The St. Valentine’s Day Massacre, which occurred on February 14, 1929, in Chicago, is one of the most notorious events in organized crime history. The massacre involved the murder of seven members of the North Side Gang, led by George “Bugs” Moran, and is widely believed to have been orchestrated by rival gang leader Al Capone. On that day, members of Capone’s gang, disguised as police officers, entered a garage at 2122 North Clark Street, where Moran’s gang was gathered. The assailants lined the victims against a wall and opened fire with Tommy guns, killing seven men in a matter of seconds. The brutality of the attack shocked the nation and highlighted the violent turf wars between Chicago’s organized crime factions during the Prohibition era. While Capone was widely suspected of orchestrating the massacre, he denied any involvement and claimed to be in Florida at the time of the killings. The lack of concrete evidence linking him directly to the crime allowed him to evade prosecution. The massacre intensified law enforcement efforts to combat organized crime in Chicago, but it also solidified Capone’s reputation as a powerful and ruthless mobster.