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The greatest trades in market history — Soros breaking the Bank of England, Burry's big short, Druckenmiller, Paulson and more, with the numbers behind each.
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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.
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 |
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.
By most accounts John Paulson's 2007 subprime short — roughly $15B in fund profits, the largest single-strategy windfall in market history.
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.