The story of Giuseppe "Joe" Aiello is a definitive chapter in the Prohibition-era "Beer Wars" of Chicago. He is best remembered not just as a powerful bootlegger but as the man who came closer than anyone to successfully assassinating Al Capone.
Background and Early Life
Joe Aiello was born in Bagheria, Sicily, in 1890. He immigrated to New York City in 1907 before eventually settling in Chicago. Unlike many "street-level" thugs, Aiello came from a large, tight-knit family; he operated alongside his nine brothers and numerous cousins, creating a formidable clan that dominated the city's West Side.
The Aiellos initially ran a legitimate business importing olive oil, cheese, and sugar. However, during Prohibition, that sugar business became the backbone of a massive illegal distilling operation.
Criminal Activities: The Sugar King
Aiello was the leader of the Aiello-Zuta Alliance, a coalition of Sicilian mobsters and Jewish gangsters (led by Jack Zuta).
Distilling Monopoly: He controlled the supply of corn sugar and industrial alcohol to independent moonshiners across Chicago.
Political Influence: Through bribery and intimidation, he exerted significant control over the Unione Siciliana, a powerful benevolent society that served as a political front for the Sicilian Mafia.
The Rivalry with Al Capone
The central theme of Aiello’s criminal career was his absolute hatred for Al Capone. This wasn't just business; it was personal and ethnic. Aiello, a "Mustache Pete" (an old-school Sicilian), viewed Capone—a Neapolitan—as an outsider who had no right to lead Sicilian organizations.
The Assassination Plots
Aiello spent much of the late 1920s trying to kill "Scarface":
The Chef Bribe: In 1927, Aiello offered the chef at Bella Napoli Cafe (a favorite Capone hangout) $10,000 to put prussic acid in Capone's soup. The chef informed Capone instead.
The Bounty: Aiello reportedly placed a $50,000 bounty on Capone's head, which led to several drive-by shootings targeting the Outfit leader.
The Hired Hitmen: He hired professional assassins from outside Chicago to eliminate Capone, but Capone’s intelligence network (and his enforcer, Jack McGurn) neutralized almost all of them before they could strike.
Investigations and Arrest
Aiello was frequently detained by Chicago police, but rarely for long. His most famous "arrest" occurred in 1927 after a botched hit on Capone. While Aiello was in custody at the police station, dozens of Capone’s gunmen surrounded the building, waiting for him to be released so they could kill him. Police eventually had to escort Aiello out through a back exit for his own safety.
The Violent End (October 23, 1930)
Capone eventually grew tired of the constant threats. On October 23, 1930, Aiello was hiding out in an apartment on North Kolmar Avenue.
As he exited the building to get into a taxi, he was ambushed by gunmen positioned in two different second-story windows across the street.
The Overkill: Aiello was struck by at least 59 bullets from Thompson submachine guns and shotguns.
The "Signature": The sheer volume of lead used in the hit was a classic Capone "outfit" signature, meant to send a message to any remaining Aiello loyalists.
Aftermath and Current Status
The Power Vacuum: With Joe Aiello dead, his brothers fled Chicago or retired from the life. Al Capone finally gained undisputed control over the Unione Siciliana, solidifying his hold on the city's Italian underworld.
The Mob Evolution: Aiello's death marked the end of the "old school" Sicilian clan dominance in Chicago, paving the way for the multi-ethnic "Chicago Outfit" structure that persists in history books today.
Current Status: Joe Aiello is buried in Mount Carmel Cemetery in Hillside, Illinois—ironically, the same cemetery where Al Capone was later interred.
His legacy remains that of the "persistent challenger"—the man who refused to bow to the most famous gangster in history and paid the ultimate price for it.

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