The St. Valentines Day Massacre

Podcast Transcript

On the morning of February 14, 1929, a horrific crime took place on the north side of Chicago.

Seven men were lined up against the wall of an auto garage and gunned down in cold blood by machine gun fire.

The event marked the low point of the violent mob wars that took place in the city of Chicago. It also marked a turning point in attitudes towards prohibition in the United States and the war on organized crime.

Learn more about the St. Valentine’s Day Massacre, why it happened, and its repercussions on this episode of Everything Everywhere Daily.

The St. Valentine’s Day Massacre wasn’t the worst event in the history of organized crime, but it has had an outsized place in the American psyche.

Part of this has to do with the day it took place, the subsequent name it was given, and the parties involved.

However, part of its fame can also be credited to what happened after the event and how it ended up shaping history.

Before the St. Valentine’s Day Massacre, Chicago was a city dominated by organized crime, rampant corruption, and Prohibition-fueled violence. The 1920s often called the Roaring Twenties, saw an explosion of illicit activities due to the nationwide ban on alcohol under the 18th Amendment, aka Prohibition.

This era turned Chicago into a battlefield for rival gangs, with bootlegging, gambling, and extortion driving an underground economy.

The 1919 Volstead Act made it illegal to manufacture, sell, or transport alcoholic beverages, but demand for liquor remained high. Criminal organizations saw a massive business opportunity, leading to the rise of powerful gangsters who controlled speakeasies, distilleries, and distribution networks.

There were two rival organizations that came to prominence in Chicago during this period. The first was the Chicago Outfit.

The Chicago Outfit rose to power during the early 20th century, fueled by the opportunities created by Prohibition and the city’s deeply entrenched corruption. Its origins trace back to the Italian-American criminal syndicates that operated in Chicago’s underworld before World War I.

Under the leadership of Big Jim Colosimo, the Outfit initially focused on the typical gambling, prostitution, and extortion. However, Colosimo was resistant to entering the bootlegging business when Prohibition began, a decision that cost him his life.

In 1920, he was assassinated—allegedly on the orders of his protégé Johnny Torrio, who saw the immense financial potential in illegal alcohol distribution.

With Colosimo out of the way, Torrio expanded the Outfit’s operations and streamlined its bootlegging networks, turning it into a well-organized empire. His vision was not just about brute force but about running crime like a business, forming alliances, and monopolizing liquor distribution.

However, his control was challenged by rival gangs, particularly the North Side Gang led by Dean O’Banion, the other gang in this story.

The North Side Gang emerged in the early 20th century as one of Chicago’s most formidable organized crime groups, initially formed by Irish-American criminals involved in gambling, robbery, and extortion. Its rise to power also coincided with the advent of Prohibition like the Chicago Outfit.

Led by Dean O’Banion, the North Side Gang quickly expanded its bootlegging operations, securing key smuggling routes and forming alliances with breweries and speakeasies in the city’s North Side.

Unlike their rivals in the Chicago Outfit, who were predominantly Italian-American, the North Siders consisted mostly of Irish and German-Americans, giving them a distinct identity in the city’s criminal underworld. O’Banion was known for his charismatic but ruthless leadership, and he cultivated relationships with corrupt law enforcement officials while aggressively expanding his territory.

Tensions between the North Side Gang and the Chicago Outfit escalated as both sought dominance over the bootlegging trade. The rivalry became deadly when O’Banion tricked Johnny Torrio, the leader of the Outfit, into purchasing a brewery that was about to be raided by federal agents. This betrayal led to O’Banion’s assassination in 1924, a hit orchestrated by Torrio.

After O’Banion’s murder, the retaliation from the North Side Gang left Torrio seriously wounded. Seeing the writing on the wall, Torrio retired to Italy, leaving the Chicago Outfit in the hands of his young, ambitious lieutenant—Al Capone.

Under Capone’s rule, the Outfit reached its peak, operating with a mix of ruthless violence and calculated business acumen. Capone expanded the Outfit’s influence beyond bootlegging, controlling speakeasies, brothels, gambling dens, and political figures. He was both feared and admired, presenting himself as a businessman while ordering assassinations to eliminate rivals.

After the death of O’Banion, the North Side Gang fell under the leadership of the a boss Hymie Weiss.

After taking control of the North Side Gang, Weiss launched an all-out war against Capone, orchestrating multiple assassination attempts, including a 1926 ambush on Capone at the Hawthorne Hotel, which riddled the building with bullets but failed to kill him.

In retaliation, Capone ordered Weiss’s execution, and on October 11, 1926, Weiss was gunned down in a hail of bullets outside the North Side Gang’s headquarters near Holy Name Cathedral.

His death left the gang in turmoil, paving the way for the rise of Bugs Moran.

Under Bugs Moran, the gang remained a powerful force, engaging in assassination attempts, hijackings, and shootouts to maintain its foothold in Chicago.

This was the environment in Chicago in early1929. Rival gangs, assassinations, violence, and a whole lot of bootlegging money that was up for grabs.

On the morning of February 14, 1929, at around 10:30 AM, seven men affiliated with the North Side Gang gathered inside the garage at 2122 North Clark Street in Chicago.

The garage, owned by “Bugs” Moran, served as a hub for his bootlegging operations. That morning, the men were expecting a large shipment of illegal whiskey, a routine part of their business. The atmosphere was business as usual—no one suspected they were walking into a deadly trap.

