The Notorious Joseph Aiello (1890-1930)
By Hanna Houser and Dona Vitale
You already know about Al Capone. You may recognize names like Dean O’Banion or Bugs Moran. But do you know anything about Capone’s fiercest rival, Joe Aiello, who made his home in the peaceful Rogers Park Manor development in West Ridge?
Born in 1890 on the north coast of Sicily, Joe Aiello was among the affluent home buyers who flocked to the sparkling new West Ridge neighborhood when he built the largest home in the development at 2553 West Lunt across from Indian Boundary Park.
He was also a notorious gangster whose struggles to control the Sicilian Union and its control over Prohibition Era bootlegging drove him to bloody entanglements with Al Capone and his ally Tony Lombardo, who was Aiello’s former business partner.
The violence rocked the city, and did not end until Aiello’s own assassination, suspected to have been ordered by Capone, in 1930.
Before World War I, Chicago’s Crime Scene Centered on Vice
At the turn of the century, Chicago crime was concentrated in the Levee District, where illicit businesses such as The Everleigh Club — an upscale brothel — thrived in an atmosphere of open prostitution, drug use and gambling.
Operators of Levee businesses were the big-name gangsters of the time. Giacomo Vincenzo “Diamond Jim” Colosimo was no exception. After immigrating in 1895 from the Calabria region in the boot of Italy, he worked as a street pimp before he married an established brothel owner in 1902. Colosimo’s success in taking over her business translated into 200 brothel locations, some of which were upscale “resorts” where affluent men could engage in gambling, enjoy lavish food and drink, and be entertained by glamorous prostitutes.
Well-known by locals, Colosimo became the 1st Ward precinct captain, and organized the Street-Sweepers Union.
But his empire wasn’t managed without help. His wife Vittoria recruited family members to enforce his reign, including her nephew Johnny Torrio, who in turn imported a scrappy 20-year-old New Yorker in 1919 to help him do his job.
Torrio’s hire would drastically shape Chicago organized crime for the next decade and beyond. His name was Al Capone.[1]
The Aiello Family Joins the Wave of Immigrants from Italy
Meanwhile, Joe Aiello immigrated to the U.S. from Bagheria, a small town east of Palermo in the north of Sicily in 1907. He was 17.
On arrival, he joined his brother Andrea (Andrew) in Utica, New York, and was soon followed by two more members of the family, brothers Nunzio and Nicola. In 1910, the four Aiello brothers lived together in a Utica boarding house and worked as molders in a pipe foundry.[2]
During his time in Utica, Joe married Catarina Amara, who was also from Bagheria but had come from Sicily with her family as a child.[3]
They may have been cousins. Catarina’s mother was an Aiello, one of many with that name who came to America in this period, settling in New York, Chicago, and other locations.
In 1919, Catarina gave birth to their first child in Utica, but around then, according to reports published after he became a noted Chicago gangster, Joe had been involved in a shooting incident and fled Utica for Chicago. Catarina and baby son Carlo joined him in Chicago within a year, and second child Antonino was born in 1922.[4] A daughter followed in 1924, and another son in 1926.
We do not know much about Joe Aiello’s life when he first arrived in Chicago, but within a few years of his arrival, he had partnered with fellow Sicilian Tony Lombardo in a wholesale grocery business, importing fruits, cheeses, olive oil and other foods from Italy.
Prohibition Changes Everything
It’s almost certain that Lombardo and Aiello’s import/export business changed after January 17, 1920 when the 18th Amendment went into effect, kicking off the 13-year Prohibition Era that neither the business nor either of its two partners survived.
While some mobsters like “Diamond Jim” refused to get involved in the illicit alcohol trade, others saw Prohibition as a new opportunity, including Aiello and Lombardo.
In “Little Sicily,”[5] the immigrant community between Chicago Avenue and Division Streets west of Old Town, immigrants struggling to make a living became small home-based wine and liquor producers.
Aiello, Lombardo and others quickly recognized that an existing organization, the Sicilian Union, could serve as a vehicle for organizing these “bathtub gin” makers into recognized territories with hierarchies of management that became the new face of organized crime in Chicago.[6]
As importers and distributors of sugar, grapes and other ingredients required for production of alcoholic beverages, Aiello and Lombardo were in an ideal position to cash in, and soon engaged in the effort to organize small-time bootleggers by gaining control of the organization.
Yet, they maintained their “legitimate” businesses alongside their nefarious activities. In addition to Antonio Lombardo & Company, the food importing business, Joe Aiello and his brothers operated wholesale and retail bakeries in the heart of Little Sicily on Division Street.
The bakeries provided everything from bread to elegant pastries and wedding cakes and were a community staple among Italian immigrants. They also provided the perfect cover for bootlegging, and sales grossed $100,000 a year, the equivalent of about $1.6 million in 2024.
A Bloody Power Struggle: “The Beer Wars” Ensue
“Diamond Jim” Colosimo was murdered in his own empty restaurant on May 11, 1920, prompting the ascent to power of his enforcer, Johnny Torrio. To get a foothold on the North Side, Torrio partnered with Dean O’Banion, who promptly double-crossed him in a bid for control of a pre-Prohibition brewery at 1446 North Larrabee.
In retaliation, Torrio approved a hit on O’Banion, who was killed in his flower shop across the street from Holy Name Cathedral on November 10, 1924. The incident kicked off a six-year bar fight that intensified when Torrio ceded control of his gang to his young lieutenant, Al Capone.
As they maneuvered the Beer Wars and fought for power amongst Sicilian bootleggers, Aiello and Lombardo shifted from partnership to rivalry in 1926 — a split that came at a bloody cost in the citywide struggle for power, dominance and succession.
Lombardo allied with Capone, while Joe fought against Capone’s attempt to take over the Sicilian neighborhood, and allied himself with non-Italian northside gangsters O’Banion and his successors, Hymie Weiss and Bugs Moran.
Meanwhile, Joe Settles his Family in a Custom-Build West Ridge Home
As the conflict heated up, Aiello commissioned Alexander Capraro, the first Italian licensed architect in Illinois, to design a new home for his growing family in 1927.[7]
Likely looking for a luxurious refuge and bolstered by enormous financial success, he chose the lot at the southeast corner of Lunt and Rockwell in the new Rogers Park Manor development. In 1930, the jumbo 2-flat was valued at $65,000, double the next-most expensive homes in the affluent residential neighborhood.[8]
Aiello lived on the first floor with Catarina, their four children aged 10 to 2 years old, and Caterina’s sister Rose Amara.
The second flat was sometimes occupied by his brother Domenic and his family, and sometimes by other gangsters. In 1930, it was rented to Guiseppe Gagliardo, a fellow Sicilian who lived there with his wife and their seven children. Gagliardo reported his occupation as president of a labor union, but he was a member in good standing of the Aiello gang, arrested along with Joe’s brother Andrew and nine others in a 1929 police raid of a Loop office that produced evidence that Bugs Moran, Joe Aiello and Jack Zuta had become partners.[9]
In a 1930 report of a police visit to the residence, Aiello’s home was described as “sumptuously furnished with oriental floor coverings and drapes, expensive pictures and modernistic furniture but not a book in the whole house.”[10]
The Violence Continues and Intensifies
The same year the family moved to West Ridge, there was a violent attack on the Aiello bakery at 473 West Division Street. Drive-by gangsters wielding machine guns rained 200 bullets through the storefront windows on May 25, 1927, injuring Tony Aiello while Joe and Domenic escaped unharmed.[11]
Agitated and unsettled, Joe Aiello was out to kill. He began scheming to assassinate both Lombardo and Capone, at one point bribing a restaurant cook to poison their food. But fear of Capone was rampant. The cook alerted Capone and the plot was thwarted.
Up to this time, Aiello had managed to escape the attention of law enforcement, but as the violence escalated, he faced another major foe — the police. Against a backdrop of increasingly frequent assassination attempts and successful killings, Joe, his brothers and his enemies were more and more frequently “rounded up” in what was at least a show of police attempts to curb the violence, but few cases resulted in any serious prosecutions by the notoriously corrupt local authorities.
In November 1927, a plot to attack both Capone and Lombardo was exposed after police raided several locations, including an office at 7002 North Western Avenue, just two blocks down Lunt from Joe’s new home.
On the second floor of the building best known in recent times for the Lickety-Split Ice Cream shop on the first floor, police found 37 sticks of dynamite and other bomb making equipment, as well as rent receipts that led to the discovery of machine guns, ammunition, binoculars and other surveillance equipment in places set up for ambushes against both Capone and Lombardo. A “hit man” imported from Milwaukee as well as five members of the Aiello gang were arrested, and Joe was named by police and newspapers as a “new gang leader.”
Joe himself was hauled into police headquarters, and Capone gangsters, learning of his location, surrounded the station to intimidate him and his allies.
