8. Derrick Coleman

-cash blown: $87 million

This ex-NBA star was drafted during the 1990 NBA Draft by the New Jersey Nets and had a successful career until his exit from the NBA in 2006. At the time of his retirement his total career earnings were just 9 million dollars shy of 100 million US Dollars.

exnba.com

By 2007 he was working as a private developer and entrepreneur in Detroit. His financial investments in real estate got the better of him when he was forced to file for chapter 7 bankruptcy due to a huge chunk of debt of over 2 million dollars among 50 of 100 separate creditors.