25. Ryan Leaf, San Diego Chargers:
Leaf is a rare breed of player. He’s largely known for being the clear-cut top choice on the list of biggest NFL draft busts of all-time. But his post-football life after failing as the San Diego Chargers’ starting quarterback was much worse.
Leaf was hired as a volunteer quarterbacks coach at West Texas A&M in 2006. Two years later he was put on indefinite leave and then resigned the next day for supposedly asking one of his players for a painkiller to help him deal with a prior injury from his career. Leaf’s opioid use began in 2002. He acquired Vicodin at a boxing match, which “started about an eight-year run of off-and-on opioid abuse that took my life to the very bottom.” Indeed it did.
Leaf was arrested on burglary and controlled substance charges in Texas in 2009. In 2012, he was caught again on theft, burglary, and drug charges in his Montana hometown. He was sentenced to seven years in Montana prison and eventually released in December 2014. He has been sober for six years and now serves as a Program Ambassador for Transcend Recovery Community, but he’s still one of the most notorious criminals in football history.