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.