Jason Williams Made $63,000,000
A late-bloomer who made his only All-Star Game at 30 and had his career end due to injury at 31, Jayson Williams could very well have been the next Charles Barkley as a TV analyst. He did work for NBC for a while but lost his job in 2002 after accidentally discharching his firearm and hitting his limo driver.
While it wouldn’t be until 2010 that he served his 27-month prison sentence for the fatal shooting, Williams had a string of problems before then, including multiple other legal issues, substance abuse addictions, and going broke.
Despite his personal problems, Williams always was a generous guy and was known around New York for his $500 tips. All of that added up and contributed to his defense lawyer revealing that Williams was nearly bankrupt during his 2010 court case, despite making over $63 million.
After being released from prison in 2012, Williams turned his life around and now operates the Rebound Institute, a recovery and wellness center in South Florida.