Final answer:
Al Capone, a notorious crime boss during Prohibition, was never prosecuted for bootlegging but was convicted of income tax evasion, resulting in an eleven-year prison sentence.
Step-by-step explanation:
During Prohibition (1920-1933), city crime bosses sold illegal alcohol to willing buyers through intimidation. Chicago's Al Capone was never prosecuted for money laundering, insider trading or bootlegging. However, he was prosecuted for income tax evasion.
Capone's criminal operation, known as the Chicago Outfit or Chicago mafia, was extensive and included illegal activities such as bootlegging, prostitution, and gambling. Despite the notorious violence and crime associated with his empire, Capone was ultimately brought down by his failure to pay taxes on his considerable income, leading to an eleven-year prison sentence, part of which was served at Alcatraz.