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The winner of the first season of the American show “Survivor”, Richard Hatch, served 4 years in prison for tax evasion after failing to report his winnings to the IRS.
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Shakespeare became wealthy by hoarding grain, and reselling at inflated prices during a period of famine. He used the profits for money-lending activity and was pursued by authorities for tax evasion and was prosecuted for hoarding grain.
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In the 1900s Argentina had a tax on unmarried men that included an exemption for single men who had proposed to a woman for marriage but were rejected. Women then started proposals rejection businesses where they would charge to turn down proposals from bachelors seeking to evade the tax.