Ryan Leaf
Leaf was quarterback for four seasons for the San Diego Chargers and the Dallas Cowboys between 1998 and 2001, and also spent time with the Tampa Bay Buccaneers and the Seattle Seahawks. He picked as second overall in the 1998 NFL Draft after Peyton Manning. However his career was short as it was always filled with poor play, bad behavior, and injuries. Leaf really struggled with his work ethic and his ability to stay focused. In fact, an episode of NFL Top 10 ranked him as the No. 1 “draft bust” in NFL history. After he retired, he’s been in and out of prison, penniless.
Eric Naposki
Oh, you forgot about Naposki? That’s okay, he only played two seasons with the New England Patriots, one season with the Indianapolis Colts, and four seasons with the Barcelona Dragons, with who he did win World Bowl V in his last season. He could have had a decent career if he wasn’t a convicted murderer serving life in prison without parole. He was charged with the killing of Bill McLaughlin so that McLaughlin’s girlfriend, Nanette Johnston, could collect on his life insurance. Naposki was romantically involved with Johnston at the time. His money from his brief stint in the NFL is long gone.