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.

Part one is here, and part two is here.

*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.

PostedFebruary 22, 2025

AuthorGeorge Levrier-Jones

Categories20th century, Blog Post

TagsVincent Drucci, Ludovico D’Ambrosio, The North Siders, 1920s Chicago, Prohibition

CommentPost a comment

Hymie Weiss more than likely would look back at 1924 as one of those years where everything and anything just seemed to have gone wrong for him. It had all calumniated in the death of his best friend and mentor in November. When Dean O’Banion died, Hymie said everything he had in the world was gone. But that didn’t mean that he was going to stand by and let it stay that way. He mourned his friend, buried him and then began a campaign of vengeance.

Erin Finlen continues her series.

Part one is here.

Grave of Hymie Weiss at Mount Carmel Cemetery in Hillside, Illinois. Source: Nick Number, available here.

Childhood

West Division Street ran through the middle of the Polish neighborhood of Bucktown on the West Side of Chicago and at 2021 W. Division Street was a saloon that was run by William Wojciechowski and his wife Mary. The pair had moved from New York with their children, Joseph, Bernard, and Frederick. In Chicago, they welcomed another daughter named Violet. Then, on January 25, 1898, the youngest of their children, Henryk Josef Wojciechowski, was born, although he would later change his name to Earl, saying it sounded like royalty. His mother would eventually decide to Americanize their last name to Weiss, although not legally.

He was enrolled at a school, St. Malachy’s on Washington, where he, from all accounts was a smart child with lots of friends, adored by his teachers. One even gave him a pocket bible which he would carry in his pocket for the rest of his life. The influences of the saloon life ran deep, and in 1913 his oldest brother, Joseph, was arrested and charged in the murder of three men. According to Joseph and his father a fight had broken out and Joseph was acting in self-defense. He was acquitted. However, rumors soon started circulating in the newspapers that the trial had been fixed and Joseph moved to New Mexico, where he died from Tuberculosis. Whatever the effect this had on Jospeh’s younger siblings is hard to say, as at this time Henryk would have been sixteen and already involved in crime on his own. He had also taken the name Earl.

Hotheadedness and violence seemed to run in the family though, as William, his father was arrested and injured in a labor dispute in Buffalo, New York in 1894 and Fred, Earl’s brother, was also considered to have had a formidable temper as well.

For the most part though, young Earl was no different than most other boys his age, involved in street gang wars from the time he was ten. He wasn’t the healthiest and had suffered from headaches for a long time. In 1918, he tried to join the army but was denied, as his draft card says, for a “double rupture” in his heart. At the time, Weiss was angry, annoyed that he couldn’t serve his country with the skills he had earned on the street. History, though, had different plans for Earl Weiss.

The Making of an Outlaw

Weiss was not an outwardly friendly individual and he was even less adept at making friends with newspapermen, telling them, “If you take my picture, I swear I’ll kill you.” Making an enemy of the press had earned him a much hated nickname, “The Perfume Burglar,” after he tried to rob a store, knocked over the perfume counter and was arrested smelling strongly of multiple scents. Eventually, the press and the underworld gave him a new nickname, “Hymie,” because of his outwardly Jewish appearance, even though he was catholic. He didn’t mind the nickname and seems to have let it stick.

After being turned away from military service he turned his criminal pursuits to safe cracking with Charles Reiser, where he met his mentor and best friend, Dean O’Banion. As discussed in Dean’s article the pair were a study in opposites and while Weiss is often branded the temperamental one it was he that was better at thinking through his actions and planning ahead. Unless provoked, of course.

In June of 1920 he shot his brother, Fred, in their shared apartment for a joke his brother made about Hymie not serving in the military (while newspaper articles at the time say that Fred served in the army, I have yet to find anything besides his draft card and his headstone does not bare the veteran symbol). In a fit of anger he shot Fred square in the chest and then, took him to a nearby hospital before running away. Fred survived and begged the doctors to not look into, although they reported it to the police anyway. The police arrested Weiss, but were not able to find any evidence to convict him.

In the meantime, he was busy helping Dean build their bootlegging empire with their friends Vincent Drucci and George Moran. They were making enough money now to be able to bribe most cops and judges. While they were bootlegging, they continued to pursue other criminal activities. In 1922, Weiss and Moran, under his alias of George Nolan were arrested after a police chase for stealing jewels. No charges were ever pressed all the police did have to fire shots to get the pair to pull over.

Illness and Mourning

At the same time, Weiss was making regular use of the couch that Dean had placed in his office for him. The regular headaches that had plagued him all his life were growing more frequent and the pain getting so unbearable he once had a fit on the floor of the North Siders garage. In early 1924, he left Chicago for Hot Springs, Arkansas in hopes of improving his health. While away, his brother in law and Dean were placed under suspicion for the murder of John Duffy and his name was brought into the equation due to the car being in his name. There probably wasn’t much of the hoped for relaxing on the trip.

When he returned he received a devastating diagnosis, he had terminal arterial cancer. This had been causing the headaches and fainting for so long. It was also the cause of that double rupture that had kept him out of World War I. He was given around two years to live and he intended to make the most of them. He is quoted as saying, “I’m not going to live long, but I will live long enough.” He just had to deal with fallout from Sieben Brewery raid.

It is suspected that he was the real mastermind behind ending the Torrio treaty. He was the thinker of the group but whether he didn’t consider the consequences or simply didn’t think they would be so severe, he still found himself mourning the loss of his best friend in November of that year.

A lifetime of an impulsive temper and hard knocks had taught Weiss a thing or two about revenge and as he drove out of Dean O’Banion’s funeral he was determined to make the people who took him from him pay.

Love and War

Weiss waited and he planned. From November until January he gathered information and observed. Then on January 24, 1925, when Johnny Torrio and his wife pulled up outside their home after a shopping trip Weiss and Moran with Drucci driving the car pulled up next behind them. After waiting for Anna Torrio and the dog to be clear of the car they fired on Johnny Torrio, hitting him multiple times. When he fell to the ground, George Moran ran up to shoot the fatal shot when a laundry truck came around the corner and Drucci blew the horn: it was time to go. Thinking they had done enough damage the North Siders fled the scene. Anna Torrio, a nurse ran to her husband’s side and slowed the bleeding until ambulances arrived.

When word reached Hymie Weiss that he had not succeeded in eliminating Torrio, who was now in critical condition but very much alive in a hospital he was furious. One nurses account gives us an idea of how he reacted when the planning and intelligent part of his brain gave way to the impulsive and angry emotions. She told authorities that a man had run up to the desk demanding to know where Torrio was. She refused, saying no one was allowed to see him, Torrio’s wife had insisted on no one but family and an approved few friends. The man insisted and the nurse, thinking quickly, informed him that there was an increased police presence at the hospital. The man left in hurry after that. The nurse later identified the man as Earl “Hymie” Weiss from his mugshot.

1925 was not off to an auspicious start in anyway and in April, Weiss appeared in court for charges from a bootlegging arrest the previous year. Having originally made a plea of not guilty, he changed it to guilty and in May would serve six months at McHenry County Jail. He was still able to keep in touch and visit with the other members of the North Side Gang and by this time it had become clear that he was the new boss, through his intelligence and the charm that he did have but regularly chose not to use.

When he got out in the fall of 1925, the Genna Gang was no longer an issue, being eliminated through the police, Capone, and Drucci and Moran. He seemed to have relaxed a little and that could be because fell in love shortly after his release.

He met a Follies’ Girl by the name of Josephine Simard in the lobby of the Congress and the two immediately hit it off. He even followed her to New York when she left and returned with her now as husband and wife.

She was what Dean had been for him, a ray of sunshine to his dark moods and while they did fight often—the famous scene in “The Public Enemy” (1931) where James Cagney shoves a melon into Mae Wests face is supposedly based off of Hymie Weiss shoving an omelet in Josephine’s face when she wouldn’t stop talking one morning— they were a well matched pair and seemed very happy together.

