The Roaring Twenties were a time period filled with tales of adventure and glamour. Prohibition fueled a party lifestyle - and made available a dangerous but adrenaline fueled life to some of the more enterprising members of the underworld. In Chicago, Illinois, the Twenties have become a time of legend and usually call to mind one man, Al Capone. But Capone, for all intents and purposes, was only a figure head during the Beer Wars. He ran his gang and racket, but he delegated the dirty work.
To the north of him was a group that was, as one newspaper of the time called them, Modern Day Pirates, The North Side Gang. Consider Capone the Prince John to their Robin Hood and his Merry-men, an analogy that Rose Keefe introduced in her book, Guns and Roses: The Untold Story of Dean O’Banion. Robin Hood isn’t quite as steal from the rich to give to the poor and you’ll need to give Little John a temper and thirst for vengeance that was unrivaled. Also, make the merry-men a little crazier and a lot more deadly. You get the picture.
If you asked Vincent Drucci what his biggest fear was, it might have taken him awhile to answer. He was reckless and seemingly fearless with a massive disregard for anyone’s personal safety but especially his own. His past times included jumping bridges, riding on the sides of speeding cars, dressing as a priest and stealing his friends’ shoes. And though he wouldn’t admit it to you, it is possible his biggest fear was losing everyone he loved. And by the winter of 1926, that was beginning to seem like a likely reality for him. So, when he took over from Hymie Weiss, he made a decision that was probably not well liked but that he desperately needed.
Erin Finlen continues her series.
The mausoleum of Vincent Drucci at Mount Carmel Cemetery, Hillside, Illinois. Source: Nick Number, available here.
Early Life and Meeting His Crime Family
Sicilian gangsters of Chicago are most often associated with Cicero and the South Side, but there was also a small community on the north side of the city and that was where John and Rosa D’Ambrosio settled with their family. On April 27, 1899, they welcomed their sixth child of what would eventually be ten children, Ludovico D’Ambrosio, the Latin spelling of Victor. Not much is known about Victor D’Ambrosio as a child. Census records indicate that he went to school and that he learned to read and write. It is most likely that he was supposed to enter the family construction business at some point. However, his temper and need to continuously be moving, paired with a tendency towards dreaminess made him a poor fit.
He joined the Marines when the United States became involved in World War I and ended up shell shocked and with little disregard for life when he came home. None of this served to make him a better employee for the construction business, either the work itself or the customer service part of it and, since his father had passed away in 1916, there was no pressure to stay on in the job he hated and for which he wasn’t well suited. Crime seemed a much better career path for him.
While he started robbing phone boxes he eventually met Dean O’Banion and Hymie Weiss, as well as George Moran. Dean, despite his rumored hatred of Sicilians could speak a little of the language and found in Victor, now calling himself Vincent Drucci, a kindred spirit. Both men were charming, fun loving with violent tempers. Where O’Banion was quick to settle his problems with a gun, Drucci was more likely to create a scenario that was so outlandish and crazy that at times you had to let him do it, if only to see if it would work.
This wild imagination earned him the nickname ‘Schemer.’ His plans did not just revolve around his current life of crime though. At one point he is rumored to have come up with a plan to get himself to the US presidency. It was all illegal, of course, but no one could ever accuse Vincent Drucci of thinking small.
Cinema Style Gangster
When he joined with O’Banion, Weiss, and Moran, it was like he had found four extra brothers. Weiss was his older brother that he could needle and poke but who would always still adore him. O’Banion was the older brother who taught him how to poke Weiss and encouraged him in his mischief making and prank pulling.
His best known prank took place on the busy State Street. Somehow, Drucci came into procession of a priest’s collar and robes. He would regularly stand outside Schofield’s (yes, directly across from a Catholic Church) and yell obscenities at passersby. Once, O’Banion came out to join, pretending to be offended and beating him up.
