Tony D'Andrea Assassinated

Tony D’Andrea got his start in the dark corners and alleys of the Levee. Through hard work, muscle, and not a little violence, he rose to become Chicago’s leading Italian politician. He met his end in the bloodiest political feud in the city’s history, shot to death on the front steps of his home here at 902 S. Ashland Ave.

Born in Sicily in 1872, D’Andrea showed an early gift for languages, and graduated at the University of Palermo before making his way to the United States in 1896. He disembarked at Buffalo, New York, then found his way down to Baltimore, where he entered St. Mary’s Academy, a seminary where he trained for the priesthood. After three years at St. Mary’s, and with additional training at St. Bonaventura’s Academy in Allegheny, Pennsylvania, D’Andrea was appointed to a pastorship at St. Anthony’s Italian Catholic Church on the far south side of Chicago in June, 1899.

The clerical collar fit poorly. Six weeks after his appointment, D’Andrea fell in love with a woman, Lena Wagner, who he met in the barbershop of a friend on W. Grand Ave. The two eloped to Milwaukee and married there. D’Andrea was subsequently excommunicated from the church, and maintained a distant relationship to Roman Catholicism throughout the rest of his life. At his death, he was refused a church funeral.

(Pictured: Antonio D'Andrea, dressed in clerical uniform in 1899)

After leaving the priesthood, D’Andrea became a private language tutor, and also held part ownership in a macaroni factory in a warehouse district on the South side. To be close to the factory, he settled with his new wife in an apartment at 2125 S. Archer Ave., in what is today Chinatown. At the time, Mayor Carter Harrison was leading a political attack on the old Custom House Place red light district, and so this formerly-quiet neighborhood where the D’Andreas lived was quickly growing into the city’s premier red light district, soon to be known throughout the world as “the Levee”.

Around the same time, another couple, future mob-founder Jim Colosimo and his young wife Victoria Moresco, opened the New Brighton brothel just a block north on Archer Ave., and the Everleigh Sisters opened their famed house of ill-repute a block north of that. Criminal enterprise surrounded the D’Andreas, and the underworld opportunities were endless.

While vice was the preferred get-rich-quick scheme for those around him, D’Andrea’s religious leanings may have disinclined him from such pursuits. Instead, he took up counterfeiting.

Around 1900, D’Andrea traveled to New York, and there purchased a large quantity of phony dimes. It’s a testament to subsequent inflation that counterfeiting such small currency could have been profitable, but at the time, a dime could buy two “tubs” of beer at Michael Kenna’s Workingmen’s Exchange saloon.

The Secret Service, today best known for their work protecting the President, was originally established as an agency of the Treasury Department, tasked with investigating counterfeiters. In 1902, Capt. Thomas I. Porter of the Secret Service literally “followed the money” directly to a macaroni factory on the south side of Chicago, where he went undercover as a state tax agent to gain D’Andrea’s confidence. After he had collected sufficient evidence to prosecute, a squad of Secret Service agents and Chicago police arrived at the D’Andrea home on Archer with arrest warrants. While Mr. D’Andrea was being taken into custody, Mrs. D’Andrea, looking a little fuller-figured than usual, attempted to leave the house through the back exit. Captain Porter commanded an officer to stop her, at which point a bag full of counterfeit specie fell out from under her dress and scattered across the floor. The jig was up.

D’Andrea had little choice but to plead guilty, and federal prosecutors offered a deal by which he could avoid jail in return for turning state’s witness against the men who sold him the counterfeits. D’Andrea was taken to New York state to testify at their trial, but upon arrival, he refused to testify. Likely word had gotten to him that his life was in danger if he opened his mouth on the stand. Without D’Andrea’s testimony, that case failed, and the deal to save him from prison was off. In April, 1903, Antonio D’Andrea entered Joliet prison (the federal government at the time frequently placed criminals in state facilities), where he served 13 months.

It is an indication that D’Andrea already had powerful friends in the Chicago Italian community that, at the end of his prison sentence, he received a “civil pardon” from President Theodore Roosevelt, which restored his civil rights, though it did not clear his record or spare him from serving any of his time.

There is some evidence that, after release, D’Andrea continued activity in the counterfeit money racket for some time, but he certainly continued building his language tutor and macaroni-production businesses, both of which were successful. He was also able to help his Sicilian family come to Chicago, and several of his brothers and nephews also became successful. His brother Joseph D’Andrea became involved in organized labor, and rose to become president of Sewer and Tunnel Miners’ Union Local #4. In those days, as today, there were severe battles between unions, frequently organized along ethnic lines, for major work contracts. Joseph D’Andrea was involved in just such a struggle over the West Side site where Union Station was then under construction, and he was shot and killed there under mysterious circumstances in the fall of 1914.

He may have been the victim of some agent of a rival union, or his death may have been from a disgruntled member of his own union. Joseph D’Andrea had organized a system by which laborers had to pay $5 in dues to the union every time they took a new job; given the level of turnover in the construction industry, this was a frequent occurrence, and a source of some bitterness among the rank-and-file. In any case, upon his death, his brother, now going by the Americanized name “Anthony” to distinguish himself from his former life as “Antonio”, took over the presidency of the largely Italian union, a position he used to propel himself into politics. Through his work with the union, he also became close friends with “Diamond Joe” Esposito, who was working as a business agent for the sewer and tunnel miners, and who would one day also become an important political and underworld figure in Chicago.

By this time, Tony D’Andrea and his wife had moved from the Levee district into the Little Italy neighborhood, located in the 19th ward, taking up residence at 745 S. Halsted St. In 1914, he first dipped his toe into Chicago politics, running for county commissioner as a Democrat. Though he lost the race, his was clearly a political star on the rise. The following year, he was appointed the ward leader for Democrat Robert Sweitzer's 1915 mayoral campaign. In a bruising primary against the incumbent, Carter Harrison, Sweitzer emerged victorious, with a large margin of victory among Italian voters in the 19th ward. Sweitzer was ultimately defeated in the general election by Republican William Hale Thompson (the last Republican mayor of Chicago), but 19th ward alderman John “Johnny De Pow” Powers, who had led the Harrison campaign in the ward, began to see D’Andrea as an important political rival.

Powers, an Irishman representing an increasingly Italian constituency, was an astute tactician, and offered his support to D’Andrea for various political offices (other than alderman), including county commissioner. But the ex-priest had his eyes on a bigger prize, and in 1916, he ran for alderman from the 19th ward. In those days, each ward had two aldermen, with staggered terms. In 1916, Powers’ acolyte in the 19th, James Bowler, was up for re-election, and the Democratic primary battle between Bowler and D’Andrea promised to be fierce. Bowler had Ald. Powers on his side, and D’Andrea was supported by Rocco de Stefano, a close confidant of vice-magnate and Levee heavyweight “Big Jim” Colosimo.

February, 1916 found D’Andrea courting votes among the ward’s residents. In one case, he volunteered to be a character witness in court for a fellow Sicilian who was seeking naturalization. When the Superior Court clerk sought to verify D’Andrea’s own citizenship, however, he looked under “D” instead of “A”, and when he found nothing in the state’s records, suspicions began to circulate that the aldermanic candidate was not a U.S. citizen. This led others to dig into D’Andrea’s past, where they uncovered the case of a very similar-looking man, also named D’Andrea, an defrocked priest who had served 13 months at Joliet for counterfeiting.

The news hit the papers, and Ald. Bowler hired Pinkerton detectives to investigate D’Andrea’s past. They quickly surmised that Anthony D’Andrea, the labor leader and pillar of the Italian community, and Antonio D’Andrea, the passer of phony dimes, were one and the same man. Speaking to reporters the next day, D’Andrea admitted as much, but offered a stirring – if not quite believable – defense:

The facts were that when a counterfeiter was trailed by the government official to my house and placed some counterfeit money in our pantry during my absence, Mrs. D’Andrea, a most lovable and charitable woman, in order to remove the stain of suspicion from the sacredness of her own home and family, discovered that in some inconceivable manner the money was hidden in her pantry, took it out for the purpose of reporting her findings to me, and to remove the odium of guilt from my happy and cheerful home.