The seven men were:

Peter and Frank Gusenberg, North Side Gang enforcers
Albert Kachellek, Moran’s second-in-command
Adam Heyer, a North Side Gang bookkeeper and business manager
Reinhardt Schwimmer, a gang associate and optometrist
John May, a gang mechanic who was not believed to be a criminal
Albert Weinshank, a gang associate mistaken for Bugs Moran

Suddenly, a black Cadillac resembling a police car pulled up outside the garage. Witnesses saw five men step out—two of them were dressed in Chicago police uniforms, while the others were wearing civilian clothes.

To anyone watching, it appeared to be a law enforcement raid. The men in uniforms entered the garage first, barking orders at the gangsters inside, demanding that they line up against the back wall. Believing they were simply being arrested, the gangsters complied without resistance, assuming they could bribe their way out of trouble as they had done many times before.

With the victims standing defenseless against the brick wall, the supposed officers suddenly pulled out Thompson submachine guns and opened fire. The gunmen unleashed a brutal volley of bullets, firing over 70 rounds into their targets. The force of the attack shredded their bodies, leaving them slumped over, soaked in blood.

To ensure that none survived, the killers walked up and delivered finishing shots at point-blank range. When the shooting stopped, the garage was eerily silent, filled only with the acrid scent of gunpowder and the sight of lifeless bodies sprawled in pools of blood.

In a final deceptive move, the uniformed gunmen marched their civilian-dressed accomplices out at gunpoint as if making arrests before calmly driving away in the fake police car. The ruse was designed to fool any witnesses into thinking that a legitimate police raid had taken place, preventing immediate suspicion of foul play.

Minutes later, the real police arrived to find a horrific scene. Six of the seven men were dead, their bodies riddled with bullets, while one man, Frank Gusenberg, was still clinging to life despite being shot 14 times. When the police questioned him about who was responsible, he refused to name his attackers, uttering only the words “Nobody shot me” before succumbing to his wounds shortly after.

By sheer luck, Bugs Moran himself had avoided the massacre. He had been running late that morning and, upon seeing the fake police officers enter the garage, decided to wait outside. When the gunfire erupted, he quickly fled the scene, unknowingly escaping an assassination attempt that had been planned specifically for him.

The massacre, while failing to kill Moran, effectively wiped out his top enforcers and severely weakened his gang, allowing Al Capone to assert near-total control over Chicago’s criminal underworld.

The aftermath of the St. Valentine’s Day Massacre sent shockwaves through Chicago and the entire nation. The sheer brutality of the killings—seven men lined up and executed in cold blood—was unlike anything the public had seen before, even in a city notorious for gang violence.

While organized crime had long been an open secret, the massacre exposed its merciless nature in a way that was impossible to ignore. The image of the blood-soaked garage, captured in crime scene photos and published in newspapers across the country, horrified the public and turned sentiment against the unchecked violence of the Prohibition era.

Although Al Capone was widely suspected of orchestrating the attack, he was never directly charged. At the time of the massacre, he was in Florida, providing him with a convenient alibi. His rival, Bugs Moran, immediately blamed Capone, stating, “Only Capone kills like that.”

However, without any surviving witnesses or concrete evidence linking Capone to the crime, law enforcement was unable to prosecute him for the killings. Even Frank Gusenberg, the only victim who briefly survived, refused to identify his attackers before dying from his injuries. The lack of convictions only deepened public frustration with law enforcement’s inability to control organized crime.

The massacre also placed immense pressure on politicians and law enforcement to take stronger action against Chicago’s rampant gang violence. The city’s police force, which was notoriously corrupt and often in the pockets of gangsters, faced public scrutiny. As a result, the federal government became more involved in investigating organized crime, particularly focusing on Capone.

Unable to convict him for murder, authorities shifted their strategy, and federal agents, led by Eliot Ness and the Treasury Department, began pursuing Capone for tax evasion. This shift in approach eventually led to Capone’s conviction in 1931, marking the beginning of the downfall of the Chicago Outfit’s open dominance.

More broadly, the massacre intensified calls for the end of Prohibition, as many Americans began to see it as the root cause of the gang wars.

Prohibition had made criminals rich and powerful while turning cities into battlegrounds. In the years that followed, momentum grew for Repeal, and by 1933, the 18th Amendment was overturned, effectively dismantling the lucrative bootlegging empire that had allowed gangsters like Capone and Moran to thrive.

Though the massacre failed to kill Bugs Moran, it decimated the North Side Gang, leaving it weakened and unable to recover its former strength. It also solidified Capone’s reputation as the most ruthless crime boss in America, though ironically, the attention it brought would contribute to his eventual downfall.

The St. Valentine’s Day Massacre became one of the defining moments of the Prohibition era, a symbol of unchecked criminal violence that ultimately led to increased government intervention and the dismantling of the criminal empires it had enabled.

The Executive Producer of Everything Everywhere Daily is Charles Daniel. The Associate Producers are Austin Oetken and Cameron Kieffer.

Today’s review comes from listener Banter with Boogs over on PodBean app. They write.

Hi Gary me and my mom have been listening to you since covid and are officially apart of the completion club. I was one of the people who was in the episode where people sent in voice recordings. you’ve taught us so much and definitely helped with some trivia nights.

Thanks, Boogs! I’d like to formally welcome you and your mom to the completionist club. I’m glad I’m able to help you out on your Trivia nights.

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