Estimated Career Earnings: $60,000,000
How They Lost It All: In a bizarre role reversal, the "QB-Killa" has been murdered in the wallet and is now, apparently, dead broke. Sapp has accumulated $7M worth of debt and is suffering from the definitive athletic income hemorrhage: four baby mamas. Having "lost" his championship rings (one Superbowl, one National Championship), Sapp claims a lion skin rug, Muhammad Ali autograph, and some 240 pairs of Jordan brand sneakers as assets—not exactly dividend yielding investments.