Estimated Career Earnings: $35,000,000
How They Lost It All: Remember when Tiki Barber left football to pursue a lucrative broadcasting career? How'd that work out? The Giants running back awkwardly smiled his way through tiresome cliches on Football Night in America before being banished to the Today Show, where he made Kathie Lee Gifford look like Edward R. Murrow. When he left his pregnant wife for a 23-year-old intern, he was fired by NBC for violating a morality clause in his contract. Kind of makes having your barn rattled by hole-filling linebackers look like an easy way to make a living.

When it comes to athletes, "broke" can be a relative term. While Barber probably isn't missing any meals, he struggled to pay a costly divorce settlement and begged for a contract during last season's lame attempt at a comeback.