31. Jayson Williams
Criminal History: Aggravated assault, covering up a crime
Time Behind Bars: Two years
After an injury ended his NBA career, Jayson Williams' life went into a tailspin. He was charged with DWI for crashing his car into what has to be the only tree in Manhattan and punched a man in the face outside of what has to be the only nightclub in North Carolina. Then, Williams continued his "active retirement" by giving one hell of a tour of his house. The former Nets center was showing off his palatial estate and toying with a shotgun when it went off, blasting a hole in his chauffeur's chest and ultimately killing the driver. He was eventually acquitted of manslaughter, but was sentenced to five years in prison for covering up the shooting in 2010.