Estimated Career Earnings: $20,000,000
How They Lost It All: When you're an athlete, the easiest way to bleed cash is by fathering children and developing a drug habit. We don't care what Barrett Strong says, the best things in life are expensive and kids can be pretty pricey too.

Travis Henry fathered a rather impressive 11 children by, an even more impressive, 10 women. The one-man fertility clinic racked up an annual child support bill of almost $200K and was jailed for falling $16K behind on one of his seeds in Florida. With the pressures of bankrolling his obliviousness to condoms, Henry made the natural transition from NFL running back to drug kingpin. In 2009, he was convicted to three years in federal prison for funding a narcotics ring that ran cocaine between Colorado and Montana.