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Bill Miller
Bill Miller
Legg Mason Capital chairman and CEO

Estimated losses: $198.6 million*

Miller's having a rough ride. One of the country's most celebrated money managers, he beat the market for 15 years straight before hitting a wall in 2006. He's since bet wrong on Countrywide, KB Home and now Bear Stearns. The flagship Legg Mason Value Trust was the bank's second largest mutual fund holder.

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

NEXT: Carl Glickman
Last updated April 03 2008: 8:08 AM ET