As the recognized leader of the post-Genna Sicilian underworld in Chicago, 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 and the national Unione (who had grown disgusted with Capone), Aiello allied with Bugs Moran's mob in an attempt to destroy Capone.
Giuseppe Masseria of New York, considered the "boss of bosses" of his day, attempted to mediate the conflict between Aiello and Capone in 1929 but only succeeded in offending Aiello (as well as his allies in Detroit, Buffalo and Brooklyn). During the early Castellamarese War, Aiello supported the forces of Salvatore Maranzano in New York against Masseria and Capone.
Aiello would have been on the winning side in the Castellamarese conflict, but he was killed by Capone's men on Oct. 23, 1930, near the corner of West End and Kolmar Avenues. A sketch above 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. The Aiellos were the heirs to the Genna organization of the early 1920s.
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