16. Michael Vick

Michael Vick is best known for his illegal dog fighting scandal. He was charged and jailed in 2007. But his troubles with money started before that. In 2006 he was earning $25.4million annually. However, poor financial management and bad investments crippled his finances. Almost certainly lawsuits always follow financial troubles. Vick suffered from an incinerating lawsuit with his sports agents.

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When he was jailed for dog fighting, things got from bad to worse. Vick filed for bankruptcy in 2008. He was more than $50million in debt. At that time he was working in prison as a janitor at 12 cents per hour. Admirably he covered and went on to play football again once he got out of jail. He seems to be doing fine now but his glory days are well behind him.