On the evening of October 23, 1930, Joe Aiello walked out of a West Side apartment building in Chicago and into a planned crossfire. He was a Sicilian-born bootlegger and one of Al Capone's most persistent enemies. Police and newspapers immediately suspected Capone's organization.
No one was ever convicted, and the documented record does not establish who fired the guns or who gave the order. This article separates what is documented about the ambush, the feud behind it, and the failed investigation from what remains allegation or theory.
The ambush on North Kolmar Avenue
Aiello was killed at 205 North Kolmar Avenue, about a mile west of Garfield Park. Aiello had been hiding there in the apartment of Pasquale "Patsy Presto" Prestigiacomo, treasurer of Aiello's importing company. (Some sources spell the surname Prestogiacomo.)
The Chicago Tribune of October 24, 1930, put the time of the shooting at about 8:30 p.m., according to an excerpt reproduced in Gina Vozenilek's family memoir of the case. The same excerpt describes Aiello as caught in a crossfire from two gun nests.
The sequence reconstructed from the Wikipedia account, which cites Tribune and New York Times coverage, runs as follows:
- Aiello stepped out of the building to enter a waiting taxi.
- A gunman with a submachine gun in a second-floor window across the street opened fire.
- Aiello was reportedly hit at least 13 times before he toppled off the steps and moved around the corner, trying to get out of the line of fire.
- That path took him into the range of a second submachine gun on the third floor of a neighboring apartment block, where he was finished off.
- The two apparent shooters fled in a Ford sedan, which was later found burned.
- Aiello's body was taken by taxi to Garfield Park Hospital, where he was pronounced dead.
Police later found a third gun position, in another nearby building, that was not used. According to the same account, a man who gave the name Lon Celespe had rented it about a week before the killing.
The two firing rooms were rented under the names Morris Friend and Henry Jacobson.
The taxi driver, James Ruane, told the Tribune that he saw a second-floor window sash slide up and "a cumbersome looking instrument" lifted to the sill, as quoted in Vozenilek's account.
He ducked behind his cab door and was unhurt.
Contemporary counts of the wounds vary:
- The Tribune excerpt reproduced by Vozenilek cites 35 steel-coated bullets.
- TIME's report a week later said Aiello fell "with 57 holes and more than a pound of lead in him."
- Wikipedia says the coroner removed 59 bullets weighing over a pound.
All of them agree on the overwhelming force of the attack, and none of the figures should be treated as exact. The shooters' identities were never established.
Who Aiello was and what he stood to lose
Aiello was born in 1890 in Bagheria, Sicily. According to the Rogers Park/West Ridge Historical Society, he emigrated to the United States in 1907, worked in a Utica, New York, pipe foundry with his brothers, and reached Chicago around 1919 to 1920.
There he partnered with fellow Sicilian Tony Lombardo in a wholesale grocery business importing fruits, cheeses, olive oil and other foods.
Prohibition, which began in January 1920, changed what that business could be, opening a far more lucrative market in supplying illegal alcohol.
The same account says the partners were well placed as suppliers of sugar, grapes and other ingredients to home-based alcohol producers in Chicago's "Little Sicily." They also saw that the Sicilian Union, an existing community organization, could organize small bootleggers into territories with a management hierarchy.
Aiello and his brothers also ran bakeries on Division Street, which the historical society says provided cover for bootlegging, with sales of about $100,000 a year.
The Unione Siciliana mattered because its presidency carried real influence over both community affairs and criminal politics. Lombardo, Aiello's former partner, wanted that presidency, and Aiello opposed the control Capone's allies exercised over it. Of the Sicilian Union's presidents in this period, Allan May's history of the organization notes that all eight men who held the post during the 1920s died, and seven were murdered.
Aiello's finances showed what was at stake. He built a large two-flat at 2553 West Lunt Avenue in West Ridge, valued at $65,000 in the 1930 census, double the next most expensive homes in the area, according to the historical society. Later, Aiello's company at the time of his death, the Italo-American Importing Company, was described by police as handling more than $23,000 a month in yeast and sugar, "most of this" going to illicit liquor makers, in a Washington Post report quoted by Vozenilek.
A feud with Capone rooted in power and territory
The conflict grew out of a split among Sicilians, not a simple north-south gang dispute. The historical society's account says Aiello and Lombardo shifted from partnership to rivalry in 1926.
Lombardo allied with Capone. Aiello resisted Capone's attempt to take over the Sicilian neighborhood and aligned himself with the non-Italian North Side gangsters descended from Dean O'Banion, including Hymie Weiss and later Bugs Moran.
Three violent episodes defined the escalation, and responsibility for each is more contested than popular retellings suggest:
- The bakery attacks. Gunmen fired about 200 bullets into the Aiello Brothers bakery on Division Street in May 1927, injuring Tony Aiello. The bakery was shot up again in January 1928.
