Estimated Career Earnings: $200,000,000
How He Lost It All: Allen Iverson is as reckless and brave with his checkbook as he was on the basketball court, and now, he's paying the price (literally). The Answer has apparently blown nearly a quarter of a billion dollars on jewelry, jets, and an army of enablers—suddenly that contract offer to play indoor soccer for the Rochester Lancers doesn't seem like such a bad idea. Unfortunately for A.I., diamond-encrusted Cartier watches don't appreciate like bonds, if they did, the Sixers guard would be Warren Buffett.