Estimated Career Earnings: $92,000,000
How He Lost It All: Before you complain about the price of condoms, read the story of Shawn Kemp. It could potentially save you $100,000,000. The Sonics forward fathered (at least) seven children by six women and lost most of his career earnings to child support. His post-NBA life has included a failed comeback attempt, multiple drug possession arrests, and the ultimate athlete rock bottom, playing against a stocky sales rep on Pros vs. Joes. Now that $12 box of Trojan Fire and Ice jimmys doesn't seem like such a burden, does it?