A driver for the North Side Gang remembers Drucci coming to ask for his keys so he could move his car, without a second thought he handed over the keys. When Drucci returned he simply handed the keys back without a word and walked away. It wasn’t until the man went to his car that he found out why he had been so tightlipped. Drucci had filled the man’s car with freshly shoveled snow from the sidewalk. Dean, while he paid to get it cleaned, couldn’t help finding it to be hilarious. And then, there was the “Shoe” game, which more than likely got Drucci in fights often enough, but the only example we have is from when he pulled it on the serious and temperamental, Weiss.
The Shoe Game involved someone wearing a new pair of shoes. When he spotted the shoes, Drucci yelled the word “shoes,” and tackled the person, stealing them off their feet. Weiss was his victim one day and somehow not only did Drucci get the shoes off but managed to chuck them out the second story window of Schofield’s. Weiss’s head appeared to the pedestrians below, politely asking them to bring up his shoes. The person who brought them up remembered Vincent howling with laughter while Weiss cursed loudly. For a man with a temper that got his brother shot, Weiss was clearly not angry enough with Drucci to really lose his cool and loved him dearly. Not to mention, it was an example of the fearless of Vincent Drucci. But no one doubted that. Not after the bridge jump, something straight out of a movie.
At the end of August in 1922, Drucci was involved in a chase with police, wanted for forfeiting his bond from a safe cracking arrest, when he came to the DuSable bridge on Michigan Avenue and the gates just coming down for the bridge to rise, letting a barge through. A common occurrence in Chicago and one that should have been the end of the chase. Not one to be thwarted by something as trivial as a gap in a bridge, Drucci, put the car in gear, pressed the gas, broke through the barrier and successfully jumped the bridge. Unfortunately, the two police officers did the same and Drucci encountered a traffic jam. It made headlines and has become a legend in the Chicago history.
Violent Temper, Broken Heart
None of this is to say that Vincent Drucci was simply a fun loving guy on the wrong side of the law. He was a violent, dangerous man when crossed or on a bad day. There was a new gun law in Chicago in 1925 staying that it was illegal to carry a concealed weapon. Drucci was arrested but then walked free, fined $300 by a judge. According to most people who were there, Rose Keefe says in “The Man Who Got Away,” Drucci “seemed amused by the whole thing.” And then a detective chose to make an example of him on the steps of the courthouse, saying he would frisk him every time he saw him.
Drucci did try to avoid carrying a weapon after that but between the feeling of paranoia and gang war he was involved in, he didn’t have much patience left to be tested. When he was denied use of a telephone at a local business, he turned on his heel and went back out to his bodyguard, asking to borrow his gun. He didn’t shoot the man, instead he beat him over the head with gun. The man had to be treated for scalp wounds at a nearby hospital.
The attempt on his life and that of Hymie Weiss outside of the Standard Oil building in August of 1926 was really just par for the course for Drucci by that point. As was attempting to escape on the running boards of another car. And the hit on Capone at the Hawthorne Hotel, despite Weiss being credited as the mastermind behind it, seems to have all the signature pieces of a Vincent Drucci plan. There was nothing subtle or sophisticated, except maybe the firing of blanks. And it wasn’t effective in the way they had hoped for. Since the three men—Weiss, Drucci, and Moran—never declared a true leader, they all had a say in it, but it feels like a Vincent Drucci scheme more than a Hymie Weiss plan. And it’s too thought out to be a George Moran plan.
On October 11, 1926 when he heard of the shooting of his best friend, Hymie Weiss, between Schofield’s and Holy Name Cathedral, he jumped in his car and headed for the scene. Thankfully, someone stopped and gave him the update, Weiss was dead. Drucci turned the car around and going back to his hotel, emptied it of his necessities and went into hiding. He appeared at the funeral but the police avoided him, rightly thinking he would blow his lid if they questioned him there. On October 17th, the police did take him in for questioning while he was sitting at a Cubs game. He refused to say anything, telling the police he had been in New York. An obvious lie, but the police had been through this enough by now and chose not to press it. If a gangster wasn’t going to tell you, he wasn’t going to tell you and nothing would make him.
