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.
Who was responsible for running this group of gangsters that, while small, caused a lot of trouble for the biggest figure of Chicago’s Underworld? That was none other than Dean O’Banion. Our figurative Robin Hood.
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Dean O’Banion.
Dean O’Banion
Dean O’Banion, or Dion as he is often misnamed in history, is considered the archetype of Irish Chicago Gangsters. An impulsive, faintly religious, prankster who was oddly chivalrous and loyal to a fault was the original boss of the North Side Gang during Prohibition and his death became the catalyst for what are known as The Beer Wars.
The Death of a Mother
Born in Maroa, Illinois on July 8, 1892, to Charles and Emma O’Banion, Dean was a middle child of three, with a big brother named Floyd and a little sister named Ruth. He was a good student and in one of the only surviving childhood pictures of him, taken at his school in Maroa, it is easy to see a precocious but loving child staring back. Maroa is a small town a few hours’ drive south of Chicago and away from the influences of the big city it is possible that O’Banion would have taken a very different path is things had stayed the same with his happy family to guide him.
Except, Dean was struck by a tragedy that no child is equipped to endure and certainly not back them when there was no therapy or mental health knowledge, not in the way we have now. When he was six years old, O’Banion’s mother passed away from tuberculosis and his world was shattered. He had loved his mother dearly and after her death not only did he lose her, but his father moved him and his older brother to Chicago in an effort to be closer to his own family and for better employment opportunities. His sister Ruth stayed behind in Maroa and ended up living in Kansas and having a family of her own when she was older.
Chicago, it’s His Hometown
The shock of not only losing him mother but then being uprooted from his childhood home and leaving behind his sister was probably traumatic and confusing. It would have given a much less optimistic child a pessimistic and depressed disposition. Dean, however, found that he enjoyed the adventure that was waiting for him.
In Chicago, he was enrolled at Holy Name School on State Street, but school only did so much to curb his impulsiveness and there was no stopping the influences of the neighborhood they lived in an area that was called “Little Hell,” and that lived up to its name with child gangs running the streets.
Then when he was sixteen, he went to hop on the back of a trolley car, slipping when he grabbed the handle, he fell and was hit by the wheels of the trolley. It broke his leg and he walked with a limp for the rest of his life. Given the state of medicine in the early 1900s, he seems to have had some of the luck of the Irish to have not had a worse outcome.
He eventually left school and started working, first as a singing waiter in a saloon, where he met the acquaintance of a criminal named Charles Reiser. Reiser would introduce him to safecracking, although, Dean, always a little trigger happy and impulsive, wasn’t the best at deciding how much nitroglycerin to use. His frame of mind was always ‘more is better’ and he had a tendency to ruin the contents of the safe when he blew it open, once blowing a hole in the wall of the building but leaving the safe unharmed.
Through Reiser and safe cracking he met the man who would become his best friend and right hand man, Earl “Hymie” Weiss.
Robin Hood and Little John
Weiss and O’Banion were friends from the start, a study in opposites. O’Banion was impulsive with a temper that was easily triggered but just as easily satisfied. He was jovial and people were drawn to him, wanting to be his friend. Weiss was serious, with a temper that was terrifying when he was set off and not nearly as easily calmed. Smart and forward thinking he was O’Banion’s perfect foil and the two almost seem to be made to rule the Prohibition scene. Which they began almost as soon as it started, with O’Banion hijacking the first truck and immediately starting his booze running racket. They were very successful and it showed.
They were also regularly in trouble together, but by that point they were able to pay off most juries and judges. When asked why they were robbing a telegraph office O’Banion said he was there to apply for a job. Similarly, when asked why his finger prints were at the scene of the crime, he replied with “That was an oversight. Hymie forgot to wipe them off.”
