10. Jason Caffey ($30,000,000)
Bad choices can ruin a player’s life and a fool and his money are soon parted- this guy proves two sayings with a single attempt! He started to father 10 children through the 8 women he has been with. Now that has to burn a lot of money (and divorce settlements can take a large chunk of what you own). In fact, he was so poor at the end, that he was arrested for being unable to pay any child support payments to his ex wives! The Bulls forward was arrested in 2007 for this purpose and comes at the 10th spot in our countdown.