On the cold morning of February 14, 1929, a gruesome event unfolded that shocked Chicago and the entire nation. Known as the St. Valentine’s Day Massacre, the killing of seven members of the North Side Gang was the climax of Chicago’s bloody Prohibition-era gang wars. This massacre, orchestrated by rivals of Al Capone, cemented the city’s reputation as the epicenter of organized crime and exposed the inability of local law enforcement to control gang violence.
The Battle for Bootlegging Supremacy
During the 1920s, Prohibition made the sale of alcohol illegal, creating a massive black market that gangs fought ruthlessly to control.
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Al Capone’s Outfit dominated the South Side of Chicago, running breweries, speakeasies, and gambling dens.
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George “Bugs” Moran’s North Side Gang held strong influence in the North Side neighborhoods.
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Both gangs fought for territory and distribution networks, resulting in bombings, assassinations, and street battles.
By 1929, Capone’s Outfit had gained the upper hand, but Moran remained one of the last powerful rivals standing in his way.
The Setup
On Valentine’s Day morning, Moran’s men gathered at the S.M.C. Cartage Company garage on North Clark Street. They believed they were meeting bootleggers with a shipment of smuggled liquor.
Unknown to them, it was a deadly trap:
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Four men, at least two dressed as Chicago police officers, entered the garage.
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The fake police ordered Moran’s men to line up against the wall.
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Believing it was a routine raid, the gangsters complied without resistance.
At that moment, the disguised men opened fire with Thompson submachine guns, unleashing over 70 rounds of bullets.
The Victims
Seven men were killed in the massacre:
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Peter Gusenberg – Moran’s enforcer
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Frank Gusenberg – Peter’s brother, who lived long enough to refuse to name his attackers
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Albert Kachellek – gang associate
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Adam Heyer – gang bookkeeper
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Reinhardt Schwimmer – optometrist associated with the gang
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Albert Weinshank – business owner and Moran associate
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John May – a mechanic who worked for the gang
Their bodies, riddled with bullets, created one of the most chilling crime scenes in American history.
Who Was Responsible?
Although Al Capone was the prime suspect, he had carefully crafted an alibi—he was in Florida at the time.
The massacre was likely planned by Capone’s trusted lieutenant, Jack “Machine Gun” McGurn, who sought to eliminate Moran once and for all.
Ironically, Moran himself escaped because he was late to the meeting. Upon hearing the gunfire from a nearby café, he fled, remarking later:
“Only Capone kills like that.”
Public Reaction
The massacre horrified Chicago and the nation.
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The sheer brutality, with victims gunned down execution-style, shocked even hardened Chicagoans accustomed to gang violence.
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Newspapers ran front-page photographs of the bodies, creating a public relations disaster for Capone.
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Ordinary citizens began demanding that law enforcement take serious action against organized crime.
The event also revealed the deep corruption in the Chicago Police Department. Many suspected that real police may have assisted in the massacre or at least looked the other way.
Law Enforcement’s Response
Despite public outrage, no one was ever convicted for the St. Valentine’s Day Massacre.
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Witnesses were too afraid to testify.
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The crime scene had been contaminated, making forensic evidence unreliable.
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Corrupt officials ensured that investigations stalled.
The massacre, however, pushed the federal government to intensify its fight against organized crime. President Herbert Hoover ordered federal agencies to target Capone, eventually leading to his conviction for tax evasion in 1931.
Legacy of the Massacre
The St. Valentine’s Day Massacre became a defining moment in American criminal history:
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It highlighted the extreme violence of Prohibition-era Chicago.
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It symbolized the failure of local law enforcement, riddled with corruption and intimidation.
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It fueled the myth of Al Capone as a ruthless yet untouchable gangster.
Today, the site of the garage where the massacre took place is a parking lot, but the story continues to haunt Chicago’s past.
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