O’Banion’s biggest passion was the flower shop, Schofield’s, that he had bought stock in with his friend Sam ‘Nails’ Morton. Where Morton was content to be a silent partner, though, O’Banion preferred to work there, getting his hands dirty. One of the most notorious gangsters of his day was unrecognizable humming and arranging bouquets, while helping customers when they came into the shop. The store also his office. On its second floor he ran the North Side Gang, taking calls and meetings, he even installed a couch for Weiss, who was frequently laid low with migraines.
O’Banion loved to dress nicely and dine well. What he didn’t put up with was…well, it was a lot. Once in a restaurant he heard a man yelling at his wife. O’Banion intervened and wrestled the man to the floor. When someone made a barbed remark about them he shot them in a crowded theater. Afterwards, he realized what he had done and apologized, according to a newspaper man at the time, asking him what brand of cigars he should send him. When some of his drivers complained that one of the other men who worked in the garage was gay, he told them to deal with it or leave, that that was just the way the man was and he wasn’t hurting anything.
O’Banion, as evidenced by the man in the restaurant berating his wife, was not one to take a marriage commitment lightly and when he met Viola, who would become his bride. He was immediately smitten. The pair were deeply in love and when he died, she told reporters that the man she knew wouldn’t have hurt a fly. That he only carried a gun because of the danger in the city. Naive? Yes. Lying? Possibly. But it is very likely that the version of him that she knew was not the man who shot people in theaters or took men on one way rides, a term, by the way, that is credited to his best friend, Hymie Weiss.
Two of his other best friends and his other underbosses in the North Side were Vincent Drucci and George Moran. Moran and O’Banion were good friends, but the important one to look at here, is Vincent Drucci. Drucci was a Sicilian who had grown up on the north side of Chicago. When he came home from World War I, he fell in with O’Banion and his friends. Drucci offsets any rumors that O’Banion hated Sicilians, as the two played pranks together and would go to speakeasies, laughing and having a good time. It wasn’t Sicilians that O’Banion hated, it was just one family of them: The Gennas. They are the ones caused the most trouble and who would eventually lead to his death.
The Murder of John Duffy
At the start of 1924, Dean O’Banion was already in a bit of trouble, although no one could really pin the blame on him. A man named John Duffy had been found murdered in a ditch north of the city. His body was found with three bullet holes in it and when police went to his house they found the body of his girlfriend who had been shot dead by Duffy. No one questioned with the regards to the couple seemed at all surprised that Duffy would have murdered her and expressed concern for her. Duffy was not a well-liked man.
It was suspected that Dean O’Banion killed him, as Duffy was last seen getting into a car with O’Banion and one man who authorities later decided was James Monahan, Hymie Weiss’s brother in law, outside of the Four Deuces, an establishment run by South Side leaders Johnny Torrio and Al Capone. The car that police seized in the investigation belonged to Monahan, though he told police that Weiss was paying on the car for him. In Hot Springs, Arkansas at the time, receiving treatment for his headaches, Weiss was released of suspicion.
Some suspect that O’Banion was trying to frame Torrio and Capone for Duffy’s murder by meeting him outside The Four Deuces. However, it is more likely that was simply a way to get Duffy to meet him, as Duffy was believed to have ties to their gang. That fact and the fact that Weiss’s car was used, inadvertently throwing suspicion on O’Banion’s friend, implies that rather than being a plot to frame Torrio, it was another of O’Banion’s impulsive, spur of the moment decisions.
The Sieben Brewery Raid
When Prohibition had started it had been a free for all in Chicago, with everyone trying to steal alcohol and speakeasies from everyone else. Johnny Torrio, according to history, organized the gangs and got them to agree to only sell alcohol in their assigned territories. This had worked out remarkably well, except that The Terrible Genna Brothers, as they were known, a family gang of ruthless killers from the west side of the city refused to back off of O’Banion’s territory. And by May of 1924, O’Banion had had enough, deciding to cut ties with Torrio and the whole situation entirely. Unfortunately, he chose the worst possible way to do it.
