A handful of trades are so large and so right that they became legend — repricing currencies, breaking central banks, and minting the fortunes hedge fund history is written around. These are the ten greatest, with the actual numbers.
The Hall of Fame
Profits are approximate, per the most-cited public accounts:
| # | Trader | Trade | Year | Profit |
|---|---|---|---|---|
| 1 | John Paulson | Shorting subprime CDOs | 2007 | $15B (fund), $4B personal |
| 2 | George Soros | Shorting the British pound | 1992 | $1B+ in a day |
| 3 | Stanley Druckenmiller | Long Deutsche mark after Berlin Wall | 1989-90 | $1B+ |
| 4 | Michael Burry | CDS against subprime (The Big Short) | 2007-08 | $800M (fund) |
| 5 | David Tepper | Buying bank debt at the 2009 bottom | 2009 | $7B (fund), $4B personal |
| 6 | Paul Tudor Jones | Shorting Black Monday | 1987 | $100M, +125% month |
| 7 | Andy Krieger | Shorting the NZ dollar | 1987 | $300M for Bankers Trust |
| 8 | Jesse Livermore | Shorting the 1929 crash | 1929 | $100M (~$1.8B today) |
| 9 | Kyle Bass | Subprime CDS | 2007 | $500M+ (fund) |
| 10 | Bill Ackman | CDS hedge into COVID crash | 2020 | $2.6B on $27M premium |
What the Legends Share
Asymmetry over frequency: every trade here risked a small, defined amount against a massive payoff — Ackman's COVID hedge turned $27M of premium into $2.6B, a 96:1 return. None were all-in gambles; all were sized so being wrong was survivable. That's Kelly thinking at civilization scale.
Being early is indistinguishable from being wrong — until it isn't: Burry endured investor revolts for two years before subprime cracked. The uncomfortable lesson: legendary trades required both the analysis and the stomach to hold through sustained pain.
The survivorship warning belongs here too: for every Soros there are thousands of blown-up currency shorts nobody writes articles about. Study the risk management, not the glory.
Frequently Asked Questions
What is the greatest trade ever?
By most accounts John Paulson's 2007 subprime short — roughly $15B in fund profits, the largest single-strategy windfall in market history.
Did Soros really 'break the Bank of England'?
His Quantum Fund's massive short forced sterling out of the ERM on Black Wednesday 1992, clearing over $1B — the trade that made the phrase.