Dennis Rodman
The eccentric former NBA star is perhaps most notorious for his friendship with North Korea’s dictator, Kim Jong-un, but he’s also gotten into financial trouble with Uncle Sam. Rodman not only owed the IRS $350,000 in back taxes in 2012, he also failed to pay both spousal and child support. Some of his money problems probably can be chalked up to lavish spending, like his Ford 350 pickup with a self-portrait on the hood and a 47-foot speedboat that he named Sexual Chocolate.
