Lenny Dykstra (Bankrupt in 2009): Baseball star and (absurdly) investment guru Dykstra recently filed for Chapter 11 thanks to an ill-advised business venture — a glossy magazine for millionaire athletes called The Players Club. Not only was Chapter 11 necessary, but the business resulted in 20 lawsuits. (Read more on this in an older column about investment failures of the stars.) Most recently, he was convicted of bankruptcy fraud — facing up to 20 years in prison for hiding sports memorabilia and other items from liquidators and then selling it after the fact. The icing on the cake? He previously pleaded no contest to grand theft auto and exposing himself to women he met through classifieds site Craigslist.
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