This Week in History: The Valentine’s Day Massacre

Written by BlackbirdGo February 13, 2019
The History

On the Northside of Chicago, there is an empty lot that is turning to mud as the snow from a storm last week melts into the ground. There is an apartment complex nearby and a solitary tree that grows from the center of this piece of land. It’s just like any other unoccupied, unused, unassuming space in any city. What sets this lot apart from, well, most lots is that on February 14th, 1929, nearly a century ago, it was the site of a brutal slaying that shook Chicago.

The Roaring 20s were the height of prohibition and, thus, a time rife with criminal activity focused on giving the people what they wanted: booze. In Chicago, there were two rival gangs that had control over this trade: the Northside Irish gang headed by George “Bugs” Moran and the Southside Italian mob led by the notorious Al Capone. The two men had a lot in common. They were both in the business of bootlegging, both ran successful speakeasys, and both hated each other’s guts. This mutual hatred culminated in a bloodbath in a parking garage on the Northside on Valentine’s Day.

Inside this parking garage was the promise of access to cheap cases of Canadian whiskey. This is what is rumored to have led Bugs’ men to gather there on that day. Seven men belonging to the North Side Gang entered that concrete and brick complex—Johnny May, Bugs’ auto mechanic and his dog Highball, Frank and Pete Gusenberg, Bugs’ brother-in-law Jimmy Clark, Adam Heyer, Al Weinshank, and a quirky optometrist named Reinhardt Schwimmer, who tagged along for the ride because he liked the thrill of brushing elbows with gangsters. Bugs Moran was absent that day. He had gotten a late start that morning and, upon driving up to the garage a few minutes after the 10:30 a.m. rendezvous time, saw a police car sitting outside and drove past the garage, brushing off the police car’s presence as a mere shakedown. What Bugs didn’t know was that the police’s presence actually signified something much more sinister.

What occurred inside the building in Bugs’ absence wasn’t a police sting. As the men entered the building and were settling in to discuss the specifics of smuggling in this whiskey, several men dressed as police officers stormed the building. They ordered Bugs’ men to stand up with their faces to one of the brick walls in the garage. It was then that these interlopers—armed with Thompson submachine guns, AKA Tommy Guns—opened fire on Bugs’ men, unleashing 70 rounds into them before quickly making their exit. They left six dead men in their wake, a seventh struggling to stay alive, and poor Highball tied to the bumper of Johnny May’s truck, barking his head off.

It was the barking that piqued the interest of an older woman who lived nearby the site of this horror show, and it is what prompted her to send someone to see what was going on. This led to the discovery of the massacre and the involvement of actual police. Police found Frank Gusenberg barely alive and rushed him to the hospital. They asked him who was responsible for the treacherous act to which Gusenberg replied, “No one, no one shot me.” Gusenberg died within a few hours of being shot. It was immediately assumed that Al Capone was behind this carnage; however, he just so happened to be safely within his Florida home at the time of the killings and, therefore, could not have pulled the trigger. Thus, there was no way to pin this crime on Capone, and, consequently, no one was ever convicted for it.
There were three things that happened in the aftermath of this grisly murder. The first was the dissolution of the North Side Gang. Although Bugs had not been touched in this crime, most of the men who had died that day were his most trusted associates, meaning that his organization was now wildly disrupted and, thus, unsustainable. This seemed like a promising opportunity for Al Capone and his gang to capitalize on the turf now left behind by Bugs, but that was proving to be much easier said than done. Despite the fact that Al Capone was able to escape conviction, he was widely believed to be the cause of this shooting, which was just not a good look for him. Capone was respected in the community, perceived as a Robin Hood-esque figure who was bringing the people the spirits that they deserved. However, the violent nature of this crime had turned this positive public perception of the crime boss upside down. This is how Capone became Public Enemy #1.

The violence of this crime was also something that shed light on the underlying cause of organized crime in Chicago as well as the rest of America: prohibition. The public desire to end prohibition was now higher than ever, and with a city government that would often turn a blind eye to the shenanigans of gangsters, it was public pressure from Chicago citizens that eventually lead to the involvement of President Hoover and resultant arrest of violent criminal Al Capone for, of all things, tax evasion.

While Capone was jailed, the rest of the world continued to progress. Chicago elected a new mayor, a reform candidate named Anton Cermak, and the rest of the country elected a new President, Franklin D. Roosevelt. While Mayor Cermak remained chummy with certain gangsters, it was becoming apparent that Chicago was gaining an unsavory reputation as a lawless and violent city, a reputation that would not be economically fortuitous moving forward and therefore had to be rectified. As Chicago was making moves to minimize and end organized crime, Roosevelt was not only bringing an end to prohibition, he was also beginning to establish gun laws.

The gangsters who carried out this crime were armed with Tommy Guns, guns that were created too late to be used during World War I and had yet to be regulated to the extent that the common handgun was. The ease of acquisition and the efficiency of Tommy Guns made them the obvious choice for most gangsters and an excellent tool that advanced the crime wave in Chicago. The St. Valentine's Day Massacre was the first highly publicized murder that took place with the use of a Tommy Gun, shocking the public and catalyzing the need for regulation, resulting in FDR issuing the National Firearms Act of 1934 (a response that seems like an altruistic alternate reality when compared with gun control and mass shooting discourse in today’s day and age).

Disclaimer: Keep out of reach of children. For use only by adults 21 years of age and older.