Al Capone murdered, stole, bribed and bootlegged, but as far as the federal government was concerned, failing to pay taxes really made Capone a criminal. The thing is, the IRS has a massive Catch-22 up its sleeve — just because your income is illegal doesn’t mean you don’t owe taxes on it. After over a decade of terrorizing the city of Chicago, Capone was convicted of tax evasion and sentenced to 11 years in prison.
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