In the meantime, as she was about to leave the house, the government officials arrested her and kept her in custody for many hours, before I was allowed to see my wife, who had already become a human wreck from anguish, sorrow, and disgrace. With the most profound love for her and with the hope that not a stain should be placed against her character nor the character of our little girl, and with the promise that if I took the blame, my wife would be liberated, under the most inscrutable circumstances that could be imagined, and with the promise that if I gave to the government officials information regarding the gang of counterfeiters and plotters that I would be released, I remained silent, so as to shield them who had already threatened my life and that of my family if I spoke.

As a result of which I was forced to keep within my bosom the secret which, if exposed, would mean my immediate death, and I became a victim of the most unparalleled conviction that was ever had in the federal court.

At the time, it was pointed out that an Illinois statute forbade anyone convicted of a felony of holding public office, but D’Andrea’s civil pardon from Pres. Roosevelt apparently allowed him to remain in the race, though he was now scandal-ridden. Essentially the only quality that recommended D’Andrea to the office was the fact that he was an Italian, running in a ward that was, by this time, almost 80% Italian residents.

Thus, D’Andrea and his supporters took it personally when some of their fellow countrymen failed to support him. And some of D’Andrea’s supporters were rather violent men, including the Genna family, who in a few years would spill innumerable gallons of blood while running the city’s bootleg distillery business. On the evening of February 21, 1916, Frank Lombardi, an Italian immigrant and a major supporter of Ald. Bowler, was in the saloon he ran on Taylor street when two friends arrived. The three men raised their glasses in a toast, and at that moment, one of Lombardi’s “friends” pulled a revolver and shot him in the gut, an injury he eventually died from.

Lombardi’s death further cast the pallor of the underworld over D’Andrea’s candidacy, and on March 1, with the votes counted, James Bowler defeated Anthony D’Andrea, 4,163 votes to 1,753. D’Andrea was disappointed, but he had only just begun to fight. There would be many more opportunities to come.

D’Andrea focused on continuing to build support among the ward’s Italian residents, making his headquarters on Taylor Street the “Italian-American Educational Club”. He also became president of the Unione Siciliana, the chief social and political organization of Sicilians in Chicago; future leaders of the organization include such criminal luminaries as Angelo Genna, Sam “Samoots” Amatuna, Antonio Lombardo, and Joe Aiello. D’Andrea’s business and political success is reflected in the fact that he was able to purchase a large home at 902 S. Ashland Ave., where he lived with his wife on the second floor, and rented out the first floor.

In 1919, D’Andrea ran to be a delegate to a constitutional convention in Illinois to be held in 1920. When the votes were counted, the official record on the night of the election showed D’Andrea had lost by 82 votes; however, a later recount showed D’Andrea the victor. A court inquiry into the election turned up substantial evidence of fraud, with many of the additional so-called “voters” having not actually voted, or in the great Chicago tradition, having died years earlier. The extra votes were thrown out, and D’Andrea was again the loser.

Nevertheless, D’Andrea was still considered an important political figure in the district. So much so, in fact, that in order to dissuade him from running for alderman against him in 1921, Ald. Powers supported D’Andrea for the position of ward committeeman, a position that held at least as much, if not more, power than the aldermanship itself. In April, 1920, with Powers’ help, D’Andrea was elected to the position; however, voter irregularities again sandbagged the count, and a court threw out the results.

At this point, as described in this post, Ald. Powers dramatically recanted his support for D’Andrea, and chose to fill the ward committeeman position himself. Soon after, Powers’ home was the target of a bombing. As the incident suggests, D’Andrea and his supporters were increasingly turning from away from the ballot and towards violence. In 1921 D’Andrea announced he would run against Powers in the next aldermanic election, and the campaign between the two was the bloodiest in Chicago history, with dirty tricks and intimidation on both sides.

In February, a bomb exploded outside a D’Andrea rally near Blue Island and Taylor. When reporters approached D’Andrea, he practically admitted a role in the earlier bombing of Powers’ home:

I wouldn’t care if they threw a bomb at my house. That’s all in the game, and it wouldn’t hurt any one else but me. But to throw one into a meeting where there are a lot of workingmen, that’s another thing.

In retaliation for the bombing, D’Andrea’s supporters, which likely included the wildest of the Genna clan, Angelo Genna, and Sam Amatuna, organized a violent hit on two Italian precinct captains for Powers, as described in this post. Election day was a complete fiasco, with kidnappings of election workers, and widespread violence and intimidation of voters, but at the end of the day, the old “gray wolf,” John Powers had defeated his rival by the narrow margin of 381 votes.

With another lost election, D’Andrea declared “I’m through with Nineteenth Ward politics for good.” Asked for comment, Ald. Powers sarcastically replied, “Very magnanimous of him, I’m sure.”

But D’Andrea’s word was accurate. His political life was at an end – if only because the rest of his life was, too. D’Andrea had taken to carrying a pistol with him everywhere, and had been arrested for carrying a concealed weapon on several occasions; the violence associated with the election had likely warned him he was a marked man.

On the evening of May 10, 1921, he was out late, enjoying dinner with his old friend and political compatriot, “Diamond Joe” Esposito, at a local Italian restaurant. At 2:00 a.m., his bodyguard and driver, Joseph Laspisa, dropped him off in front of his home at 902 S. Ashland, and sped off, while D’Andrea climbed the stairs to his second-floor apartment. The first floor apartment was empty at the time, though the D’Andreas had hired decorators to paint and refurnish the flat for rental. The previous residents of the first floor had left at the beginning of the month, after receiving a threatening note, indicating that D’Andrea’s rivals were planning to dynamite the building.

In any case, the first floor apartment was unoccupied, but there had been some activity there all afternoon, which the neighbors attributed to the decorators. But no decorators had been on the site that day. As D’Andrea climbed the steps of his building, a sawed-off shotgun peaked through the window from the first floor, and fired off seven shots, five of which hit their mark. D’Andrea reached for his pistol and fired back, but quickly collapsed on the steps as his assassin escaped out the back and into a waiting car in the alley. Hearing the shots, Mrs. D’Andrea arose from bed and hurried down to where her wounded husband lay. “Lena, Lena, I’m dying, I’m dying,” he cried out to the woman he had left the church for.

(Pictured: Illustration of D'Andrea's home on S. Ashland Ave., where he was shot)

When police arrived, they found two clues in the first-floor apartment assassins’ nest: a soft brown hat, size 7, with the initials “S.P.” inscribed inside, and a $20 bill in the hat band, along with a card reading “For Flowers”. Police also found a handprint in some freshly laid paint, presumably left by the killer.

Suspicions immediately turned to Ald. Powers and his supporters, although Powers disowned the killing: “I do not believe it was politics. D’Andrea has had a good deal of trouble and it hasn’t been all political. He has been mixed up in labor matters and there may be some race feud back of it.”

Asked for comment, “Diamond Joe” Esposito, D’Andrea’s dinner companion that night and also a political figure in the ward simply responded, “So they shot him, eh?” Political violence had made killings in the 19th a fact of life.

D’Andrea hung on to life for a few days in the hospital, but finally succumbed on May 12. Refused a church burial due to his excommunication in 1899, a service was held on the steps of his home on Ashland Ave., right where he was shot, and 8,000 attended, flooding the street with people for three blocks around.

The bloodletting in the 19th did not, however, end with D’Andrea’s death. Ten days later, Michael Licari, a D’Andrea partisan, was murdered, and the following month, Joseph Laspisa, D’Andrea’s bodyguard and his driver on the night of his death, was killed while driving down Oak St. in Little Sicily, near "Death Corner", shot by a back seat passenger. Eventually, over 30 murders were attributed to the Powers/D’Andrea fight, most of them, including D'Andrea's, never solved.

The dream of an Italian alderman to represent Little Italy also died with D’Andrea that night. In July, 1921, with pressure from Ald. Powers, the 19th ward was redrawn and broken up into parts of the 20th, 25th, 26th, and 27th wards, none of which had an Italian majority.

