14. Andre Rison
Andre “Bad Moon” Rison managed to sign an incredible $17 million dollar contract with the Cleveland Browns back in the day. There he was a prominent and successful wide receiver and earned even more money from various revenue streams.
However, like many other players on the list, things got difficult for Rison outside of football. After he retired he spent large sums of his money and in 2007 he was ordered to file for bankruptcy after failing to pay for child support.
