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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.

Tags from the story

Al Capone

Saint Valentine’s Day Massacre

Recent Comments

Mariana Sandoval

The flow of the article was really well put together. I liked how it started with broad setting- Al Capone’s gang, then narrowed on one specific member and his plot to kill Maron, then leading to the aftermath and how he was able to get away with murder. I also found it interesting how well the plan went. It was a pretty genius idea to have some of McGurn’s men dress up as cops. Your sources were nice, and I like how you included primary sources for your images. It would be interesting to see what other primary sources are available.



8:46 am

Kassandra Guillen

I loved the opening of this article,for it really got my attention. This article is very well written as the events and plan of taking out Moran are very clear and precise. I look forward to reading part II of this article!



8:46 am

Vanessa Carrillo

This was such an interesting read and kept me captivated. I didn’t know much about this event that had occurred but to read what was actually going down during that time. This was a well structured article and good way to start this.



8:46 am

Jeanette Wimberly

Great opening! The beginning of your article was strongly written that I couldn’t help but stay engaged! Although I’ve heard of this massacre, I never knew this much strategy took place. Very well written!



8:46 am

Jezel Luna

Great introduction, it really grabbed my attention straight off the back. I really enjoyed the way you described every detail up until they assassination. I thought it was interesting how McGurn’s men disguised themselves as police officers, brilliant idea! You managed to keep me on my toes throughout the entire article. Excellent job!



8:46 am

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