When Al Capone's Henchmen Marked Valentine's Day With a Bloody Massacre

Instead of romance, Valentine’s Day in Chicago was filled with bloodshed in 1929, when the massacre of seven mobsters associated with George “Bugs” Moran marked the culmination of a violent gang war that defined an era in the city’s history.

The origins of the killings now known as the St. Valentine’s Day Massacre date back to the ratification of the 18th Amendment in 1919. Marking the beginning of Prohibition, the amendment outlawed the manufacture, transportation and sale of alcohol in the United States as of January 17, 1920.

It also created a fierce black-market industry of bootleggers. Mobsters smuggled foreign-made liquor from Canada and Mexico and built shipping networks of rum runners—individuals who traveled abroad by sea to bring back illegal booze. Others turned to bathtub distillery operations, creating gin and other liquors at home.

In Chicago, as in other major cities, a few high-profile mobsters battled it out for bootlegging supremacy. Al Capone, sometimes known as “Scarface,” led a gang of racketeers that essentially turned neighborhoods in the Windy City into a fiefdom for their leader. Capone harbored visions of dominating Chicago and the entire Midwest, and his gun-toting followers often resorted to violence to defend that goal.

This situation didn’t bode well for Moran, Capone’s counterpart within another Chicago gang. Moran was the head of the North Side Gang, a rival bootlegging outfit, and Capone and Moran often traded blows—and gunfire—in the name of liquor distribution.

This rivalry came to a head on February 14, 1929. Moran’s mob was expecting a delivery of whiskey at its headquarters, a commercial garage at 2122 North Clark Street. Capone was holed up in Florida at the time but is believed to have sent four assassins to take out Moran and his operatives.

St. Valentine's Day Massacre Explained (Al Capone, Bugs Moran)

At 10:30 a.m. on Valentine’s Day, the assassins entered the garage and took Moran’s unarmed men by surprise. They lined up the seven men on the back wall of the garage, then shot them with submachine guns. The dead included brothers Peter and Frank Gusenberg, Albert Kachellek, Adam Heyer, Reinhardt Schwimmer, Albert Weinshank, and John May. The exact identities of the assailants, two of whom were wearing police uniforms, remains unknown. Officials maintain that they were likely hitmen sent by Capone.

Moran dodged execution that morning. Though the massacre could have sparked an even larger turf war between Scarface and Bugs, it largely marked the rivalry’s end. Capone was jailed in 1931, and Moran soon lost control over his territory. He died in prison in 1957.

Had the St. Valentine’s Day massacre not neutered most of Moran’s bootlegging operation, the end of Prohibition in 1933 would have quickly rendered it unnecessary.

But the particularly brutal shootings have continued to captivate a wide audience. Mobsters like Capone and Moran have been romanticized in popular culture, and the still-unsolved crime has invited amateur sleuths to study up.

The actual site of the massacre, however, has been relegated to history books. The garage was briefly turned into an antique furniture business and became an unofficial tourist destination for true crime fanatics. That business failed, and the building at 2122 North Clark Street was later demolished. Its back brick wall, covered in blood stains and damaged by bullets, has since traveled the continent in search of a final resting place. The majority of its 414 bricks are now on display in Las Vegas’ Mob Museum.