The loss of Weiss put Drucci in charge, more or less, of the North Side Gang and he agreed to peace terms with Capone. It was the agreement of a man who had lost too many friends already, not to mention his dad and then in 1924, a much younger brother had passed as well. In his family life and criminal life, Drucci had had enough.
A Short Reign
Drucci wasn’t completely done with his prankster ways though and shortly after taking over, he and Moran managed to impersonate police officers and pretend to raid some alcohol…from the police. How he did this is unclear but the police force was very unhappy and embarrassed.
In the biography of Joe Lewis, a comedian of the twenties, called “The Joker is Wild,” Lewis gave insight into how Vincent Drucci had calmed a little after the deaths of his two best friends. He closed a speakeasy called “The Green Mill,” almost every night and would walk back to the hotel that both he and the comedian had rooms in, with Lewis. He was considered a calm and polite and a genuinely friendly guy. At some point over the years, he had gotten married, but far from being a calming influence on him, his wife Cecilia was just as feisty and tough as her husband.
Things all seemed to be going well, until election day, April 4, 1927. The North Siders and the South Siders were working together to get Big Bill Thompson elected as mayor of Chicago again. Drucci was apprehended by police officers for threatening people voting against Thompson. One of the policeman was Detective Dan Healy, a straight cop with a short fuse who never took bribes and loathed gangsters like Drucci. He had already shot one thief the previous year and almost a second in November. Drucci and Healy were already on unfriendly terms and it seems Drucci was in a bad mood. Even before they had made it to the car the two were arguing as Drucci had called Healy a name for holding him too tight and Healy had pulled his gun and threatened to shoot him. Inside the car it didn’t improve, Drucci and two of his associates sat in the backseat with Healy and another officer, and two more officers were up in the front seat. As the drive continued Healy and Drucci’s argument grew more intense until Healy shot him three times.
Depending on who you asked the story was a little different. The police officers, Healy, Sergeant Daniel Keough, Sergeant Matthew Cunningham and Lieutenant Liebeck, said that Drucci began by punching wildly at the car’s curtains. After that he jumped at Healy, threatening him and Healy shot him.
The two men who had been arrested with Drucci, Henry Finkelstein and Albert Singel, said that Drucci had been sitting with his hands in his lap when he was shot three times, in the leg, the stomach and the arm. He was taken to a local hospital which said he needed more assistance than they could give him and put him in an ambulance to the county hospital. He didn’t live long enough to make it.
Buried with military honors, Vincent Drucci was laid to rest in the family vault at Mount Caramel Cemetery, near where Hymie Weiss and Dean O’Banion were interred. In an outlandish display of flowers that the man himself surely would have appreciated, one funeral picture shows the letters, “VD” made out of flowers.
George Moran was taking over a gang that had lost two leaders in less than six months. He had his work cut out for him and he still harbored a hatred of Capone that no amount of “peace talks” would quench. Moran’s top men, the Gusenbergs, who had been around since the O’Banion days, became good friends with him. They had often been mistaken for each other, except in the near future, it would be their similar builds and looks that would save Moran’s life.
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Sources
Binder, J. J. (2017). Al Capone’s Beer wars: A Complete History of Organized Crime in Chicago during Prohibition. Prometheus Books.
Burns, W. N. (1931). The one-way ride: The Red Trail of Chicago Gangland from Prohibition to Jake Lingle.
Keefe, R. (2003). Guns and roses: The Untold Story of Dean O’Banion, Chicago’s Big Shot Before Al Capone. Turner Publishing Company.
Keefe, R. (2005). The Man who Got Away: The Bugs Moran Story : a Biography. Cumberland House Publishing.
Kobler, J. (2003). Capone: The Life and World of Al Capone. Da Capo Press.
Sullivan, E. D. (1929). Rattling the cup on Chicago crime.
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