Normally Valentine’s Day is about love but on the cold north side of Chicago in 1929 it was revenge not romance that filled the newspapers. Four members of Al Capone’s Chicago Outfit most likely Fred Burke, James Ray, John Scalise, and Albert Anselmi lured seven members of Bugs Moran’s Northside gang into a garage to discuss buying a large amount of illegal whiskey. When Peter and Frank Gusenburg, Adam Heyer, Reinhart Schwimmer, Albert Weinshank , James May, and Bug’s second in command Albert Kachellek arrived they weren’t greeted by a ton of illegal hooch but by two men in suits and another two in police uniforms. In what they though was a police sting the men were disarmed and forced against the wall of the garage but the handcuffs never came out. Instead, all seven men were gunned down by two Thompson submachine guns a shotgun and one revolver.

After the slaying the four men left in a black car they made to look like a police car. By the time the police got to the scene they were gone and only Frank was still alive. In true gangster fashion he refused to tell the cops who was responsible for his friend’s and eventually his own deaths. Bugs Moran the leader of the gang was the original target of the hit, but he was running late that day and by the time he got to the place the police were already there. It’s said the shooters may have mistaken Weinschenk for Moran because they looked very similar. No one was ever charged but later investigations did find that Fred Burkes Tommy gun was one of the ones used in the shooting.

While this was the most violent gang related attack in Chicago’s history the city was use to the warring between the Irish mob of Chicago’s north side and the Italian mafia. Since alcohol was banned on October 28th 1919 what were once small times gangs used the new market for illegal booze to grow and with that came a massive increase in gang related violence. It’s supposed the Valentine’s Day Massacre was revenge for the murder of Patsy Lolordo and her Antonio Lombardo close friends and crime partners of Capone’s by the Moran Gang in an effort to weaken Capone. The effects of massacre where both a boost to Capone’s crime business but also lead to his eventual demise.

The shooting left the Moran gang weak, and so they could no longer check the power of Capone’s Chicago Outfit. In the end Capone owned Chicago and used his over the top violence to keep control. The public was disgusted by the massacre and the constant violence surrounding organized crime and pressure was placed from the press on law enforcement to get the mob out of America’s cities. With Capone being the face of organized crime in America he was made public enemy number one. Capone was soon on the top of the FBI’s and every major police forces watch list. He was arrested 3 times and sentenced to prison twice but some how Capone was able to skirt the time and never spent more than a week in jail. Until finally his luck ran out.

On October 17th 1931 Capone was sentenced to 11 years for tax evasion. Spending most of it in the famous Alcatraz. He would only serve around 8 years but this time it had nothing to do with mob owned justice and instead the fact that his mind was failing him. Capone had been diagnosed with serious syphilis while in prison and by the time he was paroled in November 16th 1939 he was anything but the criminal master mind he used to be. He would pass away 8 years later on January 25th 1947 from complications of pneumonia. While the deaths of the 7 men on that fateful Valentine’s Day had been short, Capone’s was a long-drawn-out decline.

Partly in response to the role illegal alcohol played in bankrolling the gangster lifestyle congress repealed prohibition with the 21st amendment on December 5th 1933? The era of speakeasy’s and Tommy guns was over. With Capone’s death organized crime in Chicago and the rest of the country still existed but it lost most of its glamour and its brazen display violence. It wasn’t until Joe Vallchi broke the code of silence in the 60s that Italian mob was once again in the headlines nationwide. While we might glamorize the flashy and exciting lives of guys like Capone and Moran it’s important to know that life for these guys was bloody and in end their era just like their lives was short.

Memorandum for John May: