Derrick Coleman Made $91,000,000
The bankruptcy of this troubled superstar-that-never-was is actually a bit sad when compared to the other players on this list. Coleman, who earned more than $91 during his 15 year NBA career, invested a large portion of his money in an effort to revitalize the city of Detroit. Through real estate and other business ventures (ownership stakes in a Hilton Hotel, a pizza and doughnut franchise) Coleman hoped to rejuvenate his hometown.
Unfortunately, real estate investments — especially in areas hit hardest by the economic crash of the last decade — always seems to be the harbinger of bankruptcy, especially for pro athletes. Coleman filed for Chapter 7 bankruptcy in 2010, owing over $2 million to as many as 99 different creditors. He has since sold his remaining assets to pay off those creditors.