After his death, the Genna brothers took over D’Andrea’s political headquarters and turned his political bailiwick into the massively dispersed distilling organization that supplied a large portion of the illegal liquor in Chicago during Prohibition. Several of D’Andrea’s relatives were closely involved with the Gennas and their partners in bootlegging, the Torrio-Capone organization. One nephew, also named Anthony D’Andrea, was Capone’s manager for his Depression-era soup kitchen on S. State st. Later, he became the president of the powerful hod-carriers union, and was a defendant in a federal antitrust case in the 1940s, accused of restraining the use of ready-mix concrete in Chicago, which would have eliminated a large number of union jobs.

Another nephew, Philip D’Andrea, got his start as a bodyguard for Al Capone, and was later a key member of The Outfit, the mob organization constituted of Capone’s men, after Capone went to prison in 1931. Philip D’Andrea served three years in prison in the 1940s on charges of extortion, along with Outfit luminaries Paul “The Waiter” Ricca, Louis “Little New York” Campagna, and Charles “Cherry Nose” Gioe.

D’Andrea’s home at 902 S. Ashland stood into the 1980s, when it was demolished to make way for the University of Illinois at Chicago’s Molecular Biology Research Building, completed in 1995. The building is notable for a large staircase inside that mirrors the shape of a double helix.

Death in the Barber's Chair: The Rise and Fall of Sam Amatuna

Unione Siciliana president Mike Merlo had kept the peace between rival alcohol-production organizations in Prohibition-era Chicago through his death in 1924. Over the next year, the violent war between the “Bloody” Genna brothers, operators of a gigantic dispersed distilling operation in Little Italy, and the Northside Gang headed by Dion O’Banion, heated up, and news of assassinations filled the city’s newspapers. Into this tinderbox stepped the dapper Don of the Maxwell Street district, Salvatore Samuzzo Amatuna (frequently known as Sam or even “Samoots”). As head of the powerful Unione, the young Amatuna struck a pose as a political kingmaker and gadabout in the Sicilian community, but he couldn’t bring peace to the underworld, and the bloody beer wars escalated until they claimed Amatuna himself as a victim, as he sat in a barbershop here, at 804 W. Roosevelt Rd.

Amatuna was born in the seafaring town of Pozzallo, Sicily, at the far south end of that island, in 1899. As a teenager, he found his way to Chicago, settling in the “Little Italy” district along Maxwell Street in the early 1910s. Like many young Sicilians in the neighborhood at the time, he found his calling in politics, providing the street-level muscle in the increasingly violent war over the aldermanic seat in the 19th ward, which included Little Italy. John Powers had held the seat since 1888, when the 19th was predominantly populated by Irish, but by the 1910s, Powers was presiding over an increasingly-Italian ward, and the new immigrants had their own rising political stars, including “Diamond Joe” Esposito and former Roman Catholic priest and convicted counterfeiter, Anthony D’Andrea.

D’Andrea ran against Powers’ right-hand man, James Bowler in the aldermanic election of 1916 (in those days, each ward had two aldermen), and the race was close, despite pre-election revelations about D’Andrea’s criminal past. Not all Italians in the 19th supported D’Andrea, however; Powers had made a career out of incorporating potential Italian rivals into his organization over the years. In fact, one of Bowler’s chief political advisors was a Sicilian, Frank Lombardi.

Nothing irked D’Andrea’s supporters more than the defection of Lombardi and other fellow countrymen – Italians constituted a substantial majority in the ward by that time, and easily could have elected one of their own, had they united behind D’Andrea. Just days before the election, Lombardi met two friends in a saloon on Taylor street. As the trio raised their glasses in a traditional Sicilian toast, one of the “friends” drew a .38 caliber revolver from his hip pocket and shot Lombardi dead.

The police advanced the theory that Lombardi was the victim of a “Black Hand” extortion scheme, a common occurrence among well-heeled Italians of the era, but Lombardi’s wife and just about everyone else blamed supporters of D’Andrea. The accusations among those in the know in Little Italy led directly to a hot-headed 17-year old from Sicily, Sam Amatuna.
Amatuna was questioned in Lombardi’s death, but with little evidence and most eyewitnesses unable to “remember” the scene accurately, no charges were ever filed. The murder may even have been counterproductive, as it revived voters’ recollections of D’Andrea’s sordid past, and
James Bowler won the election of 1916.

Regardless of his real guilt or innocence, Amatuna’s reputation as a man to be feared on Maxwell Street was established. Through his connections in D’Andrea’s organization, he also became a close ally of the Genna brothers, especially the toughest and most violent of that clan, Angelo. Both Angelo Genna and Sam Amatuna were fearsome characters in the district, but unlike Genna, Amatuna was able to separate business from social concerns, and when not cracking skulls for D’Andrea, he was widely known for his generosity and sunny personality, even gaining the moniker of “Smilin’ Sammy Samoots” in some quarters.

But behind the smile remained a man talented with a gun, and one fearless in using it for his own advancement. As one friend told reporters later, "Sure, if he wanted a guy knocked off, he'd have him knocked off, 'what the hell?' But he was a good guy just the same."

(Pictured: Sam "Samoots" Amatuna)

In 1921, D’Andrea again ran for alderman, this time directly challenging the incumbent Powers. Once again, D’Andrea relied on the force and violence doled out by toughs like Amatuna to help get out the vote, and once again, Italians supporting Powers were a major target (for his part, Powers was never afraid of dirty political tricks either). During May of that year, Paul Labriola and Harry Raimondi, lieutenants in the Powers organization, both met their ends at the hands of a five-man assassin crew, widely believed to have been headed by Angelo Genna and Sam Amatuna. Genna was arrested and put on trial, but walked when the prosecution’s lead witness changed his story on the last day before the jury convened.

Again, D’Andrea was unable to capture a seat on the city council, losing the election by 435 votes. Shortly after the election, D’Andrea was murdered, and the Genna brothers took over his organization, turning it from a political enterprise to a criminal one. With their base of Sicilian supporters, they produced massive quantities of (rot-gut) liquor in small stills in basement apartments throughout Little Italy, in the process becoming the key part in the supply chain that ended in the blind pigs and speakeasies run by Johnny Torrio and Al Capone. The Gennas employed Amatuna as the enforcer for their network of family-run microbreweries. It was “Smilin’ Sammy” who visited those who failed to meet their promised quotas of booze, and few suppliers fell behind the production schedule twice.

Violent and superstitious, the Gennas began butting heads with rival booze gangs, especially the Northside gang, run by the equally-superstitious singing-waiter-turned-florist, Dion O’Banion. O’Banion’s reckless hijacking of Genna deliveries, plus his general disrespect for his Italian competitors, made the blood of Angelo Genna and Sam Amatuna boil. The only factor keeping O’Banion from meeting the same fate as Lombardi, Labriola, and Raimondi, was the word of Mike Merlo, chief of the most powerful Sicilian social and political organization in the city, the Unione Siciliana.

But Merlo’s days were numbered. In 1924, he died of natural causes, and a few days later, O’Banion was dead in his floral shop, shot dead by three men, believed to include the Gennas' masterful assassins Scalisi and Anselmi, plus a third man, who the police believed to be either Angelo Genna or New York-based Unione president, Frankie Yale. When the police brought Yale in for questioning, it was Sam Amatuna who provided an alibi – Amatuna and Yale had been dining at the Palmer House hotel at the time, he claimed. No one was ever charged with the crime.

With the mediating influence of Merlo gone, the bullets flew in Chicago, and in the coming months, three Genna brothers met the same fate as O’Banion. Johnny Torrio was nearly assassinated as well, and he and the remaining Gennas fled the city.

Into the consequent void of power in Little Italy stepped Sam Amatuna. After Angelo’s death, he took two bodyguards and walked into the headquarters of the Unione Siciliana, informing everyone that he was now president. In his attempt at changing from a mere street tough to a powerful political force, he began acting the part of neighborhood Don, dressing in snappy clothes (it was said he owned 200 embroidered silk shirts – the newspapers repeatedly referred to him as the “Beau Brummel of Little Italy”) and buying haircuts and shaves for the teenagers hanging around the barbershop whenever he went in for a trim.

But make no mistake – under the silk shirt beat the cold heart of a killer. A story frequently passed around about Amatuna said that when a certain dry cleaners damaged his clothes, the enraged dandy retaliated by ripping out the stairs connecting the laundry from the street, and put a bullet through the head of the proprietor’s horse.

