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Hall of Legends

The greatest trades in history range from John Paulson's $15B bet against subprime mortgages in 2007 to George Soros's $1B short of the British pound in 1992. Below are 25 legendary trades ranked by profit, spanning decades of market history.

The greatest bets, shorts, and plays in market history

25
Legendary Trades
$193.1B
Total Profit
23
Traders Featured
9
5-Star Legends
16
Still Active
1920s
1
trades
$100M
1980s
5
trades
$101.6B
1990s
2
trades
$2.0B
2000s
11
trades
$45.8B
2010s
2
trades
$17.0B
2020s
4
trades
$26.6B
📈 Long: 9
📉 Short: 7
🌍 Macro: 4
⚖️ Arbitrage: 3
🎰 Options: 2

Ranked by Profit

#1
Jim Simons RETIRED
The Medallion Fund (1988)

Renaissance Technologies' Medallion Fund averaged 66% annual returns before fees from 1988-2018. The greatest sustained trading performance in history. Simons was a former NSA codebreaker.

⚖️ ARBITRAGE Multi-asset quant ⭐⭐⭐⭐⭐
$100.0B
profit
#2
Ken Griffin ACTIVE
Citadel's 2022 Record Year (2022)

Citadel made $16B in net gains in 2022 — the most profitable year by any hedge fund ever. Griffin started trading from his Harvard dorm room with a satellite dish on the roof.

⚖️ ARBITRAGE Multi-strategy ⭐⭐⭐⭐
$16.0B
profit
#3
John Paulson ACTIVE
The Greatest Trade Ever (2007)

Bet against the entire subprime mortgage market using credit default swaps. His fund made $15B in a single year while the financial system collapsed around him.

📉 SHORT CDS on subprime MBS ⭐⭐⭐⭐⭐
$15.0B
profit
#4
Ray Dalio RETIRED
2008 Crisis Navigation (2008)

Bridgewater's Pure Alpha fund returned 9.4% in 2008 while the S&P dropped 37%. Dalio had positioned into Treasuries and gold. His 'Beautiful Deleveraging' thesis proved exactly right.

🌍 MACRO Bonds, gold, TIPS ⭐⭐⭐⭐
$14.0B
profit
#5
Warren Buffett ACTIVE
Bank of America Bailout (2011)

Invested $5B in Bank of America preferred shares with warrants during the 2011 panic. By 2017, the position was worth $17B. Classic Buffett: be greedy when others are fearful.

📈 LONG BAC preferred shares + warrants ⭐⭐⭐⭐
$12.0B
profit
#6
Izzy Englander ACTIVE
Millennium Management's Machine (2022)

Millennium made $8B in 2022 while most funds lost money. Englander's pod-based multi-strategy model has become the template for modern hedge funds. Virtually no down years since founding.

⚖️ ARBITRAGE Multi-strategy ⭐⭐⭐⭐
$8.0B
profit
#7
David Tepper ACTIVE
The Bank Recovery Bet (2009)

Bought massive positions in beaten-down bank stocks and distressed financial debt in early 2009. His fund returned 132% that year. Made $4B personally — one of the best single-year performances ever.

📈 LONG Bank stocks & distressed debt ⭐⭐⭐⭐⭐
$7.0B
profit
#8
Chris Sacca RETIRED
Early Twitter & Uber Investments (2011)

Former Google employee who became one of the most successful angel investors ever. Early bets on Twitter and Uber turned a few million into an estimated $5B+ fortune.

📈 LONG TWTR + UBER pre-IPO equity ⭐⭐⭐⭐
$5.0B
profit
#9
Warren Buffett ACTIVE
Goldman Sachs Rescue (2008)

Invested $5B in Goldman Sachs at the peak of the 2008 crisis. Got 10% dividend plus warrants to buy shares at $115. Goldman paid him back with a $500M premium. Total profit: $3.7B.

📈 LONG GS preferred shares + warrants ⭐⭐⭐⭐
$3.7B
profit
#10
Bill Ackman ACTIVE
The COVID Hedge (2020)

Spent $27M on credit protection in February 2020 as COVID fears mounted. Within 3 weeks, those positions were worth $2.6B. Went on CNBC crying about the apocalypse while his hedge printed.

🎰 OPTIONS CDS / credit protection ⭐⭐⭐⭐
$2.6B
profit
#11
John Arnold RETIRED
Natural Gas Domination (2006)

Former Enron trader who started Centaurus Energy. Made billions trading natural gas futures, including massive profits during the Amaranth collapse. Retired at 38 to become a philanthropist.

🌍 MACRO Natural gas futures ⭐⭐⭐⭐
$2.0B
profit
#12
George Soros RETIRED
Breaking the Bank of England (1992)

Shorted $10B worth of British pounds, forcing the UK out of the European Exchange Rate Mechanism on 'Black Wednesday.' Earned the title 'The Man Who Broke the Bank of England.'

