On February 14, 1929, Chicago’s streets were stained with blood in one of the most infamous incidents of the Prohibition era—the St. Valentine’s Day Massacre. Seven members and associates of the North Side Gang, a criminal outfit led by George “Bugs” Moran, were lined up against a wall in a garage on North Clark Street and executed in cold blood, allegedly on the orders of infamous mob boss Al Capone.
A Chilling Crime Scene
That morning, Moran’s men gathered at the SMC Cartage Company garage, likely expecting a shipment of bootleg liquor. Instead, four men—two dressed as police officers—stormed in. The impostors ordered the group to line up against the wall, as though it were a routine police raid. Moments later, the disguised gunmen opened fire with Thompson submachine guns, killing six instantly and leaving one, Frank Gusenberg, mortally wounded. Gusenberg refused to name his attackers, even as he lay dying.
The crime scene shocked law enforcement and the public. Photographs of the slain gangsters sprawled against the garage wall became iconic images of the Prohibition era, symbolizing the violent struggle for control of Chicago’s lucrative bootlegging operations.
Al Capone’s Shadow
Although Al Capone was in Florida at the time, many suspected he orchestrated the massacre to eliminate his rival, Bugs Moran. The massacre was the culmination of a brutal gang war between Capone’s South Side gang and Moran’s North Side operation, both vying for dominance in the illegal liquor trade.
Moran, who escaped the massacre by arriving late, publicly blamed Capone for the attack, saying, “Only Capone kills like that.” However, no one was ever convicted of the crime. Capone, while widely suspected, maintained plausible deniability and avoided legal repercussions for the massacre itself.
The Massacre’s Aftermath
The St. Valentine’s Day Massacre marked a turning point in America’s perception of organized crime. It highlighted the rampant violence and lawlessness of the Prohibition era, spurring calls for reform. While Capone’s empire continued to thrive for a few more years, the massacre brought increased federal attention to his activities. In 1931, he was convicted—not for murder, but for tax evasion—and sentenced to prison.
Moran, meanwhile, lost much of his influence and power after the massacre. His diminished gang never recovered its dominance in Chicago’s underworld.
Legacy of Violence
The St. Valentine’s Day Massacre remains one of the most notorious events in American crime history. It symbolizes the dark consequences of Prohibition, when illicit alcohol fueled violent power struggles among organized crime syndicates. The massacre also cemented Al Capone’s place in the annals of infamy, earning him a reputation as the quintessential gangster of the Roaring Twenties.