With the wealth he had amassed from his work with the Gennas, Sam Amatnua purchased a jazz club, the Bluebird Cafe, at Halsted and Taylor, for $40,0000, where he himself often performed, gaining a reputation as an excellent singer and violinist. He also acquired a beautiful home on Lexington Ave., near Damen Ave. (the street has since been vacated in that block). And most important of all, he was engaged to wed Miss Rose Pecaroro, sister to Mike Merlo’s widow. The marriage would make Amatuna peerless as a Sicilian community leader.

It was on a visit to the barber that Sam Amatuna met his end. On the evening of November 11, 1925, Amatuna walked into his favorite local barbershop at 804 W. Roosevelt Rd. He and Pecaroro were to see the opera Aida at 8:00 that evening at the Auditorium building on S. Michigan Ave. Isidor Paul, who had owned and operated the barbershop since 1918, threw a hot towel over Amatuna’s face and sharpened his razor. By coincidence, Amatuna was without his usual bodyguards that evening, and as a show of power, he never carried a gun personally any more.

At that moment, two olive-skinned men, one short and one tall, walked into the shop and drew guns. Paul screamed, and Amatuna jumped out of the barber’s chair, hiding behind it. The Tribune describes what happened next:

Two men walked in as he left the chair in which he had been shaved and massaged in preparation for an evening at the opera, and without waiting opened fire. Eight times their weapons cracked. One bullet took effect and Amatuna dropped: the others went wild as barbers and customers fell to the floor or ran for cover. Then the attackers backed out, ran to a car parked at the curb and escaped.

Two friends helped the bleeding Amatuna into a taxicab. Their first destination was not the hospital, but a cigar shop owned by Amatuna, around the corner at Taylor and Halsted Streets. There, Amatuna briefly met with his brother, Luigi, who had recently arrived from Sicily, likely informing him of the names of his attackers. From there, the trio left for the hospital.

For two days, doctors at Jefferson Park Hospital tried to revive Amatuna, but to no avail. With her planned elaborate wedding just weeks away, his bride was doubly stricken, and Amatuna agreed to a bedside ceremony in case he was unable to recover. With the physicians’ negative prognoses in mind, a priest was called and the arrangements made for just such an event. But before the ceremony could take place, Amatuna fell unconscious, and died at 2:00 a.m. on November 13.

As was customary for gangsters in his time, Amatuna’s funeral was lavish. At his fiancée, Rose Pecaroro’s home on the North side, $20,000 in flowers filled the home, the yard, and several neighbor’s yards. The casket was made of silver and cost a reputed $10,000. The funeral procession to Mt. Carmel cemetery, where Amatuna’s body was held in a vault for several days before being shipped back to Sicily, stretched for over a mile, snaking through the city past his home, his businesses, and stopping at the barbershop where he died – a visible indication of future retribution. At the gravesite, Luigi Amatuna threw himself on the coffin, beating his fists on it and swearing an oath of revenge in his native tongue.

(Pictured: The scene outside Amatuna fiancee, Rose Pecaroro's home, where Amatuna's funeral procession began)

Indeed, the bloodshed was far from over. Within a week, both of Amatuna’s absent bodyguards were killed – one of them on the way home from the funeral ceremony. Next in line for the presidency of the Unione Siciliana was Tony Lombardo, Al Capone’s personal friend. Lombardo was assassinated in the middle of the day at Madison and Dearborn Streets in the loop. The three succeeding Unione presidents, Pasqualino Lolordo, Joseph Giunta, and Joe Aiello met similar fates. The bloodshed of the 1920s sealed Chicago’s worldwide reputation as the country’s crime capital.

Who killed “Samoots”? The chief theory is that his death was merely another part of the spiraling bloodshed between the Genna-Torrio-Capone organization and the Northside gang. Most historians believe that Amatuna’s assassins were Vincent “Schemer” Drucci, one of the leaders of the Northside group, and Jim Doherty, a key member of the allied Westside O’Donnell gang. It appears Al Capone blamed Drucci and Doherty. A few months later, when Doherty and Assistant State’s Attorney William McSwiggin were seen drinking and gambling in Cicero at the Pony Inn, Capone ordered a hit on crew, in which McSwiggin died, a major factor in turning public opinion against Capone and raising his profile with Chicago police.

An plausibly, though less likely alternative theory is that Amatuna had fallen out with the Gennas in the months before his death, and that Capone ordered his murder in order to make way for his friend, Lombardo, to control the Unione and the Genna distillery network. In Chicago’s gangland, today’s allies frequently became tomorrow’s enemies, and vice-versa.

The barbershop where Amatuna met his fate continued in operation, run by Isidor Paul, until his retirement in 1956. Today, like much of the old Little Italy neighborhood, the building is gone, razed to make way for the facilities of the University of Illinois at Chicago. Until recently, the site was a baseball field for the UIC team, but is currently marked for the construction of a new condominium complex, Roosevelt Square.

Aiello & Co. Bakery

Joe Aiello had broken troth with his former business partner, Antonio Lombardo, and was actively scheming to kill Lombardo and his colleague in crime, Al Capone. On May, 28, 1927, Aiello’s bakery, located here at 473 W. Division St., took the brunt of Lombardo and Capone’s ire when it was riddled with over 200 machine gun bullets from in a gangland drive-by shooting.

Giuseppe Aiello, known as “Joe”, was born in 1890 in Sicily, into a very large family. Most accounts claim he was the oldest of seven brothers, but others indicate up to ten Aiello brothers, plus an unknown number of cousins, uncles, and nephews. Most of the family emigrated to the United States in the first decade of the 1900s, including Joe, who arrived at New York in 1907, then moved west to Chicago shortly after.

Food was the family business, and Joe operated first as a cheese-maker and grocer in the Little Sicily enclave on the near North side (also known as “Little Hell” for the poverty and violence that infested its streets). With his brothers, he also opened a wholesale bakery specializing in supersized wedding cakes and Italian breads, Aiello & Co., at 473 W. Division, near the corner of Clybourn Ave. He also held part ownership in a candy shop near Oak St. and Cleveland Ave. (then known as Milton St.), the original “Death Corner,” a popular Black Hand meeting (and “disposal”) ground.

At the onset of the 1920s, the Aiello clan was already prominent in the Sicilian-American community. National alcohol prohibition raised their profile further. During Prohibition, grocers played a particularly important role in the production of bootleg alcohol, since they could purchase and store large quantities of important distilling ingredients, such as sugar and grapes, without arousing the suspicions of police. Joe Aiello used his position as one of the neighborhood’s top grocers to become deeply involved in the business of illicit booze.

He joined forces with another prominent Sicilian grocer, Antonio Lombardo, and the two opened an import business on Randolph Street and purchased property on the west side at Kinzie and Halsted for an even larger operation. At the time, Lombardo was also president of the Unione Siciliana, the primary Italian organization in Chicago, a position that made him the most respected man in the immigrant community, and a political “fixer” with connections in city government and law enforcement. The Unione was a key element in organizing the massive, dispersed network of tiny home distilleries that supplied the low-quality liquor that was eventually retailed through Al Capone’s syndicate.

(Pictured: Giuseppe "Joe" Aiello)

Together with Lombardo and Capone, Joe Aiello ruled Chicago’s illegal alcohol trade into early 1926. The decline and fall of their fellow Sicilian booze entrepreneurs, the “Terrible Genna” brothers, in 1925 gave Aiello and Lombardo an even more important role to play in this business. But Aiello was too ambitious to be just one important part of the machine. He needed to control it all. He was especially jealous of Lombardo’s position at the Unione and the respect it earned him among their countrymen. And he despised Capone, a non-Sicilian he considered untrustworthy and undeserving of his wealth. Aiello’s constant attempts to control more of the alcohol syndicate eventually led to a break with Lombardo in 1926, and an all-out war for the control of the Unione and the Little Sicily neighborhood.

Aiello began working closely with the Northside Gang run by George “Bugs” Moran and Jack Zuta, while Lombardo remained close with Capone. Both Lombardo and Aiello keenly courted Sicilian grocers, demanding their loyalty and supply capacity. For his part, Aiello openly put price tags on the heads of Lombardo and Capone, offering up to $50,000 each to a series of hitmen in return for their lives.