Telling Johnny Torrio that he was interested in selling his stock in the Sieben Brewery O’Banion asked him to meet at the brewery to finalize the deal. What Torrio didn’t know but Dean O’Banion did was that on that particular day the brewery was set to be raided by the police. Torrio had already been arrested for violating prohibition once, but O’Banion had not, meaning that he would more than likely get off with a warning, while Torrio was going to have to serve jail time.
Making matters worse, O’Banion didn’t hide that he had been expecting the raid well, shaking hands with the police and in general being in quite a good mood for someone being arrested. It didn’t take much for Torrio to put together what had happened.
When the Genna Brothers found out, they demanded permission to kill O’Banion. The only person stopping them was the leader of Sicilian Union in Chicago, Mike Merlo, who was against violence and urged them not to get revenge. The Gennas and Torrio with their heavy respect for Merlo, agreed. Except it was really just waiting. Merlo was dying of cancer and once he died, there would be nothing standing in their way.
Let the War Begin
Over the summer of 1924, O’Banion was busy as ever. In July he was arrested for violating the Volstead Act again, this time with Hymie Weiss and another gangster, Dan McCarthy. Their trial was put on hold however, as Weiss was too ill to go to court and doctors informed authorities that they weren’t sure Weiss would live long enough to stand trial.
After the second arrest, O’Banion took a brief vacation out west, where he was introduced to a new weapon. The Thompson Submachine Gun. He was extremely interested in them and brought them back with him when he and his wife returned to Chicago.
November 9, 1924, Mike Merlo succumbed to cancer and took with him the stay of execution that he had given O’Banion. The Gennas brought in a hired gun and placed orders for thousands of dollars’ worth of flowers. In spite of them being rivals this was not unusual, Schofield’s was the place to go for your flower order, especially if you were part of the Underworld. That night, after O’Banion had left the shop Jim Genna and another man came in, getting a feel for the shop and picking up $1,000 of the $3,000 worth of flowers they had order from Mr. Schofield, telling him they would get the rest in the morning.
When the car pulled up on the day of the funeral to pick up the order, four men emerged from the car. Frankie Yale, John Scalise, Angelo Genna and Salvatore Ammatuna walked into the shop. According to William Crutchfield who was working that day, sweeping up fallen petals, O’Banion recognized them and asked William to go to the back so he could speak with them. O’Banion didn’t seem suspicious according to him. In fact, he greeted them with an outstretched hand. That was his view as the door to the back room closed behind him. And only a few moments later he heard gunshots. Dean O’Banion had been shot four times and lie dead on the floor of his beloved flower shop. And all hell was about to break loose.
Crutchfield telephoned the authorities who arrived at the shop, with sirens on and began their investigation. Coming down the street, Hymie Weiss and George Moran saw the cars and detoured to Weiss’s mothers house, where he telephoned the shop asking for O’Banion. He was informed of what had happened, and according to Rose Keefe in her book, The Man Who Got Away, silently went into the bathroom and locked the door. Moran had to break it down and when he did he found Weiss sobbing, saying “Everything I have in the world is gone.”
Saying Goodbye
O’Banion’s funeral was the biggest that Chicago had ever seen and it enthralled and disgusted people in equal measure. The funeral itself was attended by many figures of gangland and Torrio and Capone paid their respects as well. A bold move, considering it was generally accepted that they had helped with, if not entirely ordered the hit on the man for whom the funeral was being held. Vincent Drucci and Hymie Weiss cried openly and Weiss was photographed helped Viola, Dean’s widow, after being unable to carry the casket due to his grief.
After the funeral, as the last of the mourners filed out and the gangsters got into their cars and drove away, everyone knew this was not going to end well. Chicago held it’s breathe. The Chicago Beer Wars had begun.
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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.
Dean Charles O’Banion. (n.d.). https://www.myalcaponemuseum.com/id158.htm
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.
