Al Capone is perhaps the most notorious gangster in American history. However, on October 17th, 1931, he was convicted and later sentenced to 11 years in prison. The FBI had attempted to imprison Capone for years, but it wasn’t his crimes of murder, blackmailing, or bootlegging that finally put him away. Rather, the infamous gangster was convicted of the dastardly crime of tax evasion. 

Born on January 17th, 1899, Al Capone would rise to prominence during the 1920s. His gang controlled the South Side of Chicago and made incredulous amounts of money by bootlegging alcohol (during Capone’s time, prohibition was in full swing, causing the sale of alcohol to be illegal). Capone himself took in about $60 million dollars annually, an amount equal to $891 millions dollars today. The problem was Capone claimed he had no taxable income, and he never once filed a federal income tax return. Capone did not take the matter seriously, even bragging, “They can’t collect legal taxes from illegal money.” However, Capone would be proven wrong.