In one important case, Aiello made a $35,000 deal with a cook at the “Little Italy” restaurant, located at 22nd and Cicero Ave., in the suburb of Cicero, to spice Capone and Lombardo’s soup bowls with prussic acid. The cook wisely decided against fulfilling the task and confessed the deal to Capone.

Other Aiello family members were also involved in warfare with Capone and Lombardo. Tony Aiello, Joe’s brother, was positively identified by a boy eyewitness as the murderer of Antonio “The Cavalier” Spano, a Capone associate operating out of Chicago Heights, who met his end just a block away from the Aiello brothers’ bakery on Division St. Tony managed to beat the rap despite the witness’ identification.

(Pictured: Tony Aiello)

Joe Aiello also attempted to hijack the Unione from outside, sending a gaggle of his brothers and nephews to St. Louis in an attempt to build a rival organization that he could eventually bring to Chicago. Their attempts to consolidate power in that city led to a dozen murders in 1927, including the deaths of two Aiello brothers while sitting in a restaurant in Springfield, Illinois.

Lombardo and Capone realized that Aiello would stop at nothing to gain control of the Unione and the alcohol business in Chicago. On the evening of May 28, 1927, just after nightfall, a curtained touring car filled with four Capone gangsters cruised past the Aiello bakery on Division St., produced machine guns, and carpeted the building from side to side with a tremendous fusillade. By the end of it, over 200 bullets had lodged in the roof, floor, and walls.

At the time, Joe was in the bakery with his brothers, Dominic and Tony, along with two employees. Tony was hit in the neck, and dropped to the floor screaming “I’m dead,” while one of the employees was also shot in the side. Dominic and Joe were upstairs and managed to dodge
the bullets. As soon as their assailants departed, Joe and Dominic helped Tony out of the building and into surgery under the care of a friendly family physician (Tony survived). By the time the police arrived, only one employee remained in the bakery to tell the tale. Officers were unsurprised to find that Aiello & Co. was one of the city’s most well-armed cupcake retailers – a case filled with shotguns was discovered in a back room.

(Pictured: interior of the Aiello bakery, facing the mirrored back wall, which was shattered by bullets)

One Joseph Paglisia was arrested for the crime a few days later, as he was spotted driving through Little Sicily with a Florida license in a car similar to that from which the bombardment of the Aiello bakery had originated. It was a custom with the Capone organization for particularly spectacular hits to be performed by gunmen imported from outside Chicago. Nevertheless, the police were unable to find any further evidence against Paglisia, and he was released. No one else was ever fingered for the crime.

The attack at Aiello & Co. raised the stakes in the feud over the Unione, and that summer, nine Italian grocers were found dead, likely caught in the war between Aiello and Lombardo. Aiello also stepped up his attempts to kill Lombardo. Instead of attempting to procure a hit, he decided to organize one himself. Police discovered machine gun nests across the street from Lombardo’s home on W. Washington Blvd. (an event that caused Lombardo to move his family out to Cicero), and across the street from Michael “Hinky Dink” Kenna’s cigar shop on S. Clark St., a common meeting place for Capone and Lombardo.

In retaliation, Aiello and his Northside Gang allies saw bombs explode at several of the businesses, including a brothel located at Adams and Halsted – Capone territory – and a disorderly hotel at Madison and Western. The violence in the city produced by the feud in late 1927 was tremendous. The police organized roving groups of officers, armed with automatic weapons and with orders to kill on sight any known gangsters. Chief of Detectives William O’Connor (who took over that position after Michael Hughes was demoted for being too chummy with gangland figures), took an especially hard line on crime:

The machine gun is a much better weapon than the law to fight gangsters with. If we would hold more murder trials in the street rather than trust timorous juries to convict killers, Chicago would not now be facing a gang crisis.

1927 also saw Joe and Dominic Aiello build a beautiful new home for themselves and their wives, far from the Little Sicily slums where they grew up, in Rogers’ Park, overlooking Indian Boundary Park. That building, 2553 W. Lunt Ave., is still there, though it has since been
subdivided into flats.

(Pictured: 2553 W. Lunt Ave., as it stands today (above), and in 1930 (beneath). During the 1920s, this was the home of Joe and Dominic Aiello. The building appears to have changed little over the past 80 years, although the landscaping has improved).

In January, 1928, the Aiello bakery was again targeted. This time, it appears that Dominic was the target of an assassination plot. On the evening of Jan. 5, two men, armed with pistols and shotguns, walked into the building on W. Division, expecting to see Dominic at his usual post. In fact, Dominic had left the business at 4:00 that afternoon, but one of the bakers was still there, and began walking towards the door to greet them. Suddenly, the two opened fire, pouring all of their ammunition into the walls and ceiling, particularly the place where Dominic usually stood. They took no consideration of the baker, who was now cowering behind a glass case, though in full sight. Having emptied their guns, the men dropped their weapons and left the building as quickly as they had arrived. Likely they did not know that, while Dominic had left for the day, his wife, Grace, and their three children were just in the adjoining room. All escaped injury.

(Pictured: interior of the Aiello bakery after the Jan., 1928 shootout there. Arrows point to bullet holes in the walls and ceiling)

The summer of 1928 saw continued warfare between Aiello and Lombardo. In June, the bullet-riddled corpses of two Capone henchmen, John Oliveri and Joseph Salamone, were discovered at Death Corner, a half-block from the Aiello confectionary on Oak St. A month later, one of Aiello’s bodyguards, Anthony “Tough Tony” Califura, met his end in a drive-by shooting at North Ave. and Wells St. Four days later, an Aiello uncle was murdered in his Little Sicily grocery store, just south of Death Corner.

Finally, on September 7, 1928, Antonio Lombardo was murdered in broad daylight near the corner of Dearborn and Madison, in the full view of thousands of pedestrians. His killers escaped, but no one doubted that the Aiellos were behind the hit.

After the death of Lombardo, Joe Aiello saw an opportunity to finally gain control of the Unione Siciliana, but Capone and other allies managed to install Pasqualino Lolordo, a Lombardo associate, as president instead. To Joe Aiello, this simply meant one more bullet was needed, and in January, 1929, Lolordo was killed by three assailants while sharing drinks at his North Ave. apartment. At police headquarters, Mrs. Lolordo, who was preparing dinner in the adjoining kitchen at the time of the murder, was shown a photo lineup of potential assassins. She screamed when she saw Joe Aiello’s picture. While he was likely not one of the actual assassins (later evidence suggested the three assailants were Northside Gang members Frank and Peter Gusenberg, plus James Clark – all three later died in the St. Valentine’s Day Massacre), there was no doubt that Joe Aiello had organized the hit.

Finally, in 1929 and early 1930, most sources indicate that Joe Aiello finally did fulfill his long-time dream of becoming Unione Siciliana president. During this time, Al Capone was incarcerated in Philadelphia on weapons violations charges (he likely entered prison under his own volition as a way to protect himself from the spiraling violence on the streets of Chicago). For his part, Aiello spent much of his term as president hiding out in Northwest Indiana, a fugitive from police who wanted him for questioning regarding the Lolordo murder.

By late 1930, Aiello had returned to Chicago, but so had Capone, and old rivalries die hard. Joe Aiello was killed in an ambush on the far west side, near the Cicero border, on October 23 of that year. The rest of the Aiello family remained active in the underworld, eventually mending fences with the remnant of Capone’s organization, the Outfit, in the 1930s. In New York, the Aiellos are associated with the Bonanno organization, one of the “Five Families” in that city.

The old Aiello bakery remained in the family into the 1940s, serving as the headquarters for the San Giuseppi di Bagheria society, an Italian community organization focused on Bagherian immigrants (the locale in Sicily where the Aiellos originated). The building was destroyed in the early 1950s to make way for the Cabrini housing projects. In the 1990s, most of the major Cabrini-Green projects were razed, and replaced by upscale condominiums and mixed-income public housing. Where Aiello & Co. once baked wedding cakes and planned a takeover of Chicago’s bootlegging industry, a condominium building has recently been constructed.

Antonio Lombardo Killed in the Loop

In 1925, Antonio Lombardo became president of the Chicago chapter of the Unione Siciliana, a community and political organization of immigrants. In those days, the presidency of that organization was one of the most profitable -- and dangerous -- jobs in the world, and danger caught up with Lombardo on September 7, 1928 near the corner of Madison and Dearborn Streets in one of the most spectacular mob hits of all time.

Tony Lombardo was born in Sicily in 1891, and came to Chicago as a teenager. He built a successful grocery business as a young man, and in so doing, elevated his political profile in the impoverished neighborhoods of his countrymen, including Little Sicily/Little Hell on the north side and the 19th ward on the west side. Lombardo was an associate of the "Terrible" Genna family, which controlled the dispersed network of home distilleries, mostly operated by Sicilians, which supplied the Johnny Torrio – Al Capone syndicate with product during the Prohibition years. Lombardo's wholesale grocery had the lucrative position of supplying bulk sugar (one of the main ingredients in home “alky-cooking” for the Genna network.

(Pictured: Antonio Lombardo)

Lombardo’s partners in the grocery business included Joseph Ferraro and Joseph Aiello. Aiello, one of a large family of brothers that ran a bakery and a candy shop in Little Sicily, was particularly ambitious in growing the enterprise. Lombardo and Aiello operated a major wholesaling operation on Randolph Street near Aberdeen, of which Lombardo made Aiello president.

In 1926, the two, along with Ferraro, purchased land on Kinzie St., between Halsted and Green streets from an old steel yard, intending to open a fruit market. By that time, Lombardo was known as a major figure in the underground liquor trade, having been recently involved in a high-profile case involving abuse of licenses granted to synagogues for sacramental wine. The Tribune reporter included a wink and a nod in the story noting the real estate transfer:

A wholesale fruit market, with an accent on grapes (what does this mean, Watson?), is to be opened by Giuseppi Aiello, Antonio Lombardo and Joseph Ferrara, on an irregular shaped piece of property fronting seventy-six feet on Halsted street, 125 feet on Green street, 252 feet on Kinzie street and 252 feet on a paved court.

The three bought the property, which is now covered by the Kennedy Expressway, for $176,799, with a down payment of $45,000. It was shortly after this that Aiello and Lombardo fell out over Aiello's ambitions for greater control in the business (later, a lien would be placed on the property when Aiello failed to pay his share of the mortgage). Aiello also coveted the presidency of the Unione Siciliana, a position Lombardo held at that time.

(Pictured: Letterhead for Lombardo grocery concern on Randolph St., with Aiello listed as president)

The death of Unione president Mike Merlo in 1924 led to the assassination of Dion O’Banion, likely at the orders of Capone and Torrio, and in the subsequent bloodshed, the city’s bootlegging business was divied between rival gangs, with Capone and Torrio controlling the south side and Cicero, and O’Banion’s followers “Hymie” Weiss, George “Bugs” Moran, and Vincent “Schemer” Drucci taking hold of the north side. Lombardo and the Gennas worked with the Torrio-Capone syndicate, with Angelo Genna succeeding Merlo to the presidency of the Unione.

When Angelo Genna was killed in 1925, Sam “Samoots” Amatuna became president of the Unione, but only for a brief period before he, too, was assassinated. Then, it was Lombardo who became “Don” to the city’s Sicilian population. The presidency of the Unione Siciliana, which claimed 15,000 members, involved substantial political influence over an important voting bloc, and so it created the opportunity for the one who held that position to become a “fixer” with connections in city hall. Control of the Unione was thus highly important for the Capone bootlegging business, which relied not only on the network of Sicilian amateur distillers which pledged their loyalty to the Unione president, but also on Unione-connected politicians and police officers to look the other way, or even work proactively against competitors. The Unione presidency was also an position of great community esteem, prominent in resolving disputes and feuds among Sicilians, including “Black Hand” extortion plots, which were especially problematic at that time. Thus, Lombardo was a real-life Chicago version of Vito Corleone.

However, the connection between the Unione and organized crime had become fixed in the public’s mind, and Lombardo sought to change this impression by renaming the Chicago chapter as the "Italo-American National Union" and allowing non-Sicilian Italians to join. The name change angered some, including the president of the New York branch of the Unione, powerful mobster Frankie Uale.

The Italo-American National Union also contributed prominently to charities, including, for example, hurricane relief in Florida in 1926. It attempted to raise its profile as a leading civic organization by inviting important Italian politicians to Chicago. At the time, Benito Mussolini had recently consolidated control of that country, and so Lombardo brought Mussolini’s U.S. ambassador to Chicago for a prominent series of speeches promoting fascism:

God sent Benito Mussolini to an imperiled Italy and did, thereby, a service to all the world, Baron Giacomo de Martino, Il Duce's ambassador to this country, yesterday declared three times during the first day of his three day visit to Chicago. And three times yesterday groups of the ambassador's countrymen, once at the Italian Chamber of Commerce luncheon at the Drake, again at the Italo-American union massmeeting at the Coliseum, and last at the union's dinner at the Palmer house -- jumped to their feet and cheered mightily as they shot out their right arms in the Roman salute of Fascism.

After his falling out with Lombardo, Joseph Aiello allied himself with the Northsiders, Weiss, Moran, and Drucci. Aiello knew that, with control of the Unione, the North side gang could take control over the entire Chicago alcohol business, and reap hundreds of millions of dollars in profits. He also coveted the social standing that Lombardo held in the Sicilian community, and the jealousy made him murderous.

In one instance, Aiello allegedly offered $35,000 to a chef to poison Lombardo and Capone. In another case, he offered Torrio-Capone ally Ralph Sheldon $50,000 for each of the heads of Capone and Lombardo. Capone offered peace to the north side gang by offering to divide the city along Madison street, which led to a brief ceasefire, but before long, Aiello’s ambitions on the Unione presidency, and Lombardo’s ruthlessness in maintaining it, led to more bloodshed.

Early in 1927, police uncovered a stash of weapons and ammunition in a sniper nest across the street from Lombardo’s home on W. Washington St., near Cicero Ave., and a similar one at the Atlantic hotel, across from Alderman Michael “Hinky Dink” Kenna’s post-Volstead headquarters on Clark St., where Capone and Lombardo were frequent visitors. When Lombardo realized the extent of Aiello’s bloodlust, he moved his family out to a more easily guarded single-family home on S. Austin Blvd. in Cicero. But he knew that eventually either he or Aiello would meet an early grave.

After the discovery of Aiello’s weapons caches, the police arrested him on weapons charges and placed him in a cell at detective headquarters. In the adjoining cell they placed three Capone gunmen who had also been caught with illegal weapons while searching for Aiello, and a police officer who spoke Italian hid nearby, listening in on the conversation. The officer’s report refers to Capone’s frequent alias, Al Brown:

"Can't we settle this thing?" Aiello then pleaded with the trio. "Give me fifteen days, just fifteen days, and I will sell my stores and my house, and leave everything in your hands. Think of my wife and my baby, and let me go."

The Brown [Capone] gangsters gazed at their subdued foe scornfully and replied, according to the listening policeman:

"You dirty rat, you started this thing. We'll end it. You're as good as dead now."

Nevertheless, Aiello did manage to escape after the incident, and fled to New York, where he remained for a year, no doubt spending plenty of time commiserating with Frankie Uale about their shared dislike for Lombardo.

With Aiello out of town, Lombardo relaxed his guard, and even helped Capone go on the offensive. When, in November, 1927, the gang discovered north side gambling operations on Monroe St., two blocks south of the Madison Street border, bomb explosions there served as a "final warning." When questioned by a reporter about the bombings, Lombardo replied:

"Me, a bomber? Go to the people who know me best. Ask the Italians of Chicago if I am a bomber. Find one of them who will say I am a criminal. You can't do it."

It’s unclear whether this was supposed to be exculpatory, or simply a statement of Lombardo’s absolute power in the Sicilian community.

(Pictured: Antonio Lombardo)

By 1928, Joseph Aiello was back in Chicago, and again plotting a takeover of the Unione Siciliana. Lombardo still stood in his way, but not for long. On September 7, 1928, at 4:30 p.m., Lombardo, his long-time business partner Joseph Ferrara, and a bodyguard, Joseph Lolordo, stepped out of the offices of the Italo-American National Union in the Hartford Building at 8 S. Dearborn St. They walked north towards the corner of Madison St., where a large crowd had gathered. Across the street at the Boston dry goods store, an airplane was being dragged up the side of the building up to the 11th floor by ropes, and into a window, for a store promotion. Practically everyone on the scene was focused on the unusual sight -- everyone except two mysterious men from out of town, dressed in dark gray suits.

