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James "Jimmy" Cayne
Bear Stearns chairman of the board and former CEO

Estimated losses: $477.8 million *

Cayne stepped down as Bear Stearns' CEO several months after it was revealed that he was playing bridge and allegedly smoking pot as two of the firm's hedge funds imploded last summer, touching off a crisis in confidence from which Bear Stearns never recovered. Cayne stayed on as the firm's non-executive chairman and is its second-largest shareholder.

*Estimates based on Cayne's holdings at the beginning of 2008, when Bear Stearns stock was trading at $88.35. Cayne sold 25,001 shares on Feb. 14, when Bear Stearns shares were at $80.15 apiece.

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Last updated April 03 2008: 8:08 AM ET