They did nothing that night, as the Chief of Police vowed to “kill the killers,” telling reporters “we’re not going to stand for any gang war in Chicago.”[12] Most of those involved on both sides of the battle went into hiding, and for a few weeks, there was calm.
On January 4, 1928, the Aiello bakery was struck once more, this time by two gunmen who walked in the door at the end of the day and started shooting. Dominic Aiello had returned to the business that afternoon, but was away when the gunmen arrived. His wife Grace and their three daughters were at home in an apartment upstairs and an employee who came out from the back room was not attacked.[13] The escalating war continued, as Joe, Dominic, Bugs Moran and others fled the city.
The Audacious Murder of Tony Lombardo
After two more presidents of the Sicilian Union were killed in 1927, Tony Lombardo finally achieved his goal of heading the organization by the end of the year. But, as the gang war continued, Lombardo was assassinated in the most significant gang killing since the murder of Dean O’Banion, and one of the most audacious crimes in Chicago history.
Lombardo was killed by an unidentified hit man at 4:30 p.m. on September 7, 1928 as he left the office of the Sicilian Union at the corner of Madison and Dearborn Streets. There was a crowd of more than 1,000 people gathered at the intersection, watching a publicity stunt staged by The Boston Store. The gawkers were all looking up at a small airplane being raised to a tenth floor window of the building, where it was to be on display inside the department store.
When shots rang out, confusion ran through the crowd and eyewitnesses were unclear as to exactly what had caused Lombardo’s bullet-riddled body to fall to the sidewalk in their midst. One of Lombardo’s bodyguards was also shot and killed, and a second, Joseph Lolordo, was held by police as the suspected shooter, a mistake that allowed the actual murderer to escape.
The Aiello brothers, as well as their associates in New York were suspected of the crime, but no charges were brought against them.[14]
Whether he ordered the hit or not, Joe’s fury was not abated by the death of his archrival. His next killing was even more ruthlessly audacious.
Exactly four months later, on January 7, 1929, three men paid a visit to Lombardo’s replacement as president of the Sicilian Union, Pasqualino Lolordo, who was the brother of Lombardo’s bodyguard.
Purportedly calling to discuss a possible truce, the three guests and their host spent an hour jovially drinking and toasting in the living room at 1921 West North Avenue while Mrs. Lolordo and a maid went about their household chores in the nearby kitchen.
Then, with no warning, shots rang out and Lolordo was hit eleven times in his own home. His wife, Aleina, rushed to his side as the three men fled. When questioned later by police, she said she knew nothing of her husband’s business, but picked out a photo of Joe Aiello as one of the three men who had called that day.[15]
A month later, the other two suspected assassins were killed along with five other Moran loyalists on February 14, 1929 – Chicago’s infamous St. Valentine’s Day Massacre. Joseph Lolordo was identified as one of the vengeful assassins, and Capone was suspected as being behind the hit.[16]
The Sicilian Union carried on despite the death of the president. They elected Joseph Guinta, who was soon slaughtered alongside two other Sicilian members of Capone’s gang. Who was thought to have ordered those murders? Joe Aiello, of course, although no charges were brought against him.
Aiello's Short-lived Victory Does Not Last
With the presidency of the Sicilian Union once again vacant, Joe was just about the last man standing when he returned to Chicago in May. His enemies had been eviscerated, he had control of the wholesale grocery business that provided a legitimate income of $100,000 a year and he controlled a network of bootleggers and extortionists that brought in many times that amount. He became president of the Sicilian Union, and survivors of the long gang war sought peace.[17]
Seeking a new way of hiding out, Al Capone pleaded guilty to a Philadelphia charge for possession of illegal weapons, and served a six-month term in the safety of a Pennsylvania jail.
But peace was short-lived. Gangster foes have long memories.
Late in 1929, police raids produced solid evidence of a business relationship between Bugs Moran, Aiello and Jack Zuta, the gang’s business manager. The raiders also found crime scene photos of the Valentine’s Day massacre they surmised were kept as motivation to seek revenge. On December 30th, 1929 Domenic and Andrew Aiello were arrested for questioning.[18]
Capone, having served his sentence, was released from jail on March 19, 1930.
As Capone prepared for his return to Chicago, Joe Aiello, Zuta and two other gang members were arrested in the Loop, apparently just for having ventured downtown. On April 24, they, along with Capone, Moran and twenty-four other gangsters were named as public enemies by the Chicago Crime Commission.[19] The heat was on.
On August 2, Jack Zuta was killed at a resort in Delafield Wisconsin, although he was not immediately identified as the victim of the hit. A crew of heavily armed gangsters barged into the hotel’s ballroom in the middle of the afternoon, guns ablaze. It was initially thought that the dead man was a Zuta lieutenant, but it proved to be the boss himself.[20]
Joe Aiello went into hiding and was not seen in Chicago for several months.
As part of the Zuta murder investigation, police raided the home at 2553 Lunt on August 21. Only Caterina and Grace were at home. Police discovered stacks of incriminating business papers, two shotguns, a rifle, shotgun shells, a box containing more than 100 keys, and two mattresses and bedding in the third-floor attic, where police guessed that Joe and Domenic may have been hiding out.[21]
Joe Aiello Meets a Bloody End
On October 23, 1930, an ambush at 205 North Kolmar Avenue, a mile west of Garfield Park, left a cascade of machine gunfire and brought a bloody end to Joe Aiello and his struggle for power. According to the Chicago Daily News, it was the sixty-first gang-related killing of the year.
After the assassination, newspapers reported that Aiello had been hiding out at the home of his close associate and company treasurer, Pasquale Prestogiacomo, AKA Patsy Presto, while making plans to flee to Mexico. On the evening of October 23, he summoned a taxi, and as he left the building to catch his cab, gunfire rained down from a second-floor window in the building across the street.
Aiello ran down a gangway next to the house to escape the barrage of bullets, but the hit had been carefully planned. Another shooter overlooking the site from the back of a third-floor apartment at 4518 West End Avenue finished the job. A third ambush site was later discovered.
Joe Aiello had met his end. The papers reported that a pound of bullets were removed from his body, and that more than fifty shots had shattered windows, furniture and walls in the Prestogiacomo apartment.[22] By the time police arrived, Prestogiacomo had disappeared, and went into hiding for several days before coming forward.
When questioned by police, Mrs. Prestogiacomo at first claimed Aiello had only been at her home one night, but after her eight-year-old daughter told police a different story, she admitted Aiello had been hiding there for several days. The investigation also revealed that Catarina Aiello had visited her fugitive husband at least once, and police hypothesized that the killers might have discovered his hideout by following her there.
As was common for gangster funerals, a crowd of more than 1,000 gathered on October 29 at the corner of Lunt and Rockwell to pass through a line of mourners in the living room and watch as Aiello’s $11,000 casket left his home and was taken to Mount Carmel cemetery for burial.[23]
The Aftermath: Aiello Family Scatters East and West
Immediately after Joe’s murder, Dominic and Grace Aiello fled to Italy with their three daughters, and did not attend the funeral. It is unclear how many other brothers, cousins and extended family members were in Chicago to pay their last respects. Most of the dead man’s immediate relatives eventually left the city.
Catarina sold the house on Lunt in February 1931 and moved to northern California, where other members of the Aiello clan as well as the Prestogiacomo family also settled.
She and her children left California a few years later, returning to upstate New York. She lived outside Rochester until her death in 1992, at the age of 93. She was interred in a family tomb in Rochester where she had moved Joe’s body several years earlier.[24]
Domenic, Grace and their daughters stayed in Italy for a year. They returned to Chicago in 1931 but left soon after for California. Domenic died there, in Santa Clara, in 1941. Grace lived until 1977.[25]
Prohibition ended on December 5, 1933. By then, Al Capone was serving time in federal prison for income tax evasion and the Great Depression was in full swing. The Roaring Twenties roared no more.
Sources
[1]For more on this period, see Tom Nall’s report of the RPWRHS walking tour, “The Gangsters of West Ridge” @ https://rpwrhs.org/2019/09/17/the-gangsters-of-west-ridge-a-walk-through-chicagos-roaring-20s/
[2] United States Census, 1910, Utica NY Ward 8, Enumeration District 0125, sheet 22B, Aiello brothers, lines 90-93
[3] Manifest of Alien Passengers, SS Citta di Napoli, arriving to port of New York from Palermo, July 9, 1903, Caterina Aiello and children Salvatore and Caterina Amare. Salvatore was age 8, Caterina was 4.
[4] Cook County Birth Certificate Index Record, Antonino Aiello, born July 13, 1922 in Chicago.
[5] A Brief History of Chicago’s Little Sicily Neighborhood and the Saint Philip Benizi Parish, by Calogero Lombardo provides an overview without discussing its role in Prohibition. See https://libblogs.luc.edu/ccic/little-sicily-st-philip-benizi-parish-fr-luigi-giambastiani/.
[6] A 2-part article in Crime Magazine by Allen May outlines the decade of struggle for control of the Unione Siciliana. See https://www.crimemagazine.com/chicagos-unione-siciliana-1920-%E2%80%93-decade-slaughter-part-one and https://www.crimemagazine.com/part-ii-chicagos-unione-siciliana-1920-decade-slaughter#google_vignette
[7] One of Capraro’s surviving buildings is Casa Bonita at 7340 North Ridge. For more about him, see https://blogginginitaly.com/tag/alexander-capraro-architect/ written by his grandson.
[8] United States Census, 1930, Chicago Ward 50, Enumeration District 16-1415, sheet 11B, taken April 10, 1930.
[9] “Raid Moran Den in Loop; 11 Captured,” Chicago Tribune, December 29, 1929, page 1.
[10] “Raid Aiellos’ Home; Guns, Papers Seized,” Chicago Tribune, August 21, 1930, pages 1-2.
[11] “Machine Guns Reopen Gang War,” Chicago Tribune, May 29, 1927, page 1.
[12] “Police Orders: ‘Kill Killers.’ Detectives Arm to End War for Vice Millions,” Chicago Tribune, November 22, 1927, pages 1 and 2, photos on page 46.
[13] “Gang Bullets Again Riddle the Aiello Brothers’ Bakery,” Chicago Tribune, January 5, 1928, page 3.
[14] The murder was front-page news in the Chicago Tribune and other papers on September 8, 1928 and for many days later as the investigation progressed. It was never proven who ordered the hit.
[15] “Kill Gang Leader in Home. Shot to Death by 3 Guests as Toast is Drunk. Victim is Successor to Tony Lombardo,” Chicago Tribune, January 9, 1929, page 1.
[16] The page one headline “Slay Doctor in Massacre” announced the murder to Chicago Tribune readers on February 15, 1929, and coverage by all Chicago papers went on for weeks as the investigation progressed.
[17] “Joe Aiello Back as Harbinger of Peace,” Chicago Tribune, May 30, 1929, page 3.
[18] “Raid Moran Den in Loop; 11 Captured,” Chicago Tribune, December 29, 1929, page 1,previously cited.
[19] List 28 as ‘Public Enemies:’ Crime Board Ask Exile of Gang Leaders,” Chicago Tribune, April 24, 1930 page 1.
[20] “Gang Kills at Hotel Dance,” Chicago Tribune, August 2, 1930, pages 1-2.
[21] “Raid Aiellos’ Home; Guns, Papers Seized,” Chicago Tribune, August 21, 1930, pages 1-2.
[22] The murder was front-page news in most Chicago papers. One of the most vivid immediate accounts was in the Chicago Daily News, October 24, 1930, pages 1 and 3. The Chicago Tribune also featured extensive coverage, including a diagram of the crime scene The Chicago Daily Times, a tabloid newspaper, carried multiple pages of stories and photos about the crime and the investigation for several days, as did the Chicago Tribune and other papers nationwide.
[23] “Morbid Crowds See Aiello To His Grave,” Chicago Daily Times, October 29, 1930, page 2.
[24] Death notice: Catherine Amaro Aiello, Rochester Democrat and Chronicle, December 5, 1992, page 6.
[25] Find-A-Grave Memorial ID 6007537, Domenico Aiello, Died January 26, 1941. Headstone also shows Grace Aiello, died November 12, 1977. @https://www.findagrave.com/memorial/60075307/domenico-aiello
About the Author: Hanna Houser
Hanna Houser, a 2024 student intern with RPWHS, is drawn to history because it helps interpret modern life in the context of what came before. Houser was a May, 2024 graduate of Loyola University majoring in Multimedia Journalism with a minor in Political Science. During her school years, she was heavily involved with The Loyola Phoenix, the campus newspaper. Houser first moved to Rogers Park for school and lived in the neighborhood for four years. Prior to moving to Rogers Park, she spent time living on both the east and west coasts. After graduation, she returned east to pursue a career in investigations at a financial investment firm.
About the Author: Dona Vitale
Dona Vitale has been involved with the Rogers Park/West Ridge Historical Society since 2012, and a member of the Board of Directors since 2014. She lived near the Loyola University campus in Rogers Park from 1979 to 2014, when she retired and moved a mile south. She continues to volunteer with RPWRHS, acting as team leader for the Property History Quest (PHQ) project, and created the Noted and Notorious series as way to share the many fascinating stories of mostly unknown neighborhood residents brought to light by the PHQ research team.