🌍 MACRO GBP short ⭐⭐⭐⭐⭐
$1.0B
profit
#13
Stanley Druckenmiller ACTIVE
Soros's Right Hand (1992)

Actually conceived the British pound trade that Soros gets credit for. Druckenmiller pitched it, Soros told him to make it bigger. Never had a losing year in 30 years of managing money.

🌍 MACRO GBP short + German bonds ⭐⭐⭐⭐⭐
$1.0B
profit
#14
Mark Baum (Steve Eisman) ACTIVE
FrontPoint Subprime Short (2007)

Immortalized as Mark Baum in The Big Short (played by Steve Carell). Eisman's FrontPoint Partners shorted subprime mortgage bonds and made over $1B. Famous for his rage at Wall Street corruption.

📉 SHORT CDS on subprime MBS ⭐⭐⭐⭐
$1.0B
profit
#15
Peter Thiel ACTIVE
The Facebook Bet (2004)

Invested $500K as the first outside investor in Facebook in 2004 for a 10.2% stake. By the IPO in 2012, his shares were worth over $1B. Held some shares even longer.

📈 LONG META (Facebook) pre-IPO equity ⭐⭐⭐⭐
$1.0B
profit
#16
Michael Burry ACTIVE
The Big Short (2007)

A former neurologist-turned-hedge-fund manager who saw the housing crisis coming years early. Endured massive client pressure and margin calls before being proven spectacularly right.

📉 SHORT CDS on subprime MBS ⭐⭐⭐⭐⭐
$800M
profit
#17
T. Boone Pickens RETIRED
Gulf Oil Takeover Bid (1984)

Launched a hostile bid for Gulf Oil, which was 10x the size of his own company. Even though the bid failed, he forced a sale to Chevron and walked away with $760M in greenmail profits.

📈 LONG Gulf Oil equity ⭐⭐⭐⭐
$760M
profit
#18
Nassim Taleb ACTIVE
Black Swan Profits (2008)

The philosopher-trader who literally wrote the book on Black Swans. His Universa fund bought cheap far-out-of-the-money puts that exploded during the 2008 crash. Returned 115% in October 2008 alone.

🎰 OPTIONS Deep OTM puts ⭐⭐⭐⭐
$500M
profit
#19
Kyle Bass ACTIVE
Subprime Mortgage CDS (2007)

Another Big Short hero. Bass turned $30M into $500M+ by buying credit default swaps on subprime mortgage bonds. His Hayman Capital became famous for macro bets.

📉 SHORT CDS on subprime MBS ⭐⭐⭐⭐
$500M
profit
#20
Carl Icahn ACTIVE
TWA Corporate Raid (1985)

Took over Trans World Airlines in a hostile takeover, sold off its assets, and walked away with $469M while the airline eventually went bankrupt. Defined the era of corporate raiders.

📈 LONG TWA equity ⭐⭐⭐
$469M
profit
#21
George Soros RETIRED
The 1987 Japan Short (1987)

Soros shorted Japanese stocks ahead of the 1987 crash but got caught on the wrong side initially. He then doubled down and made $300M. He said this trade taught him more than any winner.

📉 SHORT Japanese equities ⭐⭐⭐
$300M
profit
#22
Andrew Hall RETIRED
The $100 Oil Bet (2008)

In 2003, when oil was at $30, Hall loaded up on long-dated oil futures betting it would hit $100. By 2008 oil hit $147. Citigroup paid him $100M in a single bonus. Earned the nickname 'God.'

📈 LONG Oil futures ⭐⭐⭐⭐
$250M
profit
#23
Jesse Livermore RETIRED
The 1929 Crash Short (1929)

Shorted the entire stock market before the 1929 crash. Made $100M ($1.5B adjusted) in a single day. Called 'The Boy Plunger.' Later lost it all and tragically took his own life.

📉 SHORT US equities ⭐⭐⭐⭐⭐
$100M
profit
#24
Paul Tudor Jones ACTIVE
Black Monday Prediction (1987)

Predicted and profited from the 1987 crash (Black Monday, -22.6% in one day). His fund returned 125.9% that year while the market imploded. Famous documentary 'Trader' captured it.

📉 SHORT S&P 500 futures ⭐⭐⭐⭐⭐
$100M
profit
#25
Keith Gill (DeepF***ingValue) ACTIVE
GameStop Squeeze (2021)

A Massachusetts financial advisor who posted his $53K GME YOLO on Reddit for over a year. His conviction held through massive drawdowns. Turned it into $46M and became the face of the retail revolution.

📈 LONG GME calls + shares ⭐⭐⭐⭐⭐
$46M
profit

Profit figures are estimates from public sources and may not reflect exact final numbers.

Past performance of legendary traders does not predict future results. This is not financial advice.

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