Gold medalist skater; America’s first darling Olympian
Estimated earnings: $1-2 million/year in endorsements
After receiving a gold medal in the 1976 Olympics, Dorothy Hamill became America’s first Olympic darling. After that, her luck turned. A competing skater’s coach tried to run her over. She made a bad purchase in the dying Ice Capades franchise. She survived breast cancer, two divorces, and a gig as a Vioxx spokesperson. A final, failed investment in an Arizona ice skating rink pulled her into bankruptcy.