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Born in Pozzallo, Sicily, in 1899, Amatuna immigrated to the United States in the early 20th century, eventually arriving in Chicago's Little Italy. As a teenager he worked as a messenger for the Genna Brothers, a group of ruthless Sicilian gangsters. On February 21, 1916, at age 17, he earned a full membership in the Genna gang by murdering Frank Lombardi outside a saloon. Lombardi was a supporter of incumbent Chicago alderman John Powers, a bitter enemy of the Genna brothers. The brutal warfare between the Gennas and Powers became known in Chicago as the Aldermen's Wars.
Prohibition and the Bloody Nineteenth Ward
As Prohibition began in 1920, Amatuna had become one of the Gennas' leading members. The brothers continued to battle the Powers faction for political control of the Nineteenth Ward. When the Gennas began bootlegging operations, they became one of the main suppliers of homemade alcohol to the Torrio-Capone gang. Amatuna was the enforcer who oversaw production of the gang's numerous "alky cookers". By the end of 1920 Amatuna had become the personal bodyguard for "Bloody" Angelo Genna.
On September 28 a bomb exploded on the front porch of Powers' home. In spite of great damage, no one inside was hurt. Powers suspected that Amatuna was the bomber on orders from the Gennas. For the rest of 1920 and into 1921, Powers stationed armed guards and private detectives around his house as he campaigned against Anthony D'Andrea. Despite frequent bombings, Powers narrowly won the election. Enraged by his defeat, Angelo Genna blamed Paul Labriola, a municipal court bailiff and a Powers supporter, for convincing Sicilian and other Italian immigrants to support Powers. On March 9, 1921, Angelo, Amatuna and Genna lieutenant Frank "Don Chick" Gambino shot and killed Labriola. Although witnesses identified Genna and Gambino and the two men were charged with murder, the case was eventually dropped due to lack of evidence. Amatuna was later a suspect in the murders of Powers supporters Harry Raimondi and Gaetano Esposito.
By age 25 Amatuna had several bank accounts and held interests in various legitimate businesses. Earning the reputation of a "dandy", Amatuna was seen attending operas with Angelo and other gunmen, often wearing expensive diamond studs and cufflinks. Amatuna soon bought the Bluebird Cafe, a restaurant in Halsted Street in Chicago. He was said to have a pleasant tenor voice and often engaged in singing for his friends, and on occasion played short violin compositions. Confident that he was safe in the Bluebird, Amatuna never wore his two guns there. He once boasted to reporters that "no one can shoot me in here. This place is full of my friends. Any guy who would hurt me here would be torn apart by my patrons".
By the mid-1920s the Genna brothers were enmeshed in a vicious gang war with the North Side Gang, a primarily Irish gang run by Hymie Weiss. In May 1925 Angelo Genna was murdered by the North Siders. Now in charge of the Genna gang, Amatuna struggled to keep the organization from disintegrating. After Angelo's death, Amatuna walked into the headquarters of the Unione Sicilane, a powerful fraternal group under mob control, and declared himself president, which upset Al Capone. Although a Genna ally, Capone wanted to control the Unione Siciliane himself so that he, a Neapolitan, would be admitted to membership.
On the evening of November 13, 1925, Amatuna was preparing to attend the opera Aida at the Auditorium Theatre with his girlfriend Rose Picorara. Before the opera he visited a local barbershop on Roosevelt Road for a shave and manicure, his usual habit before going out for the evening. Upon arriving at the shop, owner Isadore Paul noticed the gang leader was without his bodyguards (Amatuna replied that he had not been able to reach them that day). As the owner applied a hot towel on Amatuna's face, two unidentified men rushed into the barbershop and drew their guns. The barber's screams alerted Amatuna, who quickly ducked behind the barber chair; however, he was shot in the chest twice during the gunfight as the gunman escaped. Taken to a local hospital, Amatuna requested that a priest marry he and Rosa; however, he died before the ceremony was completed.
Amatuna's elaborate funeral was one of many which would be seen between rival mobsters and, although many in Little Italy praised his generosity to local residents, Amatuna was feared for his brutal treatment towards the many Sicilian immigrants, many of them elderly, who worked the Gennas' alky boilers (often beating workers unconscious as a punishment for missing production quotas).
His body was soon dug up and taken back to Sicily, where he was re-interred in his native village of Pozzallo by his family. His death was greatly mourned in Sicily, as much of his income was given to his family and was used to repair a local church, which had long been in ruins.
The identities of the men who killed Amatuna were eventually revealed as North Side Gang members Vincent "The Schemer" Drucci and Jim Doherty (along with Frank Gusenberg as the driver); however, no charges were ever brought against them. The noted absence of Amatuna bodyguards Goldstein and Zion has also been questioned, but the question of whether they were paid off to stay away that night or if they had instead defected to the Northsiders, setting up Amatuna's murder themselves is still a matter for debate, as they were both killed shortly after his death (Zion, returning from Amatuna's funeral, on November 17 and Goldstein, who was killed with a shotgun in a drugstore by two unidentified gunmen, on November 25). The remaining Genna Brothers later commented that Amatuna's death was inevitable after he began hiring non-Sicilian bodyguards, disregarding tradition (Mike Merlo was said to have stated, "Them Jew boys only work for themselves and they will always side with the Irish in the end.").
It has been claimed that, as a result of Amatuna's death, it has been the practice of barbers to never put a hot towel over the face of a customer and have it always facing the front door so as to easily identify others entering the barbershop.
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