning during 2015–2016, when Omega suffered significant drawdowns — reportedly in the range of 20–25% over the period. He was long energy stocks and value names at a time when the market was rotating hard toward growth and momentum.
He misjudged how long the rotation would last and how brutal the oil price collapse would be. A 25% drawdown in a hedge fund managing $10 billion is approximately $2.5 billion in lost value.
He recovered some of it, but never fully made back the ground.
He was also, by his own acknowledgment, slow to see the structural shift toward passive investing and how it would depress returns for active managers across the board. He built a business model that assumed the active management premium would hold.
It didn't hold as well as he expected, and his industry suffered for it.
FINANCIAL PHILOSOPHY
Cooperman's core philosophy is that the stock market is a weighing machine in the long run, even if it's a voting machine in the short run. That's a Buffett/Graham line, and he means it.
Prices eventually converge on value. The job is to find the gaps and wait.
He believes active management can beat the market — and says that claim is proven by his own record — but he also knows that most active managers don't. The difference, in his view, is work.
Real work. Reading 10-Ks at 11pm.
Building spreadsheets. Calling competitors and suppliers to stress-test management's claims.
Most people who call themselves investors are really just allocators with opinions. Cooperman thinks the people who do the most homework usually win.
He's deeply skeptical of passive investing as a long-term cultural trend. He thinks indexing creates dangerous distortions — when everyone buys the index, the biggest stocks get bigger regardless of their fundamentals, and small, genuinely cheap companies get ignored.
That's actually an opportunity if you're willing to do the work.
On wealth: he doesn't believe rich people should apologize for making money legally and paying their taxes. He's had very public disagreements with politicians — most famously Barack Obama in 2011 — over what he sees as demonization of the wealthy.
He is a Democrat who became increasingly hawkish on capital gains taxes and what he calls 'class warfare rhetoric.' His giving is part of the philosophy too. He thinks wealthy people have a responsibility to give back, but on their own terms, not because a politician told them to.
FAMILY & PERSONAL LIFE
Cooperman has been married to Toby Cooperman for over 55 years. She's been a consistent presence in his public life and is reportedly involved in their philanthropic work.
They have two sons.
His roots in the South Bronx are central to his identity. His father was a Polish immigrant plumber — a fact Cooperman returns to constantly in interviews, because it grounds his entire narrative.
He didn't inherit money. He didn't have connections.
He had a scholarship and an aggressive work ethic.
He's talked about his father with obvious respect and emotion. The donations to South Bronx schools aren't just charity for him — they're personal.
He was that kid. He knows what the difference between a scholarship and no scholarship looks like in a person's life.
The family name is on Columbia's medical center now. That's not a small thing for the son of a plumber from the Bronx.
He seems to know it.
EDUCATION
Cooperman graduated from Hunter College in New York in 1964. Hunter was a free public college at the time — literally no tuition — and he needed it.
He studied business administration.
He then got into Columbia Business School, graduating in 1967. That was the credential that opened Goldman Sachs.
Columbia's MBA program at the time was one of the best pipelines into Wall Street, and he used it exactly that way. He's given back to both institutions heavily — Hunter received a major gift, and Columbia's medical center now bears his name.
He clearly believes in the power of public education to change trajectories, because it changed his.
BOOKS & RESOURCES
Cooperman hasnt written a book, which is notable for a man with as much to say as he has
He's given enough interviews and CNBC appearances that you could probably construct one — but no book exists
's 'The Intelligent Investor' is the obvious starting point — the framework of intrinsic value and margin of safety is basically the skeleton of everything Cooperman built his career on. If you want to understand how he thinks, start there
's 'More Money Than God' is as good as it gets — a journalist's history of the hedge fund industry that profiles the major players and explains how the game actually works
As an Amazon Associate, Netfigo earns from qualifying purchases. Book links above may be affiliate links.
QUOTES (6)
I've had a great life and I've worked very hard. I don't think that working hard is something to apologize for.
The stock market is not a casino. It's a place where you can participate in the growth of the American economy if you do your homework.
I grew up in the South Bronx, the son of a plumber. I never thought I'd have the opportunities I've had. That's why I give back.
You make money in the stock market by buying things that are undervalued relative to what they're worth and having the patience to wait for the gap to close.
The biggest risk in investing is not volatility. It's permanent loss of capital. Those are very different things and most people confuse them.
I'm a Democrat. I voted for Obama. But I didn't think it was right to use language that appealed to the baser instincts of the less successful.
NETFIGO SCORE
Proprietary 5-dimension investor rating
Risk Appetite
Contrarian Index
Track Record
Accessibility
Time Horizon
Related Profiles
Investors
David Einhorn
Both are prominent value-oriented hedge fund managers who rose to prominence in the 1990s and 2000s running long/short equity funds, and both have been vocal critics of market structure and regulatory overreach.
Seth Klarman
Cooperman and Klarman both follow the Graham-and-Dodd value investing tradition — bottom-up, fundamental, margin-of-safety driven — and both converted their funds to more restricted structures as the hedge fund industry became more complicated.
Stanley Druckenmiller
Druckenmiller and Cooperman are contemporaries who built legendary track records in the same era and both eventually moved away from managing outside capital, preferring to run family offices in later career.
Head-to-Head
Compare Leon Cooperman vs another investor.