1. Mike Tyson

Record and Accolades : 50-6-0 (44 KOs); Former Undisputed Heavyweight Champion
Estimated Career Earnings: $350-400 million
Iron Mike was not only the top earning boxer of his time, but one of the highest paid athletes period. In 1991, he came in second on Forbes' top earning athletes list--beating out competition like MJ--with an estimated $31.5 million earned. He had major endorsement deals with companies like Pepsi, his own video game, and brought in unprecedented purses from his championship bouts. Or at least we thought he did. According to Tyson, promoter Don King robbed him of $100 million. Tyson sued the promoter in 2003 but ended up settling out of court for $14 million. Think Tyson is still bitter about losing that cake to King, today? Uhh...is calling someone a "wretched, slimy, reptilian motherfucker," a strong enough statement for you?