Estimated Career Earnings: $91,000,000
How He Lost It All: When you make close to $100 million in your career go ahead and buy some jewelry, fur coats, and Bentley GT's—you deserve it. But, for the love of Isiah, don't take it upon yourself to stimulate Detroit's struggling economy. Coleman, who ended his career with the Pistons, lost a fortune attempting to create jobs and revitalize business opportunities in Motown during 2009 and 2010. Before labeling the Michigan native a martyr, it's important to note that Coleman's assets included two chinchilla coats (because it's cold in Detroit), 40 Rolex watches (bosses got to be on time), and a 1970 Chevy Nova (uh, what?).