All > Original Photos > Historical Photos

Joe Aiello was a Sicilian-American mobster and prominent rival of Al Capone during the Prohibition era in Chicago. Born in 1890, Aiello rose to power as a leader of the Chicago Mafia and formed alliances with other Capone enemies, including North Side Gang leaders and New York's Joe Masseria. Aiello fiercely opposed Capone's dominance, particularly in the city's lucrative bootlegging operations. He repeatedly plotted to assassinate Capone, offering bounties to hitmen, but his attempts consistently failed. The rivalry escalated into violent gang warfare throughout the late 1920s. Aiello's ambition ultimately led to his downfall—after multiple failed plots, Capone's men ambushed and killed Aiello in 1930, riddling his body with bullets as he exited a Chicago apartment. Aiello’s death solidified Capone's supremacy over Chicago’s underworld.

Offered is a 6.5” x 8.5” original 1930 Head to toe photograph of famous rival to Al Capone, gangster Joe Aiello. The photo was issued as part of a series done by Underwood and Underwood of the most famous gangsters in America, all of whom were "At Large" when the photo was issued! A rare image of this famous gangster as he would be killed just months after this photo was issued, shot 59 times in an ambush by Capone's men in the streets of Chicago!