Floyd Mayweather, Sr.

Record and Accolades: 28-6-1 (18 KOs); Former UBF champion
Year: 1993
Crime: Drug Trafficking
Sentence / Time Served: 5 years / 3 years
Floyd Mayweather, Sr. went to jail on some interesting terms. From 1987 to 1992, he and a couple colleagues were smuggling cocaine into the United States in detergent boxes. In 1993, he was eventually caught, charged with drug trafficking, and served three of the five years in jail. Boxing x jail bids? Like father, like son.