Jack McGurn featured prominently within the Capone syndicate. Of all of Capone's people, he was responsible for many of Chicago's gangland murders, often without Capone's consent. McGurn upset Capone on a number of occasions for going over the top in violence, because everything McGurn did reflected on Capone in the media. Capone liked things kept quiet, but McGurn's reckless behaviour of killing and maiming, prompted Capone to implore him not to take actions unless he had permission.
"Bugs" Moran had Capone on his list for assassination for years now, but realised the more reasonable goal of knocking off his main henchman Jack McGurn. He dispatched the brothers Frank and Peter Gusenberg for the job.
After days of watching and following McGurn, they opened fire while McGurn was using a public payphone inside a hotel lobby. Certain they had accomplished the mission, the brothers fled. But McGurn was lucky. After the initial salvo, he collapsed below the glass and was afforded some shielding from the bullets by the wood in the booth. Nevertheless, he was severely shot and was close to death. Because of the location of the shooting, McGurn was afforded quick access to medical attention. The worst scenario for the Moran gang had occurred, the survival of the most violent man in Capone's service.
Capone did not like the situation. The heat on his organisation was bad enough as it was, but knew that such an action was likely to set the gang wars on a new and deadly course. It is a common misconception that Capone masterminded the St. Valentine's Day Massacre. While it is true it was to his interest that these people were eliminated, he would have preferred it not occur. After all, this was McGurn's vendetta against Moran. So Capone left Chicago for Miami, to be as far away from complicity as possible.
McGurn planned carefully for this hit. He utilised two seasoned gunmen from Capone's group, Albert Anselmi and John Scalise. Also employed was a Chicago outsider, Fred Burke, and it is assumed that the fourth was another outsider, possibly a recruit from a gang in alliance with Capone's.
The plan was simple. Pose as police and pretend a raid. The question was, to raid what? The idea was to lure the gang together by creating a liquor transaction of Canadian Whisky from a 'supposed' dealer. This dealer would inform McGurn of the pickup location and the plan would execute. To ensure the snare would come off properly, it was tested to ensure the Moran boys were comfortable with the arrangement. After the first shipment, the trust factor ensured that Moran gang's guard would be down.
On the next occasion, Moran set the place of transaction to be at the S.M.C. Company garage. Moran would be handling the cash himself. McGurn was informed that Moran would be there himself at 10:30 am on February 14, a Thursday. There was one problem. The men McGurn hired for lookouts, didn't exactly know what Moran looked like
Valentine's Day 1929, Chicago. Valentine's Day occurs at an odd time of the year considering the aspect of the celebration. The day we see lots of heart-shaped cards, banners, and candy. A celebration of our mates, or the day we attempt to win the heart of one.
In Chicago, it was breezy, and very chilly at -8°C. The people were in place. The lookouts watched over the area, the men masquerading as police were ready to go. The lookouts reported they saw "Bugs" Moran enter the garage. The plan went into action. A police car drives up to the garage and witnesses alerted to the siren hurry to their windows. They see four men get out. Two policemen and two in plain clothes. They enter the garage and walk quickly through a corridor and announce that everyone is under arrest. With their lives only moments from ending, the seven men are confused and non-resistant to the 'police'. Present are Frank and Peter Gusenberg, Adam Heyer, James Clark, John May, A.R. Weinshank, and Dr. R. Schwimmer. Dr. Schwimmer, is the only innocent of the seven men. It is still a matter of historical debate as to Schwimmer's reasons for being at the garage that day. It is generally assumed he was a friend or relative of one the Moran gang. Whatever the reasons for his appearance, it could not have been on a worse occasion. Instead, it was Moran's lucky delay that spared him his life.
After the noise of shouting and ordering the men against the wall, there was a brief silence. A silence like a hollow, and echoing clicks. With the terrified men realising, now, it will soon be very loud, but for a moment for only them. The massacre began. With a loud crack the shotguns burst, the Tommy guns spat with ear-splitting ceaseless cracks of their own. It seemed an eternity of noise. Then a brief quiet. The gunmen now approached their victims and stood above them to make sure they would not live. They shot them where they lay, negotiating the shots by the living reflexes still present within their bodies.
The men then left. As curious onlookers watched, they saw two policemen, apparently 'arresting' two other men. They then got into the police car and drove away. McGurn, careful to keep his whereabouts above suspicion, was delighted at the result. But the job was not a complete success, "Bugs" Moran had lived.
When the real police arrived, they discovered a carnage not seen since the beginnings of the Jazz Age. Witnesses appeared confused. They couldn't distinguish at what point the police arrived and departed. In fact, they ended up not seeing anyone except the police. The seeds of confusions and conflicting accounts was to lead to a very difficult investigation.
The murders instantly brought national and even world attention. It was an outrage for the members of enforcement officers. Who take it quite personal when a criminal will disguise themselves as police officer. It was believed early on that the police shot the men at the garage. This was simply not the case. Although it was perhaps not intended, the police ended up looking as though they were being framed.
McGurn had what he wanted, a clean annihilation of the chance of an open and shut case. Capone was immediately suspected of involvement, but was safely away on holiday in Florida during the time of the murders. McGurn himself acquired an alibi of being nowhere near the scene, spending all day with his girlfriend.
While the massacre was unsuccessful for the intention of assassinating Moran, the Moran gang never did recover from the incident to capacity it had. It stopped the growth of Moran's interests. In the end, he eventually lived out the rest of his days in prison.
Ultimately, not one person was convicted for the murders on St. Valentines Day. However, fate played its justice on the main players of the massacre. McGurn was shot by gunmen in bowling alley on the eve of St. Valentines Day 1936 (it was a Thursday). Anselmi and Scalise ultimately died at the hands of Al Capone, in the infamous 'baseball bat' incident as dramatised in "The Untouchables" with Robert De Niro as Capone.
Al Capone was a wonder of the age. It should be pointed out that Capone was the 'generous' gangster. He actually helped build Cicero and Chicago projects, gave to the needy, helped the elderly, and was great with kids. While he may have consciously did this for improving his image, he did try to be an active member of the community. He liked sports, baseball, boxing, and horse racing. He gave away a lot of his ill-gotten gains, and it was part of the defence for his tax evasion trial. But Capone ultimately went to prison for tax evasion, and died in 1947 from complications arising from syphilis.
The St. Valentine's Day Massacre is but one of several murders in those days of the Jazz Age. It was typical in that few members of gangland murders were ever brought to justice. Chicago and Cicero grew from these hard times, and have bequeathed to us a story.