Lenny Dykstra
In 2010, three-time MLB all star and World Series Champion Lenny Dykstra was so far in debt he was forced to auction off his World Series ring. Lenny started “Player’s Club,” a high-end jet charter and luxury magazine that went belly up. He went on to purchase Wayne Gretzky’s home for $17.5 Million, which was highly overvalued and the downward spiral was on. Lenny was beyond broke and turned to a life of crime. In 2012, Lenny was convicted of fraud on top of pleading no contest to exposing himself to women he met on Craigslist. Classy.