While Al Capone’s Outfit was fighting its way to the top of Chicago’s underworld, one of his chief rivals was the mafioso Joe Aiello. Aiello was president of the Unione Siciliane, synonymous with the Mafia in Chicago. For this reason alone, he earned the title of “the boss of the Sicilian Mafia in Prohibition-Era Chicago.” Beyond the Windy City, Aiello had powerful friends in Detroit and New York City, where he affected the outcome of the 1930 Castellammarese War.
Joe was born Giuseppe Aiello in Bagheria, a suburb of Palermo, in 1890. At seventeen, he sailed to New York, joining two older brothers, Nunzio and Andrea, upstate in Utica. A halfway point between Lake Ontario and Albany along the Mohawk River, Utica drew a large immigrant population to work in manufacturing and transport. Among them were Sicilian merchants, some of them associated through family and business ties with the nascent Mafia in Utica. Fruit wholesalers, in particular, were closely tied to one another and organized crime. It may have been while Aiello lived in Utica that he formed ties with the Maggadino Family in Buffalo.
Joe Aiello and his partner in a Utica saloon, Sam La Fada, were charged in 1917 with firing upon Antonio Gagliano, a competing saloon owner. Aiello tried hiding from the police in the home of his father- and brother-in-law, who were charged with interfering with a police officer. Aiello was found in possession of a recently fired handgun, and a license to carry. La Fada was killed in Buffalo a few months later.
It’s often reported that Aiello left Utica after taking part in the 1917 shooting. Joe was married to Caterina Amara. Their daughter, Lena, was born late in 1918. Son Carlo was born in Utica in 1919. A news item about the scalding death of Joe’s daughter, in March 1921, shows the family still living on Bleecker Street in Utica. Two and a half year-old Lena Aiello ran into her mother and maternal grandmother, who had just boiled water for the family’s baths. She survived for five hours.
Joe moved his family to Chicago shortly after this tragedy. Their next child, Antonino, was born in Chicago in July 1922.
Joe’s brothers moved to Chicago ahead of him, starting with the oldest, Nunzio, who married there in 1916. Andrea, also married, registered for the draft from a Near North Side address the following year. Nunzio’s address on Locust Street was in Little Sicily, also in Chicago’s Near North Side.
In the years leading up to Prohibition, Chicago’s criminal underworld was still broken up into neighborhood territories. “Big Jim” Colosimo’s network of brothels was beginning to encroach on these boundaries, but there was not yet a monopoly on criminal power, and there was no overarching leadership: not among organized criminals, nor even among mafiosi in the city.
The Genna brothers, from Marsala, Sicily, were one of the earliest Mafia families in Chicago. They were based in Little Italy, in the Near West Side. To the east of the Genna territory was Goose Island, where the Irish North Side Gang ruled. The Gennas controlled the Unione Siciliane and fought the Irish gang, led by Dean O’Banion. On the other side of Goose Island was Little Sicily, where a Corleonese Mafia family was dominant. The Nicolosi brothers ruled from their Gault Court saloon, a territory they inherited from their murdered father-in-law.
In Chicago, the Aiello family worked for the railroads, then became fruit dealers, and owned bakeries and at least one confectionery shop. Father Carlo Aiello, a fruit merchant, arrived from Bagheria in 1920 and died in Chicago three years later.
Joe Aiello began his ascent to power by partnering with Antonio Lombardo of the Unione, but then alienated his patron when he made an alliance with Bugs Moran, who was O’Banion’s successor in the North Side Gang. The Gennas were killed by the Irish gang in 1925. Joe and his brothers took over the old Genna brothers’ territory: in particular, control of the Unione. Allied to the North Side, the Aiello gang became prominent targets for Al Capone’s Outfit.
The Outfit was never part of the Sicilian Mafia. Its members were engaged in organized crime, and most of them were Italian or Italian-American, but they were not part of the same organization as the Genna, Nicolosi, and Aiello families, who all came from Sicily. Only after the Commission was formed, after the Castellammarese War, did the Outfit become part of an American Mafia, on equal footing with Sicilian American Mafia families.
By 1927, the tension between the Outfit and Joe Aiello’s family reached a breaking point. The Aiello family bakery in Little Sicily was riddled with bullets in a drive-by attack. Joe, who had already made multiple attempts on Capone’s life, was forced to leave Chicago. Regardless, he won the presidency of the Unione Siciliane the following year. In 1928, Aiello enjoyed the support of the Nicolosi brothers, but their representative at the Cleveland Conference, Sam Oliveri, lost a brother to Capone’s men, and was afterward suspected by police of brokering a new deal that cut out the Aiello family.
The power that emanated from New York City was felt everywhere by the Mafia. Al Capone and several of his closest associates in the Outfit were from New York. One of them was “Little Davey” Petillo, a native of New York City. As a young man, Petillo worked with Lucky Luciano as a hitman, narcotics trafficker, and pimp. After working for Joe Aiello in Chicago, Petillo rejoined his New York associates in the Outfit, and was Al Capone’s bodyguard at Aiello’s death in 1930.
Meanwhile in New York City, Joe “The Boss” Masseria’s power was growing and threatened to encompass all Mafia activity in the United States. Aiello had long been aligned with Salvatore Maranzano and the other mafiosi from Castellammare del Golfo, including Gaspar Milazzo in Detroit, and Maggadino in Buffalo: both Mafia bosses who’d started out in the Castellammarese stronghold of Williamsburg, Brooklyn. Masseria came to openly support Capone’s bid for control over Chicago, widening the partisan divide throughout the Mafia in America, in the lead up to the Castellammarese War. Aiello financed Maranzano’s campaign against Masseria through the summer, before falling to Capone’s hitmen in October. Joe was forty.
Lucky Luciano turned on first Masseria, and then Maranzano, before assuming a consciously more modest position than either predecessor as a leader among equals in the new American Mafia. In Luciano’s Commission, Al Capone was the representative for the city he finally dominated, though not for long. In 1931, Capone was charged with tax evasion, and he spent the rest of his life in prison.