50 feet west of Dearborn, on the south side of Madison st., at the corner of the Hartford building, and just in front of a Greek restaurant, Tony Lombardo turned to his bodyguard.

“Look at the airplane,” he pointed across the street.

At that moment, the two men in gray appeared out of the doorway of the Greek restaurant, ran up behind Lombardo, and unloaded their revolvers into the Unione president’s head, also shooting Ferrara in the back, before dropping their guns at the scene and running east on Madison. Lombardo’s bodyguard, Joe Lolordo, took off running after them, while the panicked crowd of bystanders scattered.

Gunmen and policemen ran here and there with waving guns, men and women in the crowded street jumped first one way and then another, wondering from which direction the next bullet might come. People in stores ran out, then ran back in. Which way safety lay they could only guess.

A police officer tackled Lolordo, thinking he was one of the assassins, while the real assassins ducked into a nearby shoe store, exiting out the back and escaping the chase. Antonio Lombardo, president of the city’s largest Italian group and a major underworld figure, died on the street, shot to death in broad daylight in front of thousands of witnesses at one of the city’s busiest intersections. In the photo at the top of this post, the spot of the shooting is on the sidewalk, roughly at the right-hand end of the wooden scaffolding.

(Pictured: scene on the street at the site of Lombardo's shooting)

A week later, Ferrara also died of his wounds. Following underworld protocol, he refused to cooperate in the police investigation of the shooting before his decease, but based on identification by another eyewitness, Frank Marco, a New York hoodlum and a known acquaintance of Aiello’s, was charged with the crime. Marco wasn’t located, however, until his bullet-riddled body was found on E. 19th street in New York City in February, 1930. No one else was ever charged with the crime, but everyone assumed the hit must have been ordered by Aiello, possibly with the assistance of Frankie Uale’s gunmen from New York.

After Lombardo’s death, his bodyguard's brother, Pasqualino Lolordo, took over the presidency of the Unione, until Lolordo, too, was shot and killed at his home in January, 1929. According to most sources, Aiello finally did become president of the Unione Siciliana for about a year while Capone was in prison in Philadelphia on weapons charges. But when Capone returned to Chicago in 1930, Aiello made plans to flee the country; however, a sniper's bullet found him first.

The Hartford building, where Tony Lombardo’s Unione Siciliana headquarters were on the 11 floor, and in front of which he was killed, was built in 1893. Standing at 14 stories, it was one of the city’s tallest. It was destroyed, along with all other buildings on the same block, in 1965 to make way for the First National Bank Building, now called Chase Tower.

"Terrible Genna" Headquarters

The Genna brothers, Pete, Sam, Jim, Tony, Angelo, and Mike, organized the massive dispersed labor force that produced distilled spirits for the Torrio-Capone syndicate during Prohibition. Their warehouse and headquarters, disguised to almost no one as an olive oil and cheese import business, was located on this parking lot, at 1022 W. Taylor, in the heart of Chicago’s Little Italy. The Gennas were the most crucial element in the liquor supply chain, and control over their operations was largely the source of the bloody Chicago Beer Wars of the 1920s.

There were seven Genna Brothers born in Sicily, and six of these came to America in 1910, settling in Chicago. They represented the worst of the dark, superstitious, and vengeful stereotypes of that island, and most everyone – the police and even other violent gangsters included – was deeply afraid of them. They got their start as Black Hand extortionists and as enforcers for Italian politician Tony D’Andrea in his long-running and violent feud with rival 19th ward alderman Johnny Powers. After D’Andrea’s assassination in 1921, the Gennas took control of the old D’Andrea headquarters at 1022 W. Taylor, known as the Italian-American Educational Club, and began reorganizing D’Andrea’s constituents into a massive and dispersed distilling organization.

Jim Genna was the oldest and the leader of the clan. Pete started as a saloonkeeper on the Westside and was the master of operations in the business. Sam was the political connection, Angelo supplied the tough guy muscle, and Mike was the runt of the family, subordinate to the others. Tony was a self-styled aristocrat, working as an architect and living at the posh Congress Plaza Hotel on Michigan Avenue. He publicly disdained the criminal activities of his brothers, although when needed, he helped out in the family business as well, and in fact, he eventually gave his life for it.

The photo below shows the Genna family at the height of its power. From left to right, the men in the picture are Sam, Angelo, Pete, Tony, and Jim. Mike was likely the photographer.

The purpose of the Volstead Act, otherwise known as federal Prohibition, was to reduce alcohol consumption, which it did to a mild degree: a study of cirrhosis death rates indicates that alcohol consumption declined around 10-20% during the 1920s. At the same time, Volstead had a number of important unintended consequences, particularly for the way illegal alcohol was produced.

Since large distilleries would be difficult to keep hidden from law and revenue enforcement officials, and because a single raid on such an outfit could have a major impact on profits, the Gennas devised an ingenious method of dividing up their operations among thousands of small back-room stills. They offered $15 per day (a pittance of their profit, but roughly three times average unskilled labor earnings at the time) to each Sicilian family that would keep 50 gallons of corn sugar alcohol “cooking” in their home. Largely illiterate and impoverished, but accustomed to the home distilling process from life in the Old World, these families were more than willing to comply, and so all the streets of Little Italy reeked with the sweet smell of Genna mash. Through the inability to take advantage of the substantial economies of scale in distilling, Prohibition led to an enormous waste of societal resources, including the labor of thousands of immigrant Sicilians, drawn into the industry by the Gennas.

Prohibition also severely limited the ability of alcohol producers to brand and advertise their product and so build public reputations for quality. In doing so, it eliminated incentives for producers to engage in quality controls common in legal industries. Indeed, the Gennas’ product was disgusting and often deadly. Ordinarily, scotch and whisky achieve their amber hue and smooth flavor through a lengthy process of aging in wooden casks. Genna spirits, on the other hand, were no better than industrial quality, colored with food dye, and cut with glycerol in order to make it swallowable. Police raids in later years found dead rats and other impurities in the liquor barrels stored at the warehouse. These issues led to frequent alcohol poisonings, blindings, and deaths in Chicago that, in a legal market for booze, would have turned the Genna brand name to mud and scared customers away.

A third consequence of Prohibition was increased levels of violence as alcohol producers could no longer rely on the legal system to adjudicate disputes with employees, suppliers, and each other. The Gennas were among the most violent gangsters in Chicago history. In May, 1921, Angelo Genna was arrested for the murder of Paul Labriola, a supporter of Tony D’Andrea’s political rival. Twenty-five witnesses from the Club the Gennas later controlled as their headquarters testified that Angelo had been at the Club during the shooting. Moreover, on the last day of the trial, the state’s chief witness changed his story and claimed he had been paid to finger Angelo Genna as the killer. Genna went free.

Less than a year later, Angelo Genna was again arrested for murder, in this case of Paul Notte, in a long-running family feud. Notte named Angelo as his assassin with his dying words, but the testimony was thrown out of court when it was revealed that Notte was under the influence of medication at the time of his death. Again, Angelo went free.

He was not quite so lucky later in 1922, when he was arrested for threatening to kill Genevieve Court, a 15 year old girl who was prepared to testify in a Mann Act case against a Genna family associate, Henry Maltese, that Maltese had kidnapped her to Milwaukee and raped her before attempting to sell her into prostitution. Angelo Genna told Court that she and her family were marked for death if she testified. On the day of her testimony, Angelo sat in the gallery directly opposite the witness stand and gave her the famous Italian “Look,” reminding her of his threats. She recanted on the stand, but later admitted to police what Angelo had done. So fearsome was Angelo’s reputation that in this case, local officials refused to enter Little Italy to serve his arrest warrant. Federal marshals, however, did arrest Genna, and he was convicted and served one year at Leavenworth prison. Angelo Genna is pictured below:

Corruption of public officials was another inevitable consequence of Prohibition, and Genna headquarters was so frequently visited by police officers receiving bribes that it became jokingly known as “the police station.” The Gennas paid out over $8,000 per month in bribes to over 300 officers, mostly from the nearby Maxwell district stationhouse. After the Genna empire tumbled, police “raided” the headquarters and produced a few barrels of liquor for the press, but the true purpose of the raid was to destroy as much evidence of their graft as possible (and to steal and sell the rest of the booze in the warehouse).

