Estimated Career Earnings: $100,000,000
How He Lost It All: When Reebok retros the Pumps, does Vin Baker get any of that cash? We hope so, he needs it. The four time All-Star went from the poor man's David Robinson to—well, just plain poor through years of gambling, alcoholism, and bad investments. Baker lost his restaurant (the cleverly named Vinnie's Saybrook Fish House) and his 10,000 square-foot Connecticut home in 2008 to foreclosure.