Coinage, Life, well spent. Presented by Geico. The greatest pros in sports have earned hundreds of millions of dollars, but not everyone has held onto it. Here are seven athletes who gained a fortune and ultimately found a bit of post career misfortune. Boxing sensation Mike Tyson earned more that $400 million during his career But he ended up filing for bankruptcy in 2003. Maybe this is what happens when you spend money on pet tigers and $2 million bathtubs. Terrell Owens is known for his end zone celebrations but there wasn't much to celebrate after bad investments. A failed Alabama casino, a collapsing housing market, and $50,000 of monthly child support payments all sent him towards bankruptcy All after earning a hefty $80 million. Olympic gold medalist and celebrated figure skater, Dorothy Hamill, made $1 million a year skating in the Ice Capades, but that ice thawed when she later bought the company, which ultimately failed and sent her skating into bankruptcy instead. Another heavy hitter that got knocked out with debt is Evander Holyfield. After a career gross of an incredible $230 million, He lost it all. Paying child support for a reported 11 children has been said to have contributed to his financial woes. Ex-NBA star, Antoine Walker earned more than $108 million through his 13 year NBA career. And reports have said that he financially supported 70 members of his family and friends. But that generosity, along with poor spending and splurging, lead to massive debt and bankruptcy. In 2010. Former New York Jets quarterback Mark Brunell earned an estimated $50 million during his career, but it was bad real estate investments, and business loans that took it all away. He filed bankruptcy in 2010 with about $25 million in debt. Sheryl Swoops was once the shining star of the WNBA banking $50 million during her career as the first female basketball player to ever have her own sneaker. The Nike Air Swoops. Crooked lawyers and agents were said to be the blame for her fall into bankruptcy in 2004, but it certainly looks as though Sheryl wasn't the only pro to fall from that precarious peak of financial success. Coinage, life well spent. Presented by Geico.