Lenny Dykstra, New York Mets – Legal Fees and Debt

Former baseball player Lenny Dykstra is best known for his years with the Mets, from 1985 to 1989. Dykstra, unlike many other athletes, not only ended up broke but also went to prison. Believe it or not, after his baseball career ended, the former MLB star spent three years in a state prison for grand theft auto.

To make matters even worse, Dykstra filed for bankruptcy back in 2009, more than a decade after his release. Reportedly, he owned $31 million in debt, in contrast to the $50,000 he had in the bank. As a result, Dykstra had to auction thousands of possessions, including his $18.5 million mansion that he brought from professional hockey player, Wayne Gretzky.