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Bruce Sherman
Bruce Sherman
CEO of Private Capital Management

Estimated losses: $478.5 million*

The activist investor was selling Bear stock and had been critical of the bank's myriad problems. But Private Capital Management, which is also a division of Legg Mason, didn't sell fast enough: The firm still had 5.5 million shares at the start of the year.

*Estimates based on Private Capital Management's holdings at the beginning of 2008, when the stock was trading at $88.35.

NEXT: Bill Miller
Last updated April 03 2008: 8:08 AM ET