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. 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.

  2. 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!

  3. 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.

  4. Raymond Nash Munoz III

    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.

  5. Emily Jensen

    This article is very well put together and doesn’t stray away from the storyline, which I appreciate. Prior to reading the article I hadn’t heard of Jack McGurn or his idea to have Al Capone ‘put an end to Moran.’ I have always found Al Capone and his comrades interesting and can never turn down a good article about them.

  6. Reading about Al Capone and the crimes he committed is very interesting. This article did a very good job at narrating a specific event of the years Al Capone was a gangster. I can’t wait to read about the next part of this article. It is also very fascinating to read about how crime was during the early nineteen hundreds.

  7. Christopher Hohman

    nice article. I find Al Capone and his bootlegging businesses very fascinating. It is hard to believe that Chicago, for much of its life time has been home to some of the worst gang violence in the United States. Al Capone’s iron grip must have filled many ordinary citizens with fear, but also lined some citizen’s pockets with money. The St. Valentine’s day massacre will go down as by far the most brutal act he ordered carried out. Thank God for Elliot Ness

  8. This article does a great job at keeping on topic and describing what had happened at this infamous event. This event stands out quite a bit in the gangster world during that time possibly because of its brutality and has become well known because of it. I liked that there was not a lot of focus on a particular person. The author touched on who was involved and a little bit of the personal vengeance that was felt needed to be had, but it focused on the event and how it come about all the way till the end when they exited the building fooling the public.

  9. This part of the article did a great job of telling the first part of the massacre. I was not that familiar with the event, but the article did a good job of laying down the foundation for what is going to happen next. The article does an excellent job of making the reader want more, making the article so much better.

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