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4. Jimmy Cayne

Talk about an out-of-touch leader. Cayne was playing bridge when two Bear Stearns hedge funds collapsed in July 2007, and was again the following March when a liquidity crisis at the firm led to its emergency sale to J.P. Morgan. Never mind that its share price was $10 (less than 3 percent of its high of $170); Cayne will spend the rest of his days living down reports that one of his other favorite pursuits was smoking pot.

THE STAT: What a difference a year makes: A share price of $10 doesn’t sound too bad these days.

Bear Stearns Company Website

By Portfolio.com