MIKE TYSON – $10 MILLION

Mike Tyson was once the undefeated boxing champion of the world back in the 1980s. He was a good fighter who stood his ground against his enemies, though there were times when he faced a bit of controversy. Sadly, the money he earned from his winnings as a professional boxer was managed poorly. In 2003, Tyson has already declared bankruptcy.

He was considered to be the hardest hitter in heavyweight history by ESPN, which speaks volumes about his skills in the boxing ring. Although he went through some ups and downs in his career, he defeated his opponents with ease during his comebacks, though he wasn’t able to hold on to his career that much long. He has since earned money by making personal appearances at various events. He also took on some acting roles, with one of his most popular appearances being in The Hangover.