4. Al Capone
This has become such a well-known name in the country (and perhaps the world), that even movies were based off of him. Al Capone had a worth of over $1 billion and made history (in the United States) for being the most ruthless gangster.
He became involved in the drug industry at a young age and it stuck with him for most of his life. During the prohibition, he relocated to Chicago from New York to act as a bodyguard for those who were smuggling alcohol. During these times, technology was not as advanced as it is today and gathering evidence was no easy task.
Authorities eventually arrested him, not for alcohol smuggling, but for tax evasion. He did serve time in prison, but only served eight years out of the original 11-year sentence. Just a few years after being put back into society, Capone died after suffering from a cardiac arrest.
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