- The Lombardo killing. Lombardo was shot dead on September 7, 1928, outside the Sicilian Union office at Madison and Dearborn in front of a crowd. The historical society says the Aiello brothers and their New York associates were suspected, no charges were brought, and it was never proven who ordered the hit.
- The Lolordo killing. Lombardo's successor, Pasqualino Lolordo, was shot eleven times in his home in January 1929 while sharing a toast with three visitors. Early reports said his widow picked out Aiello's photograph. May's account, however, cites a deputy police chief who said she identified no one, and he calls the question of whether Aiello was present unresolved.
The date of the Lolordo killing itself varies between sources, January 7 in some and January 8 in others. Wikipedia says Aiello is believed to have masterminded the Lolordo murder and, with Moran, that of Lombardo. It also says the Lombardo killing prompted Capone to retaliate through the St. Valentine's Day Massacre. These are historians' interpretations and police allegations, not court findings.
Plots attributed to Aiello against Capone are likewise described as alleged. The historical society reports that he bribed a restaurant cook to poison Capone and Lombardo, a plot that failed when the cook alerted Capone. Vozenilek's account puts the offer at $35,000 to a chef at the Bella Napoli Café.
In November 1927, police raided an office at 7002 North Western Avenue and found dynamite and ambush equipment, and they publicly named Aiello a "new gang leader."
By 1929, according to the historical society, Aiello had outlasted many enemies and became president of the Sicilian Union after returning to Chicago in May 1929. Peace did not last.
Police raids in late 1929 produced evidence of a business tie among Moran, Aiello and Moran's business manager Jack Zuta. In April 1930 the Chicago Crime Commission named Aiello, Capone, Moran and others as public enemies. Wikipedia says Aiello ranked seventh on that list.
Hiding, surveillance, and the final days
Zuta was killed on August 2, 1930, at a Wisconsin resort. According to the historical society, Aiello then went into hiding and was not seen in Chicago for several months. Police raided his West Ridge home on August 21 as part of the Zuta inquiry and found two shotguns, a rifle, shotgun shells, more than 100 keys, stacks of business papers, and mattresses in the attic, where they guessed Aiello and his brother Domenic had been hiding.
By October, Aiello had taken refuge at Prestigiacomo's apartment on Kolmar Avenue. Wikipedia, citing Chicago Tribune reporting, says he moved in on October 13. Prestigiacomo told police Aiello came about ten days before the shooting, as quoted in Vozenilek's article, while family lore told to Vozenilek held it was two weeks.
Aiello rarely left the apartment.
Reports said he was preparing to leave Chicago permanently, apparently for Mexico. That was a reported plan, not a confirmed destination, and Prestigiacomo later told police Aiello was simply going out for a barber's appointment. Vozenilek's family account adds that her grandfather, then 13, pretended to sleep while Aiello was overheard saying that Chicago was too "hot" and that he was going to Mexico the next day. That is a family recollection, decades old.
How the killers found Aiello is also unproven. The historical society notes that his wife Catarina visited him at least once, and police hypothesized that the killers might have followed her. Wikipedia attributes a similar theory to Frank Nitti biographer Mars Eghigian Jr. That remains a theory.
The investigation: suspicion without proof
Police and prosecutors suspected Capone almost at once. TIME reported that the trap resembled the one that killed North Side leader Hymie Weiss, a killing credited to Capone, so police announced that Aiello's slayers were "Caponemen." Wikipedia adds that investigators noted the precision machine-gun ambush was typical of his attacks, and that Nitti was wanted for questioning.
Suspicion is the right word. None of the accounts cited in this article presents evidence tying a named Capone associate to the shooting.
Other possibilities surfaced in contemporary reporting. Wikipedia notes that at least one press story speculated Moran could have been behind the hit, and that some historians later suggested outside Mafia forces linked to New York's Castellammarese War.
It also says that Chicago-crime expert Virgil Peterson believed the killing was strictly a matter of local gang warfare. Moran, who had been released on bail just hours before Aiello's killing, called Aiello a "double-crosser" and said he had not seen him in eight months, according to Vozenilek's reproduction of Tribune coverage.
Scrutiny fell hard on Prestigiacomo. The documented points:
- He went into hiding after the shooting, then turned himself in after about three days.
- He was charged as an accessory before the fact, as was John Sorce, an employee of Aiello's import company.
- The New York Times reported that some investigators believed he had given the Capone gang information about Aiello's location, and the Washington Post reported that a locksmith said Prestigiacomo had removed his front doorbell, making it harder for the cab driver to find the right apartment. Both are police beliefs and reported claims, not findings.
- Prestigiacomo denied any betrayal, saying he sheltered a friend and never questioned him.
- The case went to a grand jury and was dropped, reportedly on January 29, 1931.
Vozenilek is Prestigiacomo's great-granddaughter, and her account is a family memoir that she cross-checks against newspaper reporting. She concludes that she cannot claim his innocence, but the charge was never proved. Her account also records that Prestigiacomo's eight-year-old daughter Frances testified at the coroner's inquest that Aiello had asked her to call a cab.
