Estimated Career Earnings: $60,000,000
How He Lost It All: If you ain't no punk, holler we want prenup—we want prenup! *Yeezy voice* The quickest and easiest way to lose money when you're an athlete is to father children and get divorced, Kenny Anderson did both in a big way. The New York City basketball legend has had three divorces, eight kids, and pays child support to five different women. And he didn't exactly endear himself to anyone when he said of his children, ”They can burn a hole in your pocket real quick... you've got your schooling, day care, nanny. It just goes on and on." We feel you, Kenny. It's hard out here for a pimp.