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7. Fred Joseph

As Michael Milken’s boss, Joseph led Drexel to “it” firm status on Wall Street in the 1980s. He then oversaw its plunge into bankruptcy in 1990, after company executives were convicted of insider trading and forced to pay $650 million in fines. There was no evidence that Joseph himself committed a crime, but his poor management left the company without a crisis plan. In 1992, Drexel defaulted on $100 million in loans and closed up shop. Unlike Milken, Joseph didn’t go to jail, but he was banished from being a Wall Street CEO for life.

THE STAT: Joseph has since become managing director of Morgan Joseph & Co. In 2007, an industry group named him investment banker of the year.

By Portfolio.com