Sept. 27, 1890, to Oct. 23, 1930.
Aiello was the boss of the Sicilian Mafia in Prohibition-Era Chicago. While Alphonse Capone is widely regarded as Chicago’s “Mafia” leader, Capone was not Sicilian and was not widely accepted by Sicilian Mafiosi (hence his obsession with dominating the Unione Siciliana brotherhood and with opening that group’s membership to non-Sicilian Italians).
Immigrant Aiello initially settled in Utica, an upstate New York community located about halfway between Albany and Rochester. About 1920, Aiello headed westward to Chicago and eventually became the acknowledged head of the post-Genna Sicilian underworld there.
During Prohibition, Aiello controlled much of the criminal element in the city’s Little Sicily, including its home liquor-making establishments, and was a thorn in Capone’s side. He actively worked to be more than just a thorn and in the late 1920s, possibly with the approval of Brooklyn’s Frank Yale, a former close friend of Capone, and the national Unione (who had grown disgusted with Capone’s meddling), Aiello allied with Bugs Moran’s mob in an attempt to destroy Capone.
The gang war did not go well for the Aiello forces, and the family leadership left Chicago for a time. The Aiello’s reportedly found sanctuary in New Jersey or in Yale territory in Brooklyn, NY.
The Aiello leadership returned to Chicago in 1928 after Yale was killed. The family was blamed for the assassinations of Capone-sponsored Unione Siciliana leaders Antonio Lombardo and Pasquale Lolordo.
After the assassination of Lolordo in January 1929, Aiello stepped up to the coveted but terribly hazardous position of Unione president.
Giuseppe Masseria of New York, the “boss of bosses” of his day, attempted to mediate the conflict between Aiello and Capone early in 1929 but only succeeded in offending Aiello (as well as his allies in Detroit, Buffalo and Brooklyn). During the early Castellammarese War, Aiello (a native of Bagheria, a wealthy suburb of Palermo) supported the forces of Salvatore Maranzano in New York against Masseria and Capone.
Aiello would have been on the winning side in the Castellammarese conflict (momentarily), but he was killed by Capone’s men on Oct. 23, 1930, near the corner of West End and Kolmar Avenues. A sketch at right shows that shots were fired from two adjacent residences across the street from Aiello’s waiting taxicab.
Joe Aiello had several brothers who also participated in bootlegging and other Mafia endeavors. Tony Aiello was injured in a Capone attack.