Estimated Career Earnings: $50,000,000
How He Lost It All: Is it too late for Dennis Rodman to make a comeback? The Worm is broke and, according to his attorney, can't pay the nearly $1 million he owes in back child support. We can only guess how Rodman blew his cash, but we're willing to bet it's lost in empty bottles of Wild Turkey and gold plated naval piercings. He's reportedly made $8,000 in the past year, and at that pace, will need over a century to pay what he allegedly owes in alimony.