By 1923, the Gennas' alky-cooking labor force had become the source for most of the distilled spirits sold by the Syndicate run by Johnny Torrio and Al Capone. Though neither Torrio nor Capone were Sicilians, they cultivated close ties with Mike Merlo, the president of the Unione Siciliana, a political and community organization widely trusted among Little Italy’s Sicilian populace.

One person upset by this partnership was Dion O’Banion, the leader of the Northside gang, which was nominally connected to – or at least at a truce with – Torrio and Capone. Like the Gennas, O’Banion’s gang specialized in spirits, and when the Gennas began selling on the Northside, the former alterboy-turned-singing waiter-turned-florist-turned-gangster O’Banion sought revenge.

“To Hell with the Sicilians,” he was heard to say, and he began hijacking trucks distributing Genna liquor. The Gennas probably would have killed O’Banion immediately, but Torrio and Merlo imposed peace for the sake of business interests and profit.

However, after O’Banion framed Johnny Torrio during the May, 1924 raid on Seiben Brewery, and after Mike Merlo died from natural causes on November 8, 1924, no one was left to shield the Northside Irishman from Sicilian vengeance. Two days after Merlo's death, on November 10, 1924, Mike Genna and two feared Sicilian hitmen, John Scalisi and Alberto Anselmi, killed Dion O’Banion in his flower shop on State St., starting a feud between the Northsiders and the Torrio-Capone Outfit that would last the rest of the decade, culminating in the St. Valentine’s Day Massacre.

The end of the Genna empire came quickly and spectacularly. In May, 1925, Angelo Genna was shot while driving his car, sending him careening into a lamppost on Ogden Ave. One month later, in June, Mike Genna (pictured below) was in a car with Scalisi and Anselmi that ended up in a wild high-speed chase with police through the streets of the Southside. After the car carrying Genna crashed, a shootout took place which ended the lives of two police officers and Mike Genna. The next month, July, saw Tony Genna, the aristocratic architect, murdered on a Westside street corner. With their ranks thinned by 50%, the three remaining brothers quit the Chicago rackets and fled back to Italy.

The murders of Tony and Angelo, and the rationale for the battle that killed Mike, were never known with certainty. The most likely theory involves revenge attacks by O’Banion’s followers, who blamed the Gennas for their leader’s death. At trial, Scalisi and Anselmi, who survived the gunplay that killed Mike Genna, claimed they had been involved in a shootout with Northside gangsters “Schemer” Drucci and “Bugs” Moran earlier in the day; thus, they mistakenly believed the police cruiser tailing them was Drucci and Moran pursuing a continuation of the battle, and the shooting of the two police officers was thus self-defense (they also conveniently claimed the shooter was the dead man, Mike Genna).

An alternative theory is that the Gennas had become powerful and rich enough to do without Capone, and were planning a takeover of the Big Fellow’s operations. In this theory, Capone became aware of the plot and hired Scalisi and Anselmi to kill Angelo and Tony, and to take Mike Genna “for a ride,” which they were doing when they were surprised by the police, starting the shootout.

In any case, the “Terrible Genna” reign of terror in Chicago was over by the fall of 1925, although there were other gangsters only too happy to pick up where they had left off. Jim Genna (pictured below) continued his criminal behavior in Italy, serving two years in prison there for jewel theft. Later, he entered into respectable business, operating a vacuum repair shop in Rome. Pete and Sam lived the rest of their lives in anonymity.

Public outrage over the Gennas’ crimes, and the Sicilian community’s complicity, reinforced political attempts to limit Southern European immigration. Even the Tribune cited the example of the Gennas in a 1926 editorial, published during Scalisi and Anselmi’s trial, using rhetoric that just as easily could have come from commentators in some quarters today:

As long as this country permits the importation of murderers, so long will it make little progress in suppressing murder. The city and state officials are not chiefly to blame; the responsibility falls directly upon the federal government. The immigration laws are not enforced. The examination of prospective immigrants is not sufficiently rigid. The sifting process is bungled. The meshes are too large and the work is too hasty. Men whose criminal records might easily have been learned are permitted through carelessness or indifference to enter the country. If by chance a criminal is excluded at Ellis Island he is able without much difficulty to cross the border at another point. There are countrymen of his within the gates to give him a helping hand.

After Prohibition, the Genna headquarters building was converted into a hardware store owned by the Chiarugi family, which remained until the mid-1960s, when it was demolished in urban renewal efforts (the Chiarugis moved their shop a few blocks west, where it exists today). The spot holds a parking lot today. The Little Italy neighborhood, far from the impoverished slum it was only a few decades ago, is a desirable and gentrified town-and-gown neighborhood, home to many students and faculty from nearby University of Illinois at Chicago.

"Schemer" Drucci Killed by Police Officer Healy

Vincent Drucci was a teenage pickpocket and thief when he became close with the Northside gang, run by Dion O'Banion. Eventually, he became their leader.

Besides being a racketeer and notorious criminal, Drucci was a first-class goofball. He earned his nickname, "Schemer", for the wild, harebrained ideas he was constantly dreaming up for stealing the crown jewels, bringing down the U.S. government, running for Mayor, or some other equally ridiculous plan. As a practical joker, he was unparalleled among gangsters, and was famous for walking around dressed as a priest, while making mischief among those he happened to come across.

He rose through the O'Banion organization, becoming second in command under "Hymie" Weiss after O'Banion's death, and taking over the leadership when Weiss was assassinated. A ruthless killer, he held the distinction of murdering two consecutive presidents of the Unione Siciliana, Angelo Genna and Sam Smoots Amatuna.

He made countless attacks on the lives of Al Capone and other members of the Torrio-Capone syndicate. During 1926, while Capone was sequestered away from Chicago in Lansing, Michigan, waiting for the heat from the Bill McSwiggin murder to pass off. The Northsiders took this opportunity to expand the reach of their gang. When Capone returned to the city, he decided to send a message to Drucci and company. One of Capone's loyal deputies, Louis Barko, engaged Hymie Weiss and Drucci in a firefight through the streets of the Loop, leading to Drucci's arrest. It was this event that triggered the Northsiders' revenge attack upon Capone's Cicero headquarters, the Hawthorne Inn.

Schemer Drucci's run of luck ended in a rather inglorious way. April 4, 1927 was mayoral election day in Chicago. "Big" Bill Thompson, the Republican candidate who had previously served as second ward alderman and whose career was guided and mentored by the corrupt vice king-aldermen of the first ward, Hinky Dink Mike Kenna and Bathouse John Coughlin, was running on a "wet" platform against "Decent" William Dever. For his anti-prohibition stance and general amenity to corruption, Thompson was gangland's choice, and Drucci decided to help his man in the best way he knew -- by kidnapping Dever's supporters. After breaking into the office of Dever's biggest supporter on the City Council, Lincoln Park Alderman Dorsey Crowe, Drucci managed to get arrested and, after some legal wrangling, ended up in a police car headed for the Criminal Courts building downtown.

His police escort included one of Chicago's toughest cops, Dan Healy. Healy's description of what took place during that car ride follows:

Drucci said, "You -- I'll get you. I'll wait on your doorstep for you." I told him to shut his mouth. Drucci said, "You take your gun off me or I'll kick hell out of you." He got up on one leg and struck me on the right side of the head with his left hand, saying "I'll take you and your tool. I'll fix you," grabbing hold of me by the right hand. I grabbed my gun with my left hand and fired four shots at him."

Drucci was shot in the back of the police cruiser while stopped for traffic on the Clark Street bridge over the Chicago River, pictured above. Despite pleas from his attorney, Healy was never seriously investigated for the killing, since the police were more than happy to see Drucci gone. Even Drucci's widow found her self less than distraught over the decease of the gangland leader. Inheriting his half-million dollar estate, she is reported to have said at his funeral (organized by John Sbarbaro, of course), "We sure gave him a great send off."