On October 11, 1926, Chicago was experiencing a normal autumn day. The sky was overcast, the wind coming off the lake made the crisp breeze feel even cooler and at four o’clock on State Street, the sun was already getting low enough in the sky to remind everyone that before long it would be dark at five. When a Cadillac pulled up outside Holy Name Cathedral, no one on the street thought anything of it. The five men getting out of the car certainly didn’t expect anything out of the ordinary.
Out of the car stepped attorney, W.W. O’Brien, his assistant, Benjamin Jacobs, the driver and bodyguard, Sam Pellar, a gangster named Paddy Murray and the head of the Northside Gang, Earl J. Weiss, known to the papers as “Hymie” Weiss. Weiss was in a good mood as he started to cross the street, making his way to his office above Schofield’s Flower Shop where he and before him, his best friend and mentor, Dean O’Banion had run the Northsider’s operations. But half way there, the peaceful, ordinary afternoon was shattered, the sound of machine guns tearing through the air as, from a nearby window, Capone gunmen open fired.
Paddy Murray died instantly, O’Brien, Jacobs, and Peller were all hit but survived. Weiss, the target of the attack, somehow managed to initially survive the seven gun shot wounds, one of which pierced his skull. He was rushed to the hospital but died on the way. He left behind his mother, father, two brothers and a sister, a girlfriend and countless friends. He also left behind control of the Northside gang but he would not have been surprised.
Earl J. Weiss had essentially baited Capone, between his attack on him as the Hawthorne Hotel and then again at the peace talks a few days later, where, insulted by Capone’s insistence that everything could be made better with power, territory, and money, and his refusal to hand over the two remaining killers of O’Banion, he told him there would never be peace and stormed out. He then proceeded to buy his girlfriend and her mother an apartment and fully furnish it, he re-examined his will, he settled certain accounts, and tried to behave outwardly normal. Or as normal as one can when they know they are running out of time.
In 1924, Weiss had been diagnosed with something, usually credited as arterial cancer, though his symptoms bare a striking resemblance to systemic tuberculosis, made worse by heart trouble inherited through his family history. For years, he had suffered debilitating migraines, fainting spells, and, in at least one case, a seizure. Whatever it was, it was terminal. He would have had somewhere around two years to live, if he was lucky. Or stubborn. By the way, other words for stubborn are willful and resilient. All three of those words don’t really encompass the sheer willpower of Earl J. Weiss. Because since he was a child, life had thrown everything it had at him and he had stood back up and kept going, the chip on his shoulder getting bigger and bigger.
Born as Henryk Wojciechowski January 25, 1898 in Chicago, Illinois to Mary and William, he was the youngest of six siblings. Joe, born in 1889 the oldest and then Bruno, in 1890 were born in New York. The family moved to Chicago shortly after Bruno’s birth and then in 1894, Mary gave birth to twins, Filix (who would, before long, become Fred) and Walter. The exact date is unknown but between 1894 and 1900, Walter passed away as Mary answered the census taker saying she had given birth to six children but only five were living. In 1896, the family’s only daughter, Walerya (soon to be known as Violet) was born. And then, two years later, the final baby arrived.
William Weiss ran a saloon on Division Street and Mary ran one on Austin Avenue, next door to where the family lived. Earl would have lived with his mother on Austin, though, likely he traveled to the saloon on Division as well and, as most children in his neighborhood did, everywhere in between. He grew up around the saloon patrons and while most of them were likely not on the wrong side of the law, several most likely were. By all accounts, Earl was extremely intelligent, even as an adult he was considered to have a brilliant mind, loved reading, discussing history and religion, and in his pocket he would always carry a bible that had been given to him as a child.
Growing up in the environment he did, with an ill tempered and mostly absent father, it’s no wonder he was a little jaded, but then at the end of 1912, his oldest brother Joe was arrested after shooting and killing a man, in an attempt to defend another man in his father’s saloon. He was acquitted in 1913, but Joseph Weiss, who had been suffering from pulmonary tuberculosis found his condition severely worsened from the stress and moved to a hospital in New Mexico for treatment where he died just days before Christmas that same year. The effect on fifteen year old Earl must have been immense, not just watching his brother go through a trial for murder and the stress his family would have gone through as well as the grief of losing him and how it would have devastated his already struggling family.
Tragedy struck the family again in 1916 when on January 25, Violet gave birth a month early to a still born baby boy at the house she shared with her husband, Philip Monahan, and her mother, Mary.
There isn’t evidence of Earl being arrested before the year 1918. His brother, Fred, on the other hand, was arrested at least twice, once for robbing a post office in 1917 and another for stealing cars in February of 1918. Shortly after his arrest, before anything could come of it, he was drafted into World War I.
