Estimated Career Earnings: $110,000,000
How He Lost It All: What's crazier—that Antoine Walker somehow made over $100 million in his NBA career or that he managed to blow it all within three years of his retirement? The man-boobed former Celtic lost his cash, like many on this list, by supporting an enormous entourage. According to his mother (who lives in a mansion outside of Chicago with 10 bedrooms and a full-sized basketball court), Walker supported as many as 70 people during his playing days and turned his garage into a parking lot of luxury cars. From bad to sad, Walker was arrested in 2009 for passing bad checks to a Vegas casino totaling a million dollars. He most recently got waived by the D-League's Idaho Stampede. We're not even going to make anymore jokes about this dude. His story is just too sad at this point.