The St Valentines Day Massacre
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On the morning of February 14, 1929, a horrific crime took place on the north side of Chicago. Several men were lined up against the wall of an auto garage and gunned down in cold blood by machine gun fire. The event marked a low point in the violent mob wars that took place in the city of Chicago. It also marked a turning point in attitudes towards the 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. This episode is sponsored by Quince. I don't think most people would consider me the most stylish guy. I don't really see the point in spending a ton of money to try to be fashionable. But with Quince, I can get high-end versatile pieces at prices that I can actually afford. All Quince items are priced 50-80% less than similar brands.

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The St. Valentine's Day Massacre wasn't the worst event in the history of organized crime, but it has 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 of alcohol under the 18th Amendment, a.k.a. 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, and the first was known as the Chicago Outfit.

The Chicago outfit rose to power during the early 20th century, fueled by opportunities created by Prohibition and the city's deeply entrenched corruption. Its origins trace back to the Italian-American crime 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 would cost him his life.

In 1920, Colosimo 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 Northside Gang led by Dean O'Banion, the other gang in this story. The Northside Gang emerged from 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, just like the Chicago Outfit.

Led by O'Banion, the Northside gang quickly expanded its bootlegging operations, securing key smuggling routes and forming alliances with breweries and speakeasies on the city's north side. Unlike their rivals in the Chicago outfit, who were predominantly Italian-American, the Northsiders consisted mostly of Irish and German immigrants, 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 Northside gang and the Chicago outfit escalated as both sides 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 Northside 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 Northside gang fell under the leadership of a new boss, Jaime Weiss. After taking control of the Northside gang, Weiss launched an all-out war against Al 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 Northside gang's headquarters near Holy Name Cathedral. His death left the gang in turmoil, paving the way for the rise of yet another new boss, Bugs Moran. Under Bugs Moran, the gang remained a powerful force, engaging in assassination attempts, hijackings, and shootouts to maintain its foothold in Chicago.

And this was the environment in Chicago as of early 1929. Rival gangs, assassinations, violence, and a whole lot of bootlegging money that was up for grabs. On the morning of February 29th, 1929, at around 1030 a.m., seven men affiliated with the Northside gang gathered inside the garage at 2122 North Clark Street in Chicago. The garage, which was 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, so nobody suspected that they were walking into a deadly trap.

The seven men that were there were Peter and Frank Gusenberg, who were Northside gang enforcers, Albert Katchelek, Moran's second-in-command, Adam Heyer, a Northside gang bookkeeper and business manager, Reinhard Schwimmer, a gang associate and optometrist, John May, a gang mechanic who actually wasn't believed to be a criminal, and Albert Weinschenk, a gang associate mistaken for Bugs Moran.

Suddenly, a black Cadillac resembling a police car pulled up outside of the garage. Witnesses saw five men step out. Two of them were dressed in Chicago police uniforms, while the others were wearing civilian clothes. 21 watching from the outside, it appeared to be a law enforcement raid. The men in uniforms enter the garage first, barking orders at the gangsters inside, demanding that they line up against the back wall.

Believing that they were simply being arrested, the gangsters complied without resistance, assuming that they could bribe their way out of trouble as they've done many times before. With the victims standing defenseless against a brick wall, the supposed officers suddenly pulled out Thompson's 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 the bodies, leaving them slumped over, soaked in blood.

To ensure that no one 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 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 their fake police car.

The ruse was designed to fool any witnesses into thinking that a legitimate police raid had taken place, preventing any immediate suspicion of foul play. Minutes later, however, the real police arrived to find a horrific scene. Six of the seven men were dead, their bodies riddled with bullets. But 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 and dying. 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 Bugs 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, indeed, 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, quote, 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 for the massacre 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 involved in investigating organized crime, particularly focusing on Al Capone. Unable to convict him for murder, authorities shifted their strategy and federal agents, led by Elliot 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.

Although the massacre failed to kill Bugs Moran, it decimated the Northside gang, leaving it weakened and unable to recover its former strength. It also solidified Al Capone's reputation as the most ruthless crime boss in America. Although ironically, the attention it brought to him 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 enterprises that it had enabled. The executive producer of Everything Everywhere Daily is Charles Daniel. The associate producers are Austin Okun and Cameron Kiefer.

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