Al Capone

Chicago's most famous gangster lost his hold on his empire simply for not paying his taxes.
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Despite all the crimes Al Capone was linked to during his lifetime, from bootlegging to prostitution to murder, the one charge that ever stuck for the notorious Chicago mob boss was tax evasion. The biggest name of the Prohibition Era was out behind bars for not paying his taxes.

In 1931, Capone was sentenced to 11 years for not paying $215,000 plus interest in taxes. Capone didn't serve out the full sentence, but sending him away to jail dissolved Capone's ties to organized crime.

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