Legendary trades from Soros, Burry, and Paulson show how event-driven strategies create massive profits in market crises.
Sectors & Industries
October 2, 2025
Table of Contents
What does it take to pull off the greatest trade of all time? Some of history’s biggest financial wins weren’t just about picking the right stock. They were about spotting the right event—and acting with conviction before the rest of the world caught on.
From shorting bubbles to buying distressed assets, here are the most legendary trades ever made—and what they teach us about timing, risk, and opportunity.
In 2000, while most of Wall Street was high on tech optimism, Sir John Templeton, then in his late 80s, took a very different stance. He shorted a basket of 84 internet stocks with roughly $2–3 million in capital—just weeks before the crash.
By late 2002, the NASDAQ had fallen more than 75%, and Templeton had already closed his position, walking away with around $80 million—a return of more than 2,500%.
“The four most dangerous words in investing are: This time it’s different.” —Sir John Templeton
Chanos, founder of Kynikos Associates, didn’t buy the hype surrounding Enron. He dug deep into the company's financials and discovered off-balance-sheet liabilities and fake trading revenue. His fund shorted about $60–70 million worth of Enron stock.
When Enron collapsed in December 2001, Chanos walked away with roughly $500 million, an estimated 700% return.
In one of the most well-timed trades in history, Paul Tudor Jones saw the storm forming in 1987. He shorted equity futures before the crash, allocating about $100 million—and then rotated into bonds as markets cratered on October 19.
His fund tripled that year, and Jones personally made around $100 million. This performance solidified his reputation as a hedge fund titan.
Legendary trader Jesse Livermore made his mark during the 1929 crash. He shorted the market just before the collapse, reportedly using $10–15 million in capital.
As the market imploded, Livermore’s positions earned him an estimated $100 million—a 600%+ return and worth more than $1.5 billion today. His story remains immortalized in Reminiscences of a Stock Operator.
At the height of the 2008–2009 financial crisis, most investors were fleeing banks. David Tepper saw a once-in-a-lifetime value opportunity. Believing the government would prevent a total collapse, he bought $1 billion worth of distressed financial stocks like Citigroup.
By the end of 2009, Tepper’s fund gained 120%, profiting over $7 billion. Tepper personally made $4 billion that year, proving the biggest wins often come in the darkest moments.
In the heat of the 2011 U.S. debt-ceiling crisis, Buffett saw another chance. He invested $5 billion into Bank of America, receiving preferred shares with a 6% dividend and warrants to buy 700 million shares at $7.14.
By 2017, those warrants were worth more than $20 billion, marking one of Buffett’s most profitable trades ever—with an over 300% return.
In February 2020, as COVID fears began to spread, Bill Ackman made one of the fastest trades in history. He spent $27 million on credit-default swaps (CDS) to hedge his portfolio.
Within weeks, when markets tanked in March, those CDS positions were worth $2.6 billion—a mind-blowing 9,500% return in less than 30 days.
On September 16, 1992, George Soros bet big that the British pound was unsustainable inside the European Exchange Rate Mechanism. He built $10 billion in leveraged short positions against the pound.
When the UK government devalued the currency, Soros pocketed $1 billion in a single day—a 10% return on huge scale. The trade became known as "The day Soros broke the Bank of England."
While the world celebrated the housing boom, Michael Burry was reading through thousands of subprime mortgage documents. He spotted a pattern of high-risk adjustable-rate loans set to default.
Burry convinced banks like Goldman Sachs to create custom credit-default swaps against these loans. Over two years, he paid about $100 million in premiums, while everyone called him crazy.
In 2007, the mortgage market collapsed—and Burry’s fund, Scion Capital, earned $700 million. Burry personally made $100 million, a 600% return that became the centerpiece of The Big Short.
If Burry lit the fuse, John Paulson detonated the bomb. He launched the Paulson Credit Opportunities Fund, using about $500 million in CDS premiums to short subprime housing at scale.
His funds earned an estimated $15 billion in profits, with Paulson personally making $4 billion in 2007 alone. With an approximate 3,000% return, many still call it “the greatest trade of all time.”
From Black Monday to Black Wednesday, from housing crashes to government bailouts—these trades weren’t just about skill. They were about recognizing an event before the rest of the market did.
Each legendary trade was sparked by:
These were event-driven trades—the same kind that continue to create outsized returns today.
You don’t need George Soros’s bankroll or Michael Burry’s research team to trade the next big market event.
LevelFields AI scans 30,000+ documents per minute—press releases, 8-Ks, SEC filings, economic data, and corporate announcements—to detect the exact types of events that sparked the greatest trades of all time.
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Whether it’s:
LevelFields surfaces those catalysts and delivers them straight to your dashboard, with historical win rates and performance stats to guide your next move.
Watch the The Greatest Trades of All Time video here:
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