21. Lawrence Philips
A successful running back in the NFL and CFL, Philips first came to prominence when he was a two-time national college football champion with the Nebraska Cornhuskers. He’d go on to play for the Miami Dolphins and San Franciso 49ers. So far so good, but he definitely wasn’t a nice person.
In the early 2000s, he was convicted multiple times for battery and domestic violence, eventually running up a sentence of 31 years in prison. That’s not all though. He’d also be found guilty of the murder of his cellmate Damion Soward. Philips would commit suicide in his cell as the death penalty was being considered. A crazy story.