Basketball player Sheryl Swoopes was a three-time Olympic gold medalist and a three-time WNBA Most Valuable Player with the Houston Comets. In 2004 Swoopes filed for Chapter 13 bankruptcy after failing to pay debt she accrued from mismanaged funds, the New York Times reported. Today, Swoopes leads basketball camps and makes motivational speeches. (Kellie Landis/Allsport/Getty Images)