5. Thomas Hearns
Record: 61-5-1 (48 KOs)
Held eight world titles in six different divisions
Estimated Career Earnings: $40 million
Thomas Hearns became the first boxer to hold five titles in five different divisions. But last year, the Hitman’s biggest blow came when he was forced to auction off most of his prized possessions in order to pay tax debts of $250,000. Hearns says he lost most of his fortune by helping out members of his large family, a decision he says he does not regret making.