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September 23, 2016

To The One I Loathe: Chicago’s 1929 St.Valentine’s Day Massacre, Part I

Jack "Machine Gun" McGurn outside a phone booth in Chicago | Photo courtesy of Tumblr
Jack “Machine Gun” McGurn outside a phone booth in Chicago | Photo courtesy of Tumblr

Winner of the Fall 2016 StMU History Media Award for

Best Descriptive Article

Orders were given and on a cold morning on February 14, 1929, five men sped down the streets of Chicago in a stolen police car to ambush a rival gang in the hopes of ending their rule and territory in Chicago. The hit was believed to be ordered by Chicago’s most notorious gangster, Al Capone.1 Capone had been running most of the Chicago crime scene by this time but rival gangs did step into his territory from time to time and one that continued to be a nuisance was the gang belonging to George “Bugs” Moran. Moran was despised in Chicago and it was believed that Capone thought that if he allowed his men to put an end to Moran, he would be doing his city a great service.2

It is believed that one of Al Capone’s closest men, Jack McGurn, known as “Machine Gun” McGurn to his fellow members, was the man who put the idea into Capone’s head to take out Moran and his gang. McGurn was a man who enjoyed displaying his riches and made his wealth well known to all those around him. Once Moran took notice of McGurn, he set the assassination of McGurn into play and ordered two of his best hit men, Pete and Frank Gusenberg, to take out McGurn. The Gusenberg brothers left McGurn for dead and thought they had succeeded in killing him, but unbeknownst to them, McGurn survived the brutal attack.3 It was at this time that McGurn knew he would have to retaliate and he would not just take down the Gusenberg brothers, but the entire Moran gang.

After getting approval from Capone, the hit was strategically planned and carried out by McGurn. McGurn spent weeks following Moran and his men, watching every move they made to plan out his attack.4 McGurn would need a clever plan to get a man like Moran alone long enough to kill him. After tailing the Moran gang for some time, he learned that they frequented a small, dimly lit garage on North Clark Street. It was here that Moran accepted deliveries and distributed the alcohol he purchased for his bootlegging business.5 It was also the perfect spot to carry out McGurn’s gruesome plan.

George "Bugs" Moran | Photo courtesy of
George “Bugs” Moran | Photo courtesy of

McGurn knew what he needed to do to get the job finished. He placed a call that would allow him to get Moran and his men alone in the garage so that McGurn’s team would be able get in and out without being noticed. On February 13th Moran received word that a boat carrying a shipment of high quality whiskey had been raided on its way from Canada to Detroit, and the men who had taken the cargo were looking to unload it at a very reasonable price. Moran jumped at the offer and agreed to meet the men in his garage the following morning at 10:30AM. 6 Up to this point, Jack McGurn’s plan was going just as he had hoped. He rallied his men and had them ready to take down the man he had had his eye on ever since his attempted assassination on McGurn, George “Bugs” Moran.

2122 North Clark Street S.M.C. Cartage Co. George "Bugs" Moran's operations headquarters | Photo courtesy of
2122 North Clark Street
S.M.C. Cartage Co.
George “Bugs” Moran’s operations headquarters | Photo courtesy of

The next morning seven of Moran’s men, who included, Pete and Frank Gusenberg, John May, Albert R. Weinshank, James Clark, Adam Heyer, and Dr.Reinhart H. Schwimmer entered the garage at 2122 North Clark Street.7 Two men serving as lookouts for McGurn quickly alerted him that the men had entered the garage and McGurn and his men sprang into action. McGurn’s team consisted of, Fred Burke, John Scalise, James Ray and Joseph Lolodro and McGurn himself.8 Three of the men disguised themselves as police officers and all five piled into a stolen police car, sped down the icy streets of Chicago and into the small garage. They exited the car and demanded the seven men put their hands up and line up against the wall. Moran’s men thought they had been caught in a Prohibition raid and cooperated with the “police officers.” Despite being known as the gangland murder capital, what happened next would shock the city of Chicago.9 Carrying two Tommy guns and two twelve gauge shotguns, McGurn’s men opened fire on their victims, spraying them with bullets, the entire job lasting only two minutes.10 The men fell to the ground, their blood covering the floor of the garage in a thick layer. When the job was complete, the men walked out of the garage in such a manner as to make onlookers believe they were being arrested. The “police officers” escorted the “criminals” to the car, locked them in, then entered the car themselves and drove off.11


