3-time gold medal Olympian, 3-time MVP for the WNBA, first pro women’s basketball player
Estimated lifetime earnings: $50 Million
Swoopes, the “Michael Jordan of the WNBA,” scored her own Nike deal for the Jordan-inspired “Air Swoopes” brand. Swoopes, a marketing machine, enjoyed a stint as the face of the WNBA, but her fortunes didn’t last. She filed for bankruptcy in 2004, citing mismanagement by her agents and layers. She owed nearly $750,000.