February 14, 1929
It is a snowy morning, February 14, 1929. Seven men—most of them members of George “Bugs” Moran’s North Side Gang—gather inside a garage in Chicago’s Lincoln Park area, apparently awaiting the arrival of a truck of bootleg whisky. The location is a known hangout for the gang.
At approximately 10:30 a.m. a squad car pulls up in front of the garage. Two men wearing police uniforms and carrying guns step out. They enter the garage and demand Moran’s men drop their weapons and face the wall—this is a raid. The “policemen” then open a back door and let in more men, these ones dressed in suits, ties and hats and also carrying weapons.
Shortly after that the armed group opens fire on Moran’s gang. Both machine guns and rifles are used in the bloody attack, and over 70 rounds of ammunition are sprayed into Moran’s men and into the back wall.
The job done, some of the killers exit through the rear door of the garage. But the rest—the two “policemen” and two of the “civilians”—leave through the front entrance. The civilians are being forced out at gunpoint, their hands raised as if under arrest. To any onlookers it appears that the police have matters well in hand.
Alarmed by the commotion, Jeanette Landesman, ironing clothes in a nearby boarding house, sends over a lodger to investigate. The lodger returns a short while later, ashen-faced, and tells Jeanette to call the police—something terrible has happened.
When the real police arrive, they find a gruesome site. The St. Valentine’s Day Massacre, as it is later dubbed, is the bloodiest hit in Chicago mob history, and unquestionably the most infamous gang assassination of all time.
Six of the victims die outright, but one—Frank Gusenberg—is miraculously still alive and trying to drag himself to the door. When asked by police who did it, Gusenberg refuses to talk. He dies three hours later.
There are no survivors and no one is brought to trial, but the chain of events seems clear. This hit is just the latest in the long line of skirmishes that Bugs Moran’s North Side Gang and Al Capone’s South Side Gang have been engaged in for years. The costs have been high on both sides. On that morning in February, Capone makes a bid for supremacy with an attack on Moran. The only problem is that Moran isn’t there.
The investigation seems to drag on for years, with the police pursuing several leads, but strangely never following through. It is not until 1934 that a low-level hood—Byron Bolton—is able to fill in the details of what really happened on that St. Valentine’s Day.
According to Bolton, in October or November of 1928 Capone and some of his men sat down at a Wisconsin resort and planned the hit, intending to kill Moran and several of his gang. The strategy was for Bolton to keep a look-out near the garage and alert the hit team, waiting at the Circus Café, the moment that Moran appeared. That morning, when a group of Moran’s men arrived at the garage, Bolton mistook one of them for Moran. The target apparently spotted, Bolton gave the signal and the cars began to arrive.
But Moran was late in reaching the garage, and when he pulled up and saw a police car there he ducked into a coffee shop instead. Bumping into another of his men along the way, he told him to avoid the garage as it was being raided.
This mistake didn’t really matter, though—the hit did the trick and Moran’s operations were dealt a deadly blow. But it also brought a lot of unwanted attention to Capone, even though he was in Florida at the time and had an alibi. In 1930 Capone became Public Enemy Number One, and by the end of 1933 he was in jail serving an eleven-year stretch.
Dying in his bed in 1947, Capone had never again been able to regain the power he wielded during his Chicago heydays. And the famous Massacre wall, the one that the victims were facing when they were shot? It’s now part of the Mob Museum in Las Vegas, minus a few souvenir bricks—gruesome mementoes.