Continue reading Part II

  1. Laurence Bergreen, Capone The Man and The Era, (New York: Simon and Schuster, 1994), 305-306.
  2. Bergreen, Capone The Man and The Era, 306.
  3. Bergreen, Capone The Man and The Era, 305.
  4. Bergreen, Capone The Man and The Era, 306.
  5. Bergreen, Capone The Man and The Era, 307.
  6. Fred D. Pasley, Al Capone The Biography of a Self-Made Man (New York: Books for Libraries Press, 1930), 252.
  7. Jonathan Eig, Get Capone The Secret Plot That Captured America’s Most Wanted Gangster (New York: Simon and Schuster, 2010), 188.
  8. Pasley, Capone The Man and The Era, 259-260.
  9. Eig, Get Capone The Secret Plot That Captured America’s Most Wanted Gangster, 193.
  10. Eig, Get Capone The Secret Plot That Captured America’s Most Wanted Gangster, 189.
  11. Pasley, Al Capone The Biography of a Self-Made Man, 256.

Celina Resendez

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Recent Comments


  • Carlos Hinojosa

    It’s very interesting to learn what happened that day since it actually was a genius plan but what confuses me the most was the fact no one questioned all the shooting. I also heard a story that one of the victims was still alive when the real police arrived on the scene and when they asked what happened. He refused to talk to them and even was quoted to saying that no one killed him before he died. I personally don’t know why didn’t say anything, but I thought it was interesting. A very good article hope to read more.

  • Arsema Abera

    Last I checked valentine’s day was a day to celebrate love but instead was spent by a massacre in 1929 that something. I love reading books related to crime the plots, the adrenaline, the twists it all in there and this article did a great job at delivering those things that I expect in books. Though I have never heard of Al Capone it was fascinating to read about it.

  • Alondra Lozano

    I had never known about the St. Valentines massacre. This was a really interesting article! It is so crazy as to how McGurn waited for a while to find the perfect place, time, and plan to get rid of Moran and his gang. It’s so interesting to know that Al Capones closest member came up with the idea and successfully got away with it for that long.

  • Nelly Perez

    Al Capone is one of the world’s most known criminal in the U.S. The fact that his right hand man, Machine Gun, devised a plan to eliminate a rival gang and being cautious at not being caught is something. He laid low and fought back. I don’t get why they would steal a police car as a transport vehicle to the location and an escape car, but he probably thought it was a way to be discreet.

  • Jacob Silva

    Without a doubt Al Capone is one of the most notorious mob leaders in history. He committed so many crimes that there’s too many to keep track of or even think of Al Capone when you hear of some act of crime. I had never known there was a St Valentines day massacre, but hearing it was Capone that orchestrated it, it’s like no wonder when some people here the word gangster they associate it with Al Capone.

  • Jose Chaman

    This article has been very well written and has followed a clean timeline. It is very interesting to know how those times were in Chicago, since I am not a US citizen. Al Capone is undoubtedly a legend of the gangsters, and their way of operating was quite interesting and incredible in certain cases. The St. Valentine’s Massacre will undoubtedly be one of the most remembered made by Al Capone and his gang of criminals.

  • Bianca-Rhae Jacquez

    The St. Valentine’s day massacre is a important event in the mobs history. Al Capone is one the most well known mob leaders in history. The article does a great job of describing the details that happened during this event. I especially loved how the article wasn’t filled with unnecessary information it allows readers to understand the importance of this event easily.

  • Mariah Cavanaugh

    Great article! The St. Valentine’s day massacre is an infamous event in mob history, but I had no idea they pulled it off so seamlessly. I am amazed by the fact that they were able to steal a police car and carry out such a massacre in two minutes. There is not a single gang today that would be able to pull off such a feat!

  • Esperanza Rojas

    Al Capone’s name and his reputation, along with the St.Valentine’s Day Massacre, was something that everyone heard about. I personally always wanted to know the details of the massacre and why it made its mark in American history, and this article does a great job of that. I gives all the details but doesn’t overflow it with unnecessary information. This plan was a well thought out plan, assuming that Moran and his gang must have very high security but still find out his whereabouts for weeks and not get caught is impressive.

  • Raymond Munoz

    I have had a lot of previous knowledge about Chicago and Al Capone, so this article does a great job of reinforcing what I already know. With my previous knowledge of Chicago history I can already where the article will go in part two, but this will not keep me from reading it. I have found that the two part articles have a great way with details and I enjoy reading how they unfold a story.

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