21 cases. Two centuries. No crystal ball.
Legendary
trades.
The thesis.
The nerve. The numbers.
Before they became market folklore, they were uncertain decisions. Explore the bets, the people who made them, and the cost of waiting to be right.
Start with the stories ↘A great trade starts
with a different question.
How long can a government defend its currency? What is actually inside that mortgage bond? What happens when everybody’s risk model tells them to sell at once?
The profit is the part we remember. The interesting work happens before it: finding a contradiction, choosing how to express it, and surviving the period when the market disagrees.
This collection brings the stories and their models together. Read for the decision. Stay for the details.
George Soros / 1992
The day a promise broke.
George Soros, sterling, and the limits of a central bank’s resolve.
Read the case ↗Michael Burry / 2007
The answer was in the loans.
Michael Burry and the work hidden beneath a reassuring label.
Read the case ↗Bill Ackman / 2020
Insurance before the alarm.
Bill Ackman and the cost of protection before panic.
Read the case ↗Different decades.
Different kinds of conviction.
Each point is a case, positioned by year and the model’s estimated dollar profit. Explore a point to read the story. The vertical scale is logarithmic so smaller estimates remain visible.
Source estimates, not a performance ranking. Waterloo and Medallion are excluded; points sharing a year may be slightly offset for legibility. Nominal dollars across eras are not purchasing-power equivalents.
Find your next rabbit hole.
Dollar figures are source estimates in nominal USD, except Ackman’s proceeds-to-profit correction. They are not audited or directly comparable. Open a case for its qualifications.
* Medallion’s 1988 year is a source timeline marker, not the period of the illustrative profit model. The Waterloo case is retained as disputed history.
The part worth keeping.
An edge needs a mechanism.
A weak currency, a fragile mortgage or an overpriced business is only the beginning. What instrument translates that insight into a payoff?
Being early has a price.
Premiums, financing, margin and impatient investors all run on a clock. The ability to wait belongs inside the thesis.
The denominator changes the story.
Profit divided by premium tells a different story from profit divided by notional exposure. A fund’s annual return is a third number.
Survival rarely makes the headline.
This is a collection of selected winners. It cannot tell you the odds of winning, the size of unseen losses or whether an approach is repeatable.
Keep the story.
Check the numbers.
The starting point
Based on the 21-case Legendary Trades Models workbook supplied for this collection: Master Comparison, Trade P&L Models, Category Analysis, Common Patterns and Timeline. The source contains estimates without trade-level documentary citations. The original file remains private.
Each case identifies its source row. Selected primary sources support historical context; they do not verify every position, profit, duration or fund-return estimate. Editorial lessons are interpretations.
The limits of the comparison
Positions may mean notional exposure, cash invested or premium paid. Profits may cover different periods. We therefore avoid aggregate profit totals, average returns and a “best trader” ranking.
Ackman’s proceeds are adjusted for the stated premium and commissions. Waterloo is marked disputed. Medallion is a strategy illustration. Models omit many real-world costs and are educational, not investment recommendations.