International Business Times has a list of some of the “Greatest Trades Ever”

It is rather incomplete, says Barry Ritholtz at The Big Picture,  leaving out Felix Zulauf’s Japan short in 1989, any Bullish trade in 1982, numerous stock specific trades (Long Apple, Short Enron, etc.), the many trades against the Dot Com bubble, in favor of Treasuries (1982-2010).

Regardless, it is an interesting conversation starter:

International Business Times – Top 10 greatest trades of all time

1. John Paulson’s bet against subprime mortgages

2. Jesse Livermore’s call on the Crash of 1929

3. John Templeton’s foray into Japan

4. George Soros’ breaking of BOE

5. Paul Tudor Jones’ shorting of Black Monday

6. Andrew Hall’s $100 oil prediction

7. David Tepper’s 2009 bet on financials

8. Jim Chanos’ prescient shorts

9. Jim Rogers’ early call on commodities

10. Louis Bacon’s geopolitical play

Note the bias towards big macro calls . . .

<i> From Top 10 greatest trades of all time (?) by Barry Ritholdz at The Big Picture – 7 January 2011 </i>