The Bloody Story Of The St Valentine’s Day Massacre

The day America witnessed the fall of one of Chicago's most notorious gangsters and the rise of another.

A police reenactment of the St Valentine's Day Massacre.

February 14, 1929. A day that would live in infamy as one of the bloodiest in mob history.

7 Men. Gunned down in Chicago. The rise of a criminal empire and the fall of another: The St Valentine’s Day Massacre.

Chicago was the battleground as Al “Scarface” Capone (right, below) looked to consolidate his control of the city’s illegal trades: bootlegging, gambling and prostitution. In his way stood Irish American gangster George “Bugs” Moran and the North Side Gang.

A petty thief in his teens, Bugs went to prison three times before he even was 21. Following the introduction of Prohibition, Moran (left, below) operated a bootlegging operation out of a garage in Chicago.

Bugs Moran and Al Capone.

The Attack

On snowy Thursday, February 14th, 1929, a black unmarked police Cadillac pulled up to Moran’s headquarters – The SMC Cartage Company on 2122 North Clark Street.

Four men got out – two dressed as policemen and two in regular clothing. Believing it to be a raid, Bugs’ gang were lined up against the wall of the garage. The quartet then opened fire, firing off some 70 rounds of ammunition in the process via two Thompson submachine guns and a pair of shotguns – all of which were later linked back to Capone.

The Victims

Seven members of Moran’s gang were killed: Frank and Peter Gusenberg, James Clark, Aday Heyer, Reinhardt Schwimmer, Al Weinshank, and John May. The Gusenberg brothers were hired killers, Weinshank was a club owner and Clark a hit man, while Heyer did the books, and May was a mechanic.

The group were aged between 35 and 42 – considered middle aged for gangsters. May survived the initial shooting thanks to a Saint medal which was struck by a bullet. Unfortunately, the killers found himstill breathing and finished the job with a shotgun at point blank range.

They didn’t quite finish off Gusenberg, who lived on for three hours after the initial attack. Repeatedly asked by police in his final hours to identify who shot him, Gusenberg’s response remained the same: “Nobody shot me.”

It’s widely believed that the arrival of Weinshank at the garage sparked off the attack – he was the spitting image of Moran, the main target, and even dressed similarly to his mob boss employer. His arrival set the massacre in motion and possibly spared Moran the same fate.

Al Capone was never arrested – he told police he he was staying on Palm Island in Florida at the time. One of his right-hand men, Jack “Machine Gun” McGurn was thought to be the mastermind behind the plan, but he also beat the rap.

McGyrb was questioned by police but never arrested – his girlfriend earned herself the nickname “The blonde alibi” after she claimed they were together that afternoon.

Though Moran survived, the North Side Gang’s power began to wane. Moran got some modicum revenge though: in 1936 McGurn (below) was killed with Moran among the prime suspects.

What Happened Next

The Irish American crime boss would eventually leave Chicago and the gang life behind, returning to a life of robberies and petty crime. In July 1946 he was arrested on robbery charges and sentenced to 20 years in prison.

While behind bars, Moran got word that his old rival, Capone had died of a cardiac arrest after suffering a stroke. By then Capone had spent several decades behind bars, while his mental capabilities had deteriorated as a result of contracting syphilis earlier in his crime boss reign.

Released in 1957, Moran didn’t have long to enjoy his freedom – he was arrested again almost immediately on more robbery charges. The last survivor of the St Valentine’s Day Massacre eventually died of lung cancer in prison just a few months into a 10-year prison sentence.

To this day, no charges have ever been brought against anyone involved in the St Valentine’s Day massacre.

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Loaded staff writer Jack Beresford has produced content for Lad Bible, Axonn Media and a variety of online sports and news media outlets.