Nobody was convicted. None of the accounts cited in this article identifies the shooters or the person who ordered the killing.
Weighing the case against Capone
The accusation against Capone's organization rests on motive and method, not on proven acts.
What supports it:
- Aiello was a long-standing, public enemy of Capone, with alleged plots against him going back to 1927.
- The ambush was meticulous: rented rooms, overlapping fields of fire, a third backup position, and a burned getaway car.
- Police, prosecutors and federal agents publicly speculated about Capone from the start.
- TIME noted that with Aiello gone Capone was left the "Biggest Shot of All."
What limits it:
- No shooter was identified, charged or convicted.
- Moran and outside Mafia forces appear in contemporary or later speculation.
- The Prestigiacomo accessory theory was never proven.
- Investigators in Chicago in this period were widely seen as unable or unwilling to build such cases, so the absence of a prosecution is not evidence of innocence either.
What Aiello's death changed, and what remains uncertain
Aiello's death removed one of Capone's two most prominent rivals. TIME wrote that, at the beginning of that week, three live leaders of Chicago gangland remained, Capone, Aiello and Moran, and by the end Moran was "a gangless gangster." Wikipedia says the killing left Capone effectively unchallenged in his control of Chicago. That is an interpretation of aftermath, not proof of who ordered the murder, and violence did not stop.
Wikipedia cites a Tribune report that a Capone-linked machine-gun nest was found opposite the home of four of Aiello's former henchmen a month later. It also cites the fatal shooting of Aiello's nephew Frank Aiello Jr. in Milwaukee in May 1931, which authorities believed was tied to the Chicago feud although the nephew had no apparent ties to organized crime.
Aiello's funeral on October 29 drew a crowd of more than 1,000 to Lunt and Rockwell, and an $11,000 casket left his home en route to Mount Carmel Cemetery, according to the historical society. His wife later moved his body to Rochester, New York, where she lived until her death in 1992.
The case also needs context. A study indexed by the U.S. Office of Justice Programs, by John J. Binder and Mars Eghigian Jr., counts 729 gangland-style killings in Cook County from 1919 to 1933 using Chicago Crime Commission and police records.
It found that 43 percent were unrelated to organized crime and only 40 percent were tied to bootlegging. Those figures put gang killings in perspective but say nothing about who killed Aiello.
What survives is a well-documented ambush, a feud with plausible suspects, and a prosecution that went nowhere.
Key dates in the Aiello-Capone conflict
| Date | Event | Responsibility |
|---|---|---|
| 1926 | Aiello and Tony Lombardo split; Lombardo aligns with Capone | n/a |
| May 1927 and Jan. 1928 | Gunmen attack the Aiello Brothers bakery on Division Street | Unknown |
| Sept. 7, 1928 | Lombardo shot at Madison and Dearborn | Aiello and allies suspected; no charges; never proven |
| Jan. 1929 (reported as Jan. 7 or 8) | Pasqualino Lolordo shot in his home | Early reports named Aiello; later disputed; unresolved |
| Apr. 24, 1930 | Chicago Crime Commission names Aiello among 28 public enemies | Official designation |
| Aug. 21, 1930 | Police raid Aiello's West Ridge home | Police action |
| Oct. 23, 1930 | Aiello shot at 205 N. Kolmar Ave. | Capone's organization suspected; no one convicted |
Frequently asked questions
When and where was Joe Aiello killed?
On October 23, 1930, at about 8:30 p.m., outside 205 North Kolmar Avenue on Chicago's West Side. He was shot from rented rooms across the street and in a neighboring building as he left to get in a taxi.
Was Al Capone proven to have ordered the murder?
No. Police and prosecutors suspected him immediately, and the style of the ambush fit earlier attacks attributed to him. But no court established responsibility, and other possibilities appeared in reporting at the time and in later histories.
Was anyone convicted?
No. Prestigiacomo, the host who sheltered Aiello, and an Aiello company employee were charged as accessories before the fact. The case went to a grand jury and was dropped.
Why were Aiello and Capone enemies?
They fought over control of the Unione Siciliana and the bootlegging that flowed through the Sicilian community. Aiello's former partner Lombardo sided with Capone, while Aiello allied with Capone's North Side rivals, including Bugs Moran.
How many bullets hit him?
Accounts differ. They range from 35 steel-coated bullets in the Tribune excerpt to 57 or 59 in later reports. Treat all the counts as approximate.
References
- 2012 Best of the Net Anthology — sundresspublications.com
- Joe Aiello — Wikipedia
- CRIME: One Big Shot — time.com
- Joe Aiello: Chicago’s “Tony Soprano” of the Roaring Twenties — Rogers Park/West Ridge Historical Society
- Rick Porrello's - AmericanMafia.com - Allan May, Organized Crime Historian and Journalist — americanmafia.com
- Gangland Killings in Chicago, 1919-1933 — Office of Justice Programs
