7. Jason Caffey – $34 Million Lost


Caffey had 10 children from 8 different women, he filed for bankruptcy after being arrested in 2007 for failing to pay child support.

8. Dennis Rodman – $27 Million Lost


Rodman filed for bankruptcy claiming he had nothing to get out of back owing child support payments. Probably explains his new friendship with Kim Jong-Il, he’ll do anything for some cash.