#7 Lenny Dykstra – A fan favorite in both New York and Philadelphia, Lenny Dykstra was able to win 2 world series during his career. A career in which he missed months of baseball after driving drunk and crashing his car into a tree. Although, that’s small potatoes to his downright sleazy action post baseball including the following allegations and charges: Several counts of sexual assault, grand theft auto, identity theft. possession of cocaine, ecstasy, HGH and indecent exposure. That’s on top of losing a $58 million fortune and getting sentenced to prison for Bankruptcy Fraud.