The year is 1929. Herbert Hoover is assuming the office of the Presidency after assuring "a chicken in every pot"(in totally unrelated news, the stock market would crash by the end of October), the Cubs are gearing up for yet another one of their close-but-no-cigar trips to the postseason, and Al Capone is getting more and more fed up with Bugs Moran and his cronies in the North Side Gang stealing his business.
Prohibition had by this point been in full effect for 9 years, and there seemed to be new criminal enterprises related to alcohol popping up every day. And of course, if there was any business to be had, Capone demanded a piece of the action. So one can imagine that Capone wouldn't be too pleased with a pushy bunch of upstarts competing with him. The final straw was the murder of two of Capone's close associates at the hands of the Moran gang.
So on the morning of February 14, Capone initiated a plan for revenge. It was planned out that they were going to lure Bugs Moran to a warehouse on North Clark St. Various theories exist about what the lure was, but it is generally agreed that they fed the Moran gang information about a stolen shipment of whiskey, courtesy of the Detroit Mob. By 10:30 AM, most of Moran's gang had shown up to the garage, with the exception of Moran himself, who was running late. As Moran was walking with one of his men to the warehouse, they happened to see a police car. Being logical mobsters, they immediately turned tail and ran. On their way, they happened across another one of Moran's men, who they warned away from the warehouse. The others who were already waiting at the warehouse weren't so lucky. The police car that Moran saw on his way to the warehouse was a fake, as were the men wearing uniforms. Once the impostor cops saw the person that they thought was Moran enter the building, they immediately rolled into the building and told the seven mobsters in the garage to line up against the wall. At that very moment, two Tommy Gun-toting folks in civilian garb opened fire on the mobsters, painting the wall with bullets.
To effect their getaway, the phony cops(who were really hit men working for Capone) ushered the trigger men out of the garage so as to make it look like they were merely making an arrest. Two women who happened to be staying across the street heard the ruckus and alerted the authorities. When the police(the real ones this time) arrived on the scene, they saw the grisly aftermath. Five of the men were ripped apart by the hail of bullets, and the other two had their faces obliterated by shotgun blasts after the fact. The only two organisms left alive were a German Shepherd owned by one of the deceased mobsters, and Frank Gusenberg, who was somehow still clinging to life despite having been shot fourteen times. He maintained consciousness and life for another three hours, but in true gangland fashion the only thing he would say was that "nobody shot me."
This sense of mystique carried over into the investigation. Initially under the impression that this had to be the work of the Detroit Mob, authorities went after several members of the Purple Gang. However, the men were quickly cleared by the police. Then, a week after the massacre, a 1927 Cadillac was found on fire in a garage on Wood Street. This was found to be the car used by the mobsters to get away. Eventually a lead was found on the killer though. A truck driver later came forward to say that he'd fun into the phony cops the morning of the massacre. While trying to make it right, he got a description of one of the mobsters, who was discovered to be Fred Burke. Eventually Burke's home in Wisconsin was raided, and much of the materials found could be traced back to the massacre. Burke was sent to prison for other crimes and died there in 1940. To this day, nobody has ever been formally brought up on charges, and the Saint Valentine's Day Massacre has gone down in history as the most infamous killing in Chicago's gangland history.
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