Estimated Career Earnings: $100,000,000
How He Lost It All: Latrell Sprewell once famously turned down a 3-year, $21 million dollar contract offer by saying, "I have to feed my family." But because he was unwilling to negotiate at the farmers market or wait in line at Costco, the $100 million he made over his career wasn't enough to keep food on the table. Sprewell blew everything on a lavish lifestyle, yachts, and recently had his second million dollar home foreclosed upon. How does a guy who once made $21 million in a season have mortgage payments? The NBA, where amazing happens.