#1
Evander Holyfield was one of the great boxing stars of the 1990s and amassed more than a quarter of a billion dollars in purses during his illustrious career. Apparently, though, $250 million doesn't go as far as it used to.

Holyfield, who filed bankruptcy in Fayette County, Ga., in 2008, reportedly owes in excess of $372,000 in child support and may wind up in jail if he does not resolve the issue, according to a TMZ report.