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Lenny Dykstra

The perpetually tobacco-chewing Lenny “Nails” Dykstra had an illustrious major league baseball career. He was a member of the New York Mets when they emerged victorious from the 1986 World Series, but upon retirement he kept spending money like an active player. Ultimately, it ran out and he filed for bankruptcy. Documents showed he was indebted to both Bank of America and JPMorgan Chase, to such a degree that he was able to claim a staggering $50 million in liabilities.

Dykstra, who was so broke he was forced to sell his World Series ring, put his luxurious Thousand Oaks, Calif., home on the market in 2008 for $25 million. It didn’t sell, and the house wound up on the foreclosure auction block. Dykstra ultimately filed for Chapter 11 bankruptcy protection and in January 2011 the home sold to an unnamed buyer for an undisclosed amount.

Jamie Squire | Getty ImagesInset: Realtor.com