3. Riddick Bowe
Record: 43-1-0 (33 KOs)
Former Undisputed Heavyweight Champion
Estimated Career Earnings: $50 million
With only one loss on his professional record, Bowe holds the distinction of being the only boxer to defeat Evander Holyfield twice. After becoming the undisputed heavyweight champion of the world at the age of 24, Bowe brought in millions through fight purses and endorsements from companies such as FILA. So, how did the former champ go from making millions to trying to sell his own autographed memorabilia at a flea market in New Jersey? Bowe admits to splurging on lavish homes, luxury cars and helping out friends and family but also says his money was mismanaged by advisers. Kind of ironic considering his boxing nickname was Sugar Man.
