Estimated Career Earnings: $50,000,000
How She Lost It All: Who says the WNBA players don't make serious dough? Sheryl Swoopes made almost $50M dollars as the league's poster child only to lose it all with horrible representation and bad investments. The first woman to get her own Nike shoe blamed herself for the epic mismanagement of cash and sold her Olympic medals and Naismith trophy to satisfy the milli she owed creditors (including $250,000 to the IRS).