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Mike Tyson earned a reported $400 million over his career but he was knocked down with a $23 million debt in 2003.
The heavyweight champion declared bankruptcy, returned to jail, and went through rehab before he again reached financial stability.
By 2003, he owed money to the IRS, British tax authorities, lawyers, a personal trainer, a financial manager, and a music producer, among others. Tyson had to pay $9 million in a divorce settlement and was also behind on child support.
Today, Tyson has retired from fighting and appears to be solvent again. In 2018, Tyson started a marijuana company in California called The Ranch Companies. This year he revealed he wants to start a cannabis-themed resort.