In 1929, George "Bugs" Moran was the boss of the long-established North Side Gang, formerly headed by Dion O'Banion who was murdered by four gunmen five years earlier in his flower shop on North State Street. Everyone who had taken command of the North Siders since O'Banion's rule had been murdered, supposedly by various members or associates of the Capone organization. This massacre was allegedly planned by the Capone mob in retaliation for an unsuccessful attempt by Frank Gusenberg and his brother Peter to murder Jack McGurn earlier in the year and for the North Side Gang's complicity in the murders of Pasqualino "Patsy" Lolordo and Antonio "The Scourge" Lombardo – both had been presidents of the Unione Siciliana, the local Mafia, and close associates of Capone. Bugs Moran's muscling in on a Capone-run dog track in the Chicago suburbs, his takeover of several Capone-owned saloons that he insisted were in his territory, and the general rivalry between Moran and Capone for complete control of the lucrative Chicago bootlegging business were probable contributing factors to this incident.
The plan was to lure Bugs Moran to the SMC Cartage warehouse on North Clark Street. Contrary to common belief, this plan did not intend to eliminate the entire North Side gang – just Moran, and perhaps two or three of his lieutenants. It is usually assumed that they were lured to the garage with the promise of a stolen, cut-rate shipment of whiskey, supplied by Detroit's Purple Gang, also associates of Capone. However, some recent studies dispute this, although there seems to have been hardly any other good reason for so many of the North Siders to be there. One of these theories states that all of the victims (with the exception of John May) were dressed in their best clothes, which would not have been suitable for unloading a large shipment of whiskey crates and driving it away – even though this is how they, and other gangsters, were usually dressed at the time. The Gusenberg brothers were also supposed to drive two empty trucks to Detroit that day to pick up two loads of stolen Canadian whiskey.
On St. Valentine's Day, most of the Moran gang had already arrived at the warehouse by approximately 10:30 AM. Moran was not there, having left his Parkway Hotel apartment late. As Moran and one of his men, Ted Newberry, approached the rear of the warehouse from a side street they saw the police car pull up. They immediately turned and retraced their steps, going to a nearby coffee shop. On the way, they ran into another gang member, Henry Gusenberg, and warned him away from the place. A fourth gang member, Willie Marks, was also on his way to the garage when he spotted the police car. Ducking into a doorway, he jotted down the license number before leaving the neighborhood.
Capone's lookouts likely mistook one of Moran's men for Moran himself – probably Albert Weinshank, who was the same height and build. That morning the physical similarity between the two men was enhanced by their dress: both happened to be wearing the same color overcoats and hats. Witnesses outside the garage saw a Cadillac sedan pull to a stop in front of the garage. Four men, two dressed in police uniform, emerged and walked inside. The two fake police officers, carrying shotguns, entered the rear portion of the garage and found members of Moran's gang and two gang collaborators, Reinhart Schwimmer and John May, who was fixing one of the trucks. The "police officers" then ordered the men to line up against the wall.
The two "police officers" then signaled to the pair in civilian clothes who had accompanied them. Two of the killers opened fire with Thompson sub-machine guns, one containing a 20-round box magazine and the other a 50-round drum. They were thorough, spraying their victims left and right, even continuing to fire after all seven had hit the floor. The seven men were ripped apart in the volley, and two shotgun blasts afterward all but obliterated the faces of John May and James Clark, according to the coroner's report. To give the appearance that everything was under control, the men in street clothes came out with their hands up, prodded by the two uniformed police officers. Inside the garage, the only survivors in the warehouse were Highball (May's German Shepherd) and Frank Gusenberg. Despite fourteen bullet wounds, he was still conscious, but died three hours later, refusing to utter a word about the identities of the killers.
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