Estimated Career Earnings: $40,000,000
How They Lost It All: If you want to be a millionaire, all you have to do is wrist-snap a couple 70-yard bombs in the Sugar Bowl and the Oakland Raiders will undoubtedly ink you up on a ridiculous contract. The Silver and Black learned an important lesson about the eye test when they picked the LSU quarterback first overall in the '07 draft, and JaMarcus Russell learned how easy it is to spend and purple drank your way through a fortune.

Although he claims he's "far from" broke, Russell fell behind on the mortgage payments for his Oakland mansion and had to pay a lien to the state of California for over $200K in back taxes. How a dude who once made $17M in a season even has a $2M mortgage is lost on us, but professional athletes spend with the discipline and restraint of a tumescent Charlie Sheen on a bender. A comeback is going to be hard for the historic bust who showed up for a recent tryout with the Redskins weighing almost 300-pounds.