5. Dennis Rodman – $-1 million
Aside from a very brief stint as Madonna‘s boyfriend, Dennis Rodman is known for being a professional NBA player (at 54, he’s long retired). He was quite successful at it, earning $29 million in contract salary alone, notwithstanding the extra money he made from endorsements and sponsorships. So when, in 2012, he went to court to face charges that he owed his ex-wife $800,000 in child support, it should’ve been a breeze to pay it off, right? Wrong. His lawyers claimed that the former ball player was completely broke due to living lavish and couldn’t afford a dime of the payments he had to make. So much for girls dating NBA players for their money!
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