Mike Tyson

Mike Tyson's 1986 knockout of Trevor Berbick made him the youngest heavyweight champion at 20 years old — a record that still stands — yet his legacy is overshadowed by the 1997 ear-biting incident that cost him a $3 million fine and a temporary ban. His 1992 rape conviction led to three years in prison, but he later rebuilt his image with a one-man show grossing $1.5 million per night. Tyson's controversy surpasses #6 Serena Williams in sheer criminality, though his later redemption arc outshines #8 Floyd Mayweather Jr.'s legal troubles.