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