On the morning of 14 February 1929, Chicago witnessed one of the most notorious gangland killings in American history. Seven men were lined up against a brick wall and gunned down in a garage at 2122 North Clark Street. The St. Valentine’s Day Massacre, as it came to be known, marked the bloody climax of Chicago’s beer wars and forever changed the public’s perception of organised crime in America.
The players
Al Capone’s South Side Gang
At the heart of this brutal episode was Al “Scarface” Capone, Chicago’s most powerful gangster. Having risen through the ranks of Johnny Torrio’s criminal empire, Capone controlled the South Side with an iron fist. His organisation pulled in millions from bootlegging, gambling, and prostitution, but Capone wanted more.
George “Bugs” Moran’s North Side Gang
The North Side belonged to George “Bugs” Moran, who had inherited the territory from Dean O’Banion and Hymie Weiss – both previous leaders gunned down in the ongoing turf war. Moran’s gang, predominantly Irish-American, stood as the last major obstacle to Capone’s complete domination of Chicago’s underworld.
The build-up
The rivalry between Chicago’s North and South Side gangs had been escalating for years. Each side conducted bloody raids on the other’s territories, hijacked liquor shipments, and murdered rival gang members. By early 1929, the situation had reached a boiling point.
Moran’s gang had repeatedly attempted to assassinate Capone and his associates. They machine-gunned Capone’s headquarters at the Hawthorne Inn and killed several of his top lieutenants. Capone, who usually responded swiftly to such provocations, began planning what would become his most infamous retaliation.
The Massacre
The plan was cunning in its simplicity. Capone’s men contacted Moran, offering to sell him a hijacked shipment of Canadian whiskey at an irresistible price. The delivery was set for 10:30am on Valentine’s Day at the SMC Cartage Company garage, a Moran-owned business.
As Moran’s men gathered at the garage that morning, two police cars pulled up outside. Four men – two in police uniforms and two in civilian clothes – entered the garage. Believing it to be a routine police raid, Moran’s men complied when ordered to face the wall. What happened next would shock the nation.
The disguised gunmen produced Thompson submachine (Tommy) guns and opened fire. Seven men were killed:
- Peter Gusenberg
- Frank Gusenberg
- Albert Kachellek (alias James Clark)
- Adam Heyer
- Reinhardt Schwimmer
- Albert Weinshank
- John May
Ironically, the massacre’s primary target, “Bugs” Moran, was not among the victims. He had been approaching the garage when he spotted what he thought were police officers and decided to keep walking.
The aftermath
The brutality of the Valentine’s Day Massacre shocked the American public and marked a turning point in the way organised crime was perceived and combated.
The massacre’s aftermath rippled through law enforcement, fundamentally transforming how America fought organised crime. Local police, embarrassed by their inability to contain gang violence, found themselves under intense scrutiny. This pressure catalysed the creation of the nation’s first crime laboratory, where investigators could finally apply scientific methods to criminal investigations.
The FBI, which had previously maintained a hands-off approach to gang activity, began to take a more active role in combating organised crime, setting the stage for the more aggressive federal response to criminal organisations that would define the coming decades.
The political landscape shifted dramatically in the wake of the killings. Chicago’s politicians, many of whom had turned a blind eye to gang activities in exchange for bribes and electoral support, could no longer ignore the violence plaguing their city. Public outrage forced them to allocate more resources to fighting organised crime, while newspapers nationwide began questioning the wisdom of Prohibition itself. The sight of seven bodies on a garage floor became a powerful argument for ending the “noble experiment” that had given rise to such powerful criminal enterprises.
Within the criminal underworld, the massacre marked both an apex and a turning point. Capone’s brutal efficiency in eliminating rivals had backfired, transforming him from a somewhat romanticised Robin Hood figure into a public enemy. The North Side Gang, already weakened by years of warfare, never recovered from losing so many key members. More significantly, the massacre’s brutality changed the rules of engagement among criminal organisations. The era of open warfare on city streets began to fade as criminal enterprises recognised the need for a more subtle approach to their operations.
Capone’s downfall
Though never charged for the massacre, Capone’s organisation began to crumble under increased law enforcement scrutiny. In 1931, he was convicted of tax evasion and sentenced to 11 years in federal prison, effectively ending his reign as Chicago’s crime boss.
Historical legacy
The St. Valentine’s Day Massacre remains one of the most infamous episodes in American criminal history. The garage where the killings took place became a macabre tourist attraction until its demolition in 1967. Today, the bullets-scarred bricks from the wall are displayed at The Mob Museum in Las Vegas.
The massacre represented both the apex and the beginning of the end for the brazen gang violence of the Prohibition era. It demonstrated the devastating consequences of America’s failed experiment with Prohibition and served as a catalyst for changes in how the nation approached organised crime.
The event continues to captivate the public imagination and is featured in countless books, films, and documentaries. It stands as a stark reminder of a tumultuous period in American history when criminal organisations operated with near impunity and violence ruled the streets of Chicago.
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