Today in History: Chicago's 'St. Valentine's Day Massacre'

Seven gang members were gunned down in a Chicago garage in 1929 in a notorious mob attack.

Published on Feb. 14, 2026

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On February 14, 1929, seven members of a rival gang were killed in a brutal attack in a Chicago garage, an event that became known as the 'St. Valentine's Day Massacre'. The victims were associates of Al Capone's criminal organization, and the attack was seen as a major event in the violent gang wars that plagued the city during the Prohibition era.

Why it matters

The 'St. Valentine's Day Massacre' was a pivotal moment in the history of organized crime in Chicago, highlighting the brutal violence that characterized the city's gang wars during the 1920s. The attack brought national attention to the power struggles between rival criminal organizations like Capone's and further cemented Chicago's reputation as a hub of gangster activity.

The details

On the morning of February 14, 1929, seven men associated with the North Side Gang, a rival of Al Capone's South Side organization, were lined up against a wall in a Chicago garage and gunned down by four men dressed as police officers. The victims included several high-ranking members of the North Side Gang, and the attack was seen as retaliation for the murder of one of Capone's top lieutenants the previous year.

  • The 'St. Valentine's Day Massacre' took place on February 14, 1929.
  • The attack occurred in a Chicago garage.

The players

Al Capone

A notorious Chicago gangster who led the South Side Gang and was involved in a violent rivalry with the North Side Gang.

North Side Gang

A criminal organization in Chicago that was rivals with Al Capone's South Side Gang.

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The takeaway

The 'St. Valentine's Day Massacre' exemplified the extreme violence and power struggles that defined the era of Prohibition in Chicago, as rival gangs fought for control of the lucrative bootlegging and racketeering industries. The attack cemented Chicago's reputation as a hub of organized crime and set the stage for further crackdowns on gangster activity in the city.