Al Capone

Famous American gangster Al Capone, shown here in 1930, lived from 1899 to 1947.

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Did you think that Native American reservations and the embassies of foreign countries were the only non-U.S. territories in mainland United States? Think again. From his ascension to mob boss in 1925 until his conviction for tax evasion in 1931, Al Capone ran the Chicago suburb of Cicero as his own private kingdom. And Capone ruled the kingdom with one personal commandment: plausible deniability in the eyes of the law. For example, when mob associates posed as cops and machine-gunned seven members of a competing gang in what became known as the Valentine's Day Massacre, Capone was (conveniently) in Florida.

Though he got nailed a couple times for rinky-dink charges like contempt of court and possession of a concealed weapon (he once famously said, "You can get much further with a kind word and a gun than you can with a kind word alone."), it was the taxman that finally brought down the mighty Capone. Though he paid taxes on only a paltry legit yearly income, he lived like the king he was.

Where did the money come from and why hadn't he paid taxes on it?

When the federal government asked this question, it landed Capone in the slammer for 11 years, of which he served seven and a half. Though only 40 years old at the time of his release, Capone's brain was riddled with syphilis and he never returned to Chicago.