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Jesse Livermore

Position: Trader
Claim To Fame: Shorted Crash of 1929

Nicknamed "Boy Plunger" Jesse Livermore is among the very few investors who profited handsomely from both the Panic of 1907 and the Great Crash of 1929 largely due to short positions that generated as much as $100 million.

His philosophy of trading is still widely citied, 'increase the size of your position if they're moving in your favor and cut losses quickly.' Livermore died in 1940 at the age of 67.

Photo Credit: New York Daily News Archive