3. Dorothy Hamil
Source: Iconosquare
Like many Olympic stars, Dorothy Hamil landed in the poorhouse, despite her best efforts. In 1976, Hamil won an Olympic gold medal and landed a shampoo endorsement. Although she was the main attraction of the Ice Capades, it wasn’t enough to keep her riches flowing. Interest in the event didn’t flourish like she had hoped after purchasing the Ice Capades, so she sold the company and filed for bankruptcy in 1995.