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Al Capone controlled most of Chicago's speakaesies, bookie joints, brothels, horse and race tracks, gambling houses, and distilleries.  It was reported that he earned close to $100 million every year just from his illegal businessess alone (today that would be roughly $1.2 billion).  

Al Capone was generally very careful about making sure that all of his business deals were done with cash or a third party.  However, he was not able to run from the government forever.  On October 17th, 1931, Capone was found guilty of 5 out of 22 tax evasion charges.  He was sentenced to 11 years in prison as well as forced to pay large court fees.  

Al Capone was thought to have personally killed dozens of people and ordered the deaths of hundreds more.  

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