Champion: WBC, WBA, and IBF Heavyweight Championship (won first title in 1986)
Offense(s): Rape, road rage, possession of narcotics, DUI
Sentence: Six years, released after serving three
Iron Mike is arguably the most polarizing figure in sports history. The youngest heavyweight champion in boxing history captured the attention of fans everywhere in the mid to late '80s with his vicious knockouts. By the time the '90s rolled around he was becoming just as known for his trouble outside of the ring, none more notable than in 1991 when he was arrested for allegedly raping beauty pageant contestant, Desiree Washington.
Tyson was convicted in February 1992 and served three years of his six-year sentence before resuming his boxing career. Unfortunately when Tyson's boxing career ended in 2005, his criminal career continued with the former champ picking up charges like possession of cocaine and DUI. Thankfully "The Baddest Man on the Planet" has mellowed out and you're more likely to see him on the big screen than behind bars. Being too old for dumb shit FTW.