At 10:30 on the morning of February 14, 1929, seven members of Chicago's North Side Gang were lined up against a wall inside one of their leader's bootlegging garages and gunned down in a barrage of bullets by men dressed in trench coats and police uniforms, leaving a scene of carnage that to this day is referred to as the bloodiest day in mob history – AKA the Valentine's Day Massacre.
Police determined that the men had been shot down by nearly 70 rounds of ammunition fired from Thompson sub-machine guns, and a few were finished off with close-range shotgun blasts. And, though one man was still alive when police arrived, he refused to reveal the truth of what had happened, taking with him to his grave the instigators of the ambush.
No one was ever convicted for these murders, and, though Al Capone was closely tied to and believed by police to have been involved in the murders, his alibi was solid, and he and the rest of his South Side Gang were able to get away clean.
On the morning of February 14, 1929, five members of Chicago's notorious South Side Gang (accompanied by two associates) were coerced into meeting an unknown source at their bootlegging garage to apparently get their hands on a lucrative supply of stolen whiskey. At the time, Prohibition was still drying up the streets, making the black market the only place for people to land some pricey booze – and the mob was the cornerstone of the market.
Shortly after the South Side Gang members arrived, still waiting for their boss and owner of the garage Bugs Moran to make his way over from his Parkway Hotel apartment, they were suddenly interrupted by two police officers and two civilians who were apparently there to conduct a raid. However, the interrupters' true intent was quickly revealed as the men dressed in police uniforms ordered their prisoners to stand facing a far wall, at which point the men in civilian trench coats removed two Thompson sub-machine guns and proceeded to spray bullets into the backs of the men until each of them had fallen to ground, covering the wall in blood and bullet holes.
After all seven of the men had fallen, the killers walked among their bodies with shotguns in hand to make sure that they were all dead, finishing off two of the men, John May and James Clark, by firing a final round into each of their heads.
To avoid raising the suspicions of passerby, the men dressed as police made it appear as though they were completing a standard arrest, escorting the two men in overcoats from the building, effectively making their getaway.
By the time the real police arrived, the criminals were long gone, and the one victim that was left barely alive, Frank Gusenberg, refused to reveal the truth of the incident to police, repeatedly claiming, "Nobody shot me," despite the 14 bullet holes he bore.
Assuming that the rumors are true, Capone had it out for Moran, the leader of the North Side Gang and the top competitor to Capone's control over the Chicago bootlegging industry. After a number of run ins between the two gang leaders, Capone believed that Moran needed to be taken out, as he had begun threatening Capone's territory by taking control over certain southern suburbs.
It is believed that this massacre was, in fact, organized by Capone from his Florida home with the goal of eliminating Moran and sending a strong message to the rest of his Northsiders; however, things didn't quite go as planned – Moran wasn't even in the building when the massacre took place. Storylines deviate here, but it is said that Moran happened to leave late from his nearby apartment and narrowly missed the gunfire, while others say that he noticed the police car outside of his garage and fled the scene before he was detected. Regardless of how he escaped, Moran was able to lead police to Capone's trail, telling police that "only Capone kills like that." However, authorities were never able to connect the murders to Capone or his South Side Gang, and to this day the case remains unsolved.