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On the morning of Thursday, February 14, 1929, St. Valentine's Day, five members of the North Side Gang, plus gang collaborators Reinhardt H. Schwimmer and John May, were lined up against the rear inside wall of the garage at 2122 North Clark Street, in the Lincoln Park neighborhood of Chicago's North Side, and executed. The murders were committed by gangsters allegedly hired from outside the city by the Al Capone mob so they would not be recognized by their victims.

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Two of the shooters were dressed as uniformed police officers, while the others wore suits, ties, overcoats and hats, according to witnesses who saw the "police" leading the other men at gunpoint out of the garage after the shooting. John May's German Shepherd, Highball, who was leashed to a truck, began howling and barking, attracting the attention of two women who operated boarding houses across the street. One of them, Mrs. Landesman, sensed that something was dreadfully wrong and sent one of her roomers to the garage to see what was upsetting the dog. The man ran out, sickened at the sight. Frank Gusenberg was still alive after the killers left the scene and was rushed to the hospital shortly after police arrived at the scene. When the doctors had Gusenberg stabilized, police tried to question him but when asked who shot him, he replied "Nobody shot me", despite having sustained fourteen bullet wounds. It is believed that the St. Valentine's Day Massacre resulted from a plan devised by members of the Capone gang to eliminate George 'Bugs' Moran due to the rivalry between the two gangs.