He might have cooled in his quest for revenge but his temper certainly had not. In June of 1926, when he was at a party raided by police, he forced the policeman to leave at gun point. The police obviously came back with help and Weiss and a friend were arrested. Weiss wasn’t done yet and filed a petition to be reimbursed for items he believed were stolen during the raid. The petition was quickly denied, but it seems that it might have stirred something of the old Weiss in him.

The Battle Resumes

In August of 1925, Weiss and Drucci, who had been a massive thorn in the side for Al Capone for a while were attacked by rival gangsters and involved in a shoot-out in front of the Standard Oil Building. Well, Drucci was. Weiss ran for cover and Drucci hopped on the running boards of a passing car, telling the driver to follow the assailants, before he was nabbed by the cops. Weiss telephoned his mother, Mary Weiss, who showed up at the police station to pay Drucci’s bail. Drucci’s explanation to police for the event was the gangsters were trying to rob him.

Police and the North Siders weren’t fooled. It was the Capone gangsters as retribution for the killing of Al Capone’s chauffeur, who it was believed was kidnapped and tortured for information about Capone’s routine by the North Side Gang (Note: John Binder, in his book “Al Capone’s Beer Wars” posits that this was probably not the North Side Gang and I am inclined to agree: it did not fit with any of the other crimes committed by the gang under Weiss. Torture of those not directly involved with a life of crime was not their style. It was more likely the Saltis gang behind the chauffeur’s death).

For a month, Hymie Weiss, Vincent Drucci, and George Moran waited before their next attack. The audacity and publicity of the attack has gone down in history as one of the more dramatic gangland attacks of all time. On September 20, 1926 a parade of cars pulled up in front of the Hawthorne Hotel where Capone was having lunch. They fired a first volley of blank ammunition to draw Capone outside and then the real firing began. The mess of shooting used somewhere around two hundred bullets and witnesses agreed they saw Hymie Weiss and Moran or one of the Gusenberg Brothers get out and fire Tommy Guns into the restaurant. One of the Capone gunmen from the Standard Oil Shootout was injured and so was a woman eating in the restaurant. Capone paid for her hospital bills.

Capone decided to give peace talks one more try but not in person, he sent a liaison. Capone was famously scared of Weiss and it’s easy to see why. Capone was a man with a lot to lose and Weiss, as he saw it, had nothing. Weiss told the liaison that he would agree to peace if Capone surrendered John Scalise and Albert Anselmi, who he knew were involved in the murder of Dean O’Banion, to the North Siders. Capone refused and Weiss left the meeting angry.

October 11, 1926, Hymie Weiss’s car pulled up outside Holy Name Cathedral, with four of his men. As he was crossing the street bullets from Thompson SubMachine Gun burst from the window of a nearby apartment. Weiss fell to the ground unconscious and died on the way to the hospital. Paddy Murray, a fellow gangster was also killed and the other three men were critically injured. The side of the church was broken with machine gun bullets and streets away, when Vincent Drucci heard the news he was distraught and newspapers reported that he was being held back from attacking the perpetrators.

Saying Goodbye

Weiss’s funeral wasn’t quite as big as O’Banion’s, a fact that irritated Josephine Simard, but Moran tried to gently explain that they had lost several friends to violence over the last two years. Mary Weiss was accompanied by her two sons and sobbed next to the coffin.

In the fall of 1927, the will of Earl J. Weiss was called into question and while Josephine tried to stand her ground she was no match for the formidable Mary Weiss, who refused to relinquish anything except the car that had been gifted to her (and even that was on court orders) without a marriage certificate, which Josephine could not produce.

Left with two bosses to choose from, there was really only one person to step in after Hymie Weiss died, the man who had loved him as a brother and the one who was nicknamed Schemer for his crazy plans, Vincent Drucci.