10 Surprising Bankrupt Athletes

Gaylord Perry
Gaylord Perry signs autographs during the 1995 All Star Weekend in Arlington, Texas. Sporting News via Getty Images

Hall of Fame MLB pitcher Gaylord Perry is as famous for his on-the-mound antics as his remarkable 314 wins and 3,534 strikeouts in the 1970s and 1980s. During his long and storied career, Perry's name became synonymous with the "spitball," an illegal pitch doctored with spit, Vaseline or hair tonic that starts fast, then drops like a rock [source: Armour]. Perry admitted the crime in a 1974 memoir, but was never officially sanctioned — rumor has it that dozens of other pitchers were equally "greased."

While still playing, Perry bought 400 acres (161 hectares) of land in rural North Carolina as a retirement plan. Perry grew up on a farm nearby, plowing fields at age 7 to help his sharecropper parents raise tobacco, corn and peanuts [source: Armour]. After pitching for 22 years in the majors, Perry's dream was to ride his tractor into the sunset. Unfortunately, the economics of family farming were against him, and he was forced to declare bankruptcy and hand the farm over to the bank in 1986 [source: Mayo].