All the while, Earl was working as a truck driver for the Seiban Breweries. What would have happened had he not been denied by the draft board for what they deemed to be a weak heart (he would never agree with them, thinking it shouldn’t have mattered) and he had followed his brother to war, we will never know. What did happen was that Earl J. Weiss, stayed in Chicago and at twenty years old and had faced more than enough hardship to bring much older men to their knees. Instead, he made the acquaintance of one Dean O’Banion and O’Banion’s mentor, Charles Reiser, who taught them the art of safe blowing, which Weiss suited to exact amounts and organization and being of a meticulous nature, was far more natural at than his new friend (Dean O’Banion once managed to blow the wall off a bank and leave the vault unharmed).
Weiss and O’Banion were a study in opposites. O’Banion was naturally impulsive at all times, jovial, friendly, and naturally charismatic. Weiss was, by nature, quieter and more thoughtful, unless provoked. O’Banion was smart, but not quite the same way Earl was, O’Banoin didn’t have the patience for learning that that the other had or the self control to not come in headfirst without thinking of the consequences. But they were natural business partners and the best of friends. Earl adored Dean and the feeling was mutual (though one can imagine the internal screaming when Dean decided to shoot Davey Miller in public for a perceived insult).
The two found great success in bootlegging. Dean, with his shares of the flower shop and his work with the flowers and customers was happy to run the more adventurous and outwardly visible aspects of the enterprise, while Weiss was in charge of the actual business parts of it. Their two friends Victor D’Ambrosio alias Vincent Drucci and George Moran rounded out the quartet that ran the Northside Gang.
But in 1924, after a hundred insults and arguments with the Genna Gang and a lack of help from Johnny Torrio who was supposed to be making sure everyone stayed in their territory, The Northsider’s decided to put an end to their alliance with the other gangs and double crossed Torrio in the Sieban Brewery Raid. The plan was most likely Earl’s and so in November when Torrio okayed the murder of O’Banion, he felt not only an immense sense of loss but guilt as well. He collapsed in his mother’s bathroom and George Moran remembered him saying “All I have in the world is gone.”
A few days later, he seemed to have recovered something of his defiance, when, while being questioned about his friend’s murder, he was asked by Detective Shoemaker of the Chicago Police, “If you knew anything about this case would you tell me?”
Weiss looked at him and shook his head. “To be perfectly frank, I guess I wouldn’t.” Weiss even refrained from causing a scene at the funeral when Torrio and Al Capone showed up. It wasn’t until January 24, 1925, that they attempted to murder Torrio in front of his house as revenge for Dean’s death.
It was a plan that was actually going well. Weiss and Moran waited for Anna Torrio, the Outfit’s boss, to be safely out of the way with their dog, before firing on him and as Moran ran up to fire a final shot, his gun jammed as a laundry truck turned the corner, causing Drucci to honk and the Northsiders to flee and giving Torrio his chance of survival. His wife saved his life, not once but twice, by giving strict instructions at the hospital that no one was allowed in except family. And it was a wonderful initiative because, in a burst of uncharacteristic impulsivity, Earl Weiss turned up at the hospital asking to visit him, with a car full of gangsters outside. The nurse told him to leave and threatened to call the cops. Swearing, he left.
In May of that year, Weiss was imprisoned in McHenry County jail, though he still ran the Northside Gang from his cell. And for the next year and a half he would build it up into a bigger and better business with contacts all over the country.
For a year and a half, and through the Hawthorne attack and the peace talks, all the way up to his death, Earl J. Weiss, kept picking himself up and pushed forward with an outward determination that most people will never be able to possess. He managed to add six months to his prognosis and it’s probable he could have added even more; he certainly wasn’t going to let illness take him out. And it’s why even after seven gunshot wounds, at least one of which would have been instantly fatal to anyone else, he held on to life for just a little bit longer.
Except even he, as stubborn as he was, would have been getting tired of fighting and wanted a rest. On the way to the hospital, one hundred years ago today, Earl J. Weiss, finally, finally, finally, stopped fighting his way forward and let himself rest.
Binder, J. J. (2017). Al Capone’s beer wars : a complete history of organized crime in Chicago during prohibition. Prometheus Books.
Chicago Tribune. (1926, October 12). Hymie Weiss Slain. Chicago Tribune, 1. https://www.newspapers.com/image/355134658/
Chicago history museum. (2017). Chicago History Museum. https://www.chicagohistory.org/
Hymie Weiss. (n.d.). Www.Myalcaponemuseum.Com. Retrieved September 20, 2026, from https://www.myalcaponemuseum.com/id89.htm
Keefe, R. (2003). Guns and Roses. Turner Publishing Company.
Keefe, R. (2005). The Man who Got Away The Bugs Moran Story : a Biography. Cumberland House Publishing.
National Archives. (2024). National archives. Archives.Gov. https://www.archives.gov/

