Sport: Boxing
Criminal History: Murder
Time Behind Bars: 10+ years

Esteban De Jesus held the WBC lightweight championship belt for almost two years. Like many on this list, he started dabbling with drugs and his life took a turn. On Thanksgiving weekend of 1981 De Jesus found himself in a heated traffic dispute with a 17-year-old man. De Jesus shot the teenager in the street.  

While in prison, De Jesus became a born-again Christian preacher and was pardoned by a Puerto Rican Governor when it became public knowledge that he was suffering from AIDS. The embattled boxer died of the disease in 1989.