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

Chicago Daily News Headline | Photo courtesy of
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.

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This Post Has 39 Comments

  1. I did not expect this article to be about Al Capone but reading it I was glad that it was being because Al is so intriguing to learn about. The way the massacre was executed by McGurn’s men dressing as policemen is crazy and the fact that they succeeded really shows how far they would go to be the top gang. The detail provided in this article makes me want to learn more about this event so I am glad there is a second part.

  2. Auroara-Juhl Nikkels

    There are those questions that ask “if you could have a dinner table of anyone is history or fiction, who would you have?” and one of my answers is always Al Capone. His criminal empire, because an empire, was astounding. The sway he held over the city was astounding. Your article did a good job describing McGurn’s role in the massacre and how brilliant the plan was a whole, with the police car and “arresting” the criminals.

  3. Al Capone is one of the most notorious gangsters in American history, and this was a very well explained article of one of Al Capone’s men in action, conducting the Valentine’s Day Massacre. It was crazy that these two gangs were out for each other. It obviously took a line time to perfectly execute this plan. The author again did an amazing job chronologically listing out these series of events.

  4. Joshua Breard

    Al Capone is a criminal mastermind. It is crazy to see how he orchestrated this massacre with many moving pieces. The setting started off general but then got more specific as it went on. I think that little details like having some of McGurn’s men dressing up as cops is really smart and probably is more of nod to the work of Capone. Great job! Very interesting article!

  5. The article had a very great opening and is one of the things that got me most interested in wanting to finish reading it. It also had be in suspense the entire time and made me wonder more about what would happen next. I think the way they planned everything so well is crazy. Most times you don’t think of a gang actually doing that, at least i didn’t. I would have thought they just go forward with the plan but never really put in any thought into how much time it took them to plan it out.

  6. Mariet Loredo

    This was a great article, it really kept me engaged the whole time I was reading it. Learning about biggest gangs has always been very interesting to me. I find it crazy how a group of people came together to become the best and they would do anything to do that, even if it involved doing something like murder, such as the McGurn gang killing some of the Capone’s gang members. I have to give to the McGurn gang because it was a good idea for some of the men to dress up as cops to help them cover up what had just happened.

  7. This is such a crazy story. When I first read the title I thought the article was going to be about somebody killing people on valentines day for some reason but I was surprised to read this. The opening part of this article was almost like reading a movie it was great description and helped me get hooked into finishing the article. I think it is pretty interesting how they were able to pull off the police officer costume and fool not only their targets but bystanders when it was time to leave the crime scene. The intelligence of some people always amazes me and I wonder how some famous criminals would have impacted the world if they used their intelligence for the good.

  8. Thank you for this article! I didn’t know the story at all before reading this, and it blew my mind. It’s crazy how these gangs work and elaborate such plans to kill the others. I have to admit that this terrible event was well orchestrated and pretty smart. The fact that the witnesses thought that they were real policemen is just amazing, and to me, this plan was a perfect crime.

  9. I loved this article, it is very interesting! I have always been interested in learning about the mafias and the mob gangs, but I have never heard of this massacre. It is honestly very crazy how all of this happened within a matter of two minutes. In my opinion I believe that two minutes isn’t enough time to react to something to vivid and frightening. It is also pretty cool how the gang dressed up as police officers because that was just an upper hand on the other gang. Overall great article!

  10. It was really interesting to learn about Jack McGurn and his role in Al Capone’s gang. His survival of Moran’s attack and retaliation of that attack was a great story to read about. The article was written in a way where it feels as if we were with McGurn’s team in that garage as the event unfolded. I thought it was extremely intelligent of them to dress up as the police and take their long awaited revenge. I can’t wait to read part two and see what else is in store for them!

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