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Michael Jackson
Despite a contract worth nearly $1 billion in his career, Michael Jackson filed for bankruptcy in 2007.
In 2005, a child abuse lawsuit and trial revealed that Jackson had been spending $20 to $30 million more a year than he was actually earning. He even nearly lost his famous Neverland Ranch after he took out a $25 million loan on the house and couldn't pay it off. Foreclosure proceedings started but his celebrity status prevented the loss of the home. It's rumored that his remaining debt could be as high as $500 million.






















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