Estimated Career Earnings: $30,000,000
How He Lost It All: When is $30M not enough money? When you father ten children by eight women. The Bulls forward was arrested in 2007 for failure to make child support payments despite making tens of millions of dollars in his eight-year NBA career. Go hard in the paint, keep it raw in the bed, leave the game penniless; the plight of an NBA benchwarmer.