4) Brad Friedel (American)

This 43-year-old shiny-headed goalkeeper declared bankruptcy in January 2011 when a football academy he started in his hometown Ohio, ran up debts. The not-for-profit venture was set up to help youngsters in the US to adapt better to European football. SEE ALSO: The 10 most ridiculous storylines in WWE history – #1 will leave you in a big shock! (With Pictures)

He did not make any money on it whatsoever. Fortunately he still has some years left in him to earn some cash back.