Mike Tyson was arguably the most feared boxers in the 1990s, winning his first 19 matches with knockouts. After spending time in jail for sexual assault in the mid-90s and the 1997 Holyfield incident with the ear, Tyson never re-developed his skill and soon ended up retiring from boxing. Through the years of his successful career, Tyson earned around $400 million, but he ended up blowing his fortune by 2003. Tyson had spent all of his money on unnecessary luxuries like multiple mansions, luxury cars, and even pet tigers. Tyson had ultimately filed bankruptcy for over $27 million in debt.