4. Lenny Dykstra
After his playing career was over, the former Mets and Phillies hero became an unlikely star on Wall Street, managing a stock portfolio, and even writing a column for Jim Cramer’s website. In 2008, he started a magazine for former players called Player’s Club and a high-end jet charter company. In 2006, he claimed his net worth was around $50 million. By 2009, he was living out of his car. After a 2009 article in GQ exposed his business as a disorganized mess, the cards began tumbling. He filed for bankruptcy in 2009, both of his homes were foreclosed on, and a number of women accused him of sexual assault. He was arrested for grand theft auto, cocaine possession and identity theft. He was forced to sell his World Series ring, and he appeared in Federal bankruptcy court earlier this year, charged with embezzlement, obstruction of justice and bankruptcy fraud. He could spend the rest of his life in prison. —Johnny Goodtimes
(AP Photo/Nick Ut)
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