Estimated Career Earnings: $7,000,000
How He Lost It All: The Detroit Pistons Bad Boy won a championship in 1990, but had to hawk his ring while filing for bankruptcy in 2010. At the time of his filing, Mahorn had less than $2,000 to his name. Despite earning millions in the NBA, signing a lucrative broadcasting deal with the Pistons, and his stint as a coach in the WNBA in 2009, the former NBA forward lost everything. Mahorn's property investments crashed along with Detroit's economy, leaving him with over $500,000 in liabilities and less than $300,000 in assets. Now, we're not very good at math but we're pretty sure that's bad. Mahorn also owed a local library some $55 in late fees. Rick, we know you and Bill Laimbeer had every intention of ripping through the Hunger Games trilogy, but bring your books back homie.