12. Sheryl Swoopes
Source: Iconosquare
The lovely Sheryl Swoopes filed bankruptcy in 2004. The greatest WNBA player in history has medals and awards to show for her greatness, but no money. She had money too until she made one of the worst mistakes a wealthy person can make. With $50 million dollars from an unbelievable Nike deal, 2004 was when Sheryl hit rock bottom. Why? Swoopes trusted her millions with the wrong people and it left her with nothing.