Richard Hatch
Money owed: $600,000
Prison sentence: 4 years
5 of 10
Fifty-two million people watched Hatch take home the Survivor’s first million-dollar prize, so it only makes sense that the IRS knew about it. In January of 2006 Hatch was convicted of failing to list his winnings on his tax return and was sentenced to jail and home confinement for more than three years. Yet Hatch, now on Celebrity Apprentice, was again busted in 2010 for … failing to file his taxes. Sentenced to nine months, he began serving his time this month.
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