Born in Brooklyn, New York, to Italian immigrant parents, the legendary Al Capone became a gangster known for his domination of Chicago organized crime between 1925 and 1931. Al Capone was the fourth of nine children whose father, Gabriele Capone, owned a barbershop. Expelled from school in the sixth grade for hitting a teacher, Capone continued to live with his parents and siblings, working to help support the family. Described as a well-behaved and sociable boy, Capone nonetheless joined a series of neighborhood gangs. In one gang-related skirmish in a brothel-bar, Capone's enemy slashed his left cheek with a knife or razor; years later Capone would receive the nickname "Scarface." Capone also ran errands for New York City gangster Johnny Torrio, earning pocket money and learning invaluable lessons in organized crime that would later serve his gangster empire in Chicago.

Torrio moved to Chicago in 1909 and asked Capone to join him there ten years later. Torrio soon became the leader of a large Chicago brothel business; later, when Prohibition outlawed liquor, bootlegging became Torrio's lucrative organized crime of choice. Torrio retired in 1925 and Capone became his successor. Capone's crime rackets involved gambling, prostitution, and bootlegging. He minimized his business competition, rival gangs, by gunning them down. Capone's most notorious machine gun massacre happened in a north Chicago garage on February 14, 1929, and became known as the St. Valentines Day Massacre.

Capone's organized crime reign ended in June 1931, when he was indicted for federal income tax evasion. Found guilty, Capone was sentenced to 11 years in prison. He began his sentence in an Atlanta penitentiary in May 1932, but in August 1934 Capone was transferred to Alcatraz, becoming that prison's most famous prisoner. Capone was released from his sentence in 1939, suffering from an advanced case of syphilis. He received treatment in a Baltimore hospital. Capone then retired and became a recluse on his Palm Island, Florida estate. He died in 1947.