Born in Bagheria, Sicily, Aiello was one of 10 boys in his family. In July 1907, Aiello immigrated to the United States to join various members who were already there. The Aiello family set up a number of businesses in both New York and Chicago. They became importers of groceries such as olive oil, cheeses, and sugar. Aiello was the co-owner of a cheese importing business alongside a fellow Sicilian, "The Scourge" Antonio Lombardo. The Aiello's also opened a bakery and a confectionery shop. With the enactment of Prohibition and beginning of bootlegging, the sugar import business brought the family into contact with organized crime. In Chicago, the Aiello family began supplying sugar to gangs illegally distilling spirits, a territory previously occupied by the Genna family, a Sicilian-American criminal gang.
War with Capone Edit
At that time, a benevolent society called the Unione Siciliana was set up to help Sicilian immigrants settle in the United States. While the Unione was originally intended for legitimate charitable purposes, it was soon taken over and corrupted by Sicilian gang members. Unione officials soon began demanding "protection money", or tributes, from its members, promising retribution to those who refused to pay. Al Capone wanted to control the Unione, but he was barred from even joining it because his background was Neopolitan, not Sicilian. The head of the Chicago branch of the Unione was Sicilian Mike Merlo, a bootlegger who used his position at the Unione to mediate disputes among the Chicago gangs. The death of Merlo in November 1924 reignited Capone's ambitions to control the Unione. Lombardo, a Capone ally, became the new head of the Chicago branch. Lombardo's success angered Aiello, who had also wanted this job.
In addition to the Unione Siciliana position, Aiello was also angry at Lombardo due to a long disagreement over control of their cheese importing business. At this stage, Aiello decided to eliminate both Lombardo and Capone. Aiello tried without success to assassinate Capone. On one occasion, Aiello stationed a gunman with a submachine gun across the street from Capone's favorite cigar shop, but he was spotted in time. On another occasion, Aiello offered the chef of Capone's favorite restaurant, "Diamond Joe" Joseph Esposito, $35,000 to put prussic acid in Capone's soup. Instead, Esposito exposed the plot to Capone. During the summer and autumn of 1927, a number of hitmen hired by Aiello to murder Capone were themselves slain.
Police raided a number of addresses and arrested numerous Aiello associates, including Milwaukee gunman Angelo La Mantia, who confessed that he had been hired by Aiello to kill Capone and Lombardo. Aiello himself was then picked up by police and taken to South Clark Street police station. Capone heard of the arrest, and dispatched a large team of gunmen to stand guard outside the station, ostensibly to await Aiello's release. Three Capone gunmen, including "Little New York" Louis Campagna, then got themselves arrested near the front of the station, probably intentionally, for having been placed in the cell next door to Aiello they duly informed Joe that he was as good as dead. Pleading for 15 days' grace to sort out his affairs and leave the city, Aiello was given police escort out of the building and appeared to do just that, disappearing to New Jersey with some of his brothers.
Alliance with the North Side Gang Edit
Aiello had recently taken up an alliance of sorts with George "Bugs" Moran, an enemy of Capone from the North Side Gang of Chicago. Two of Moran's hitmen, the brothers Frank "Tight Lips" Gusenberg and Peter Gusenberg, were soon given the task of removing Antonio Lombardo, which they succeeded in doing on a busy Chicago street on September 7, 1928. Though never arrested for the crime, they appear to remain the chief suspects to this day, in that as well as the murder of Lombardo's successor as head of the Unione Siciliana, Pasqualino Lolordo.
Still believing he had a chance to take the throne himself, and apparently ignoring the fact that it appeared to be a somewhat dangerous position to occupy, Aiello was due to attend a mob meeting at the Statler Hotel in Cleveland, at which the Unione Siciliana leadership would be discussed. Allegedly, Aiello elected instead to inform the police of the meeting, leading to the arrest of 23 apparent mob figures, including such notables as Joe Profaci and Joseph Magliocco.
The murder of Lolordo was the next major event in the battle for control of the Chicago mob, and again Aiello was believed to have masterminded the killing, as with that of Lombardo. Capone had long ago had enough of Aiello and Moran, and retaliated with the St. Valentine's Day Massacre, a hit that wiped out the Gusenberg brothers and their regular partner-in-crime James Clark, two other Moran men but not Moran himself. The shooting decimated Moran's forces (he was effectively removed as a threat at this point) and removed almost all support Aiello had banked on in recent months. But the massacre had another side to it as well. True, Moran's forces had been weakened, but he himself survived the attack. With the remainder of his gang, he managed to keep his territory through the end of prohibition and the early thirties. The massacre did one thing that Capone did not expect - bring down the big man himself. After the massacre, the government went after Capone with everything they had. They were able to get him on tax evasion charges and ship him off to prison, effectively ending his reign as boss.
Aiello then turned to Capone killers Albert Anselmi and John Scalise, as well as the new head of the Unione, Joseph "Hop Toad" Giunta, trying to convince them that they would all be winners were Capone wiped out, with Aiello himself taking over the North Side of Chicago following the departure of Bugs Moran. But in April 1929, getting wind of the plot, Capone beat them to the punch and had the three men killed (the scene famed by a number of movies in which Capone murders associates with a baseball bat at a banquet is based on the killings of Anselmi and Scalise).
Head of the Unione Siciliana Edit
Remarkably, Aiello then finally got his chance to head up the Unione Siciliana himself. A conference in Atlantic City of numerous mob bosses saw Aiello's promotion as the only way to restore order in Chicago, and Capone apparently accepted this, at least temporarily.
Aiello's time in charge coincided with Capone serving a year in prison for carrying a concealed weapon. Aiello, ever a man to bring misery onto himself, duly saw this as an opportunity to scheme yet again for Capone's permanent retirement. When Frank J. Loesch, chairman of the Chicago Crime Commission compiled his "Public Enemies" list of the top 28 people he saw as corrupting Chicago in April 1930, Capone headed the list, while Aiello was ranked in seventh place. The list was widely published gaining Aiello a measure of nationwide notoriety.
The rumors and gossip eventually got back to Capone, who resolved to finally eliminate Aiello. Several Aiello associates were wiped out during 1930, including Peter "Ashcan" Inserio and Aiello bodyguard Jack Costa. Meanwhile, Aiello hid in the Chicago house of Unione Siciliana treasurer Pasquale Prestogiacomo.
On October 23, Aiello was making plans to permanently leave Chicago, allegedly to move to Mexico. Upon leaving Prestogiacomo's building, a gunman in a second-floor window across the street started firing at Aiello with a submachine gun. Aiello toppled off the building steps and moved around the corner, out of the line of fire. Unfortunately for Aiello, he stumbled into the range of a second submachine gun nest on the third floor of another apartment block. Aiello was taken to Garfield Park Hospital, but was pronounced dead on arrival. The coroner eventually removed 59 bullets from his body.
Before eventually being placed in Riverside Cemetery in Rochester, New York, Aiello was originally buried in Mount Carmel Cemetery in Chicago on October 29, 1930, close to former friend and foe Lombardo. Aiello's funeral lacked the show of many organized crime funerals of the age; the cars filled with mourners and police on motorcycles who started the trip from Aiello's home disappeared before reaching the cemetery. Besides the hearse, all that remained of the procession was a car containing Aiello's widow Catherine and three Ford Sedans containing flowers.