The Valentine’s Massacre

Happy Valentine’s Day Beyond the Threshold friends!

I hope everyone enjoyed the day with their loved ones and had a joyful time. Today, we will be exploring the darker side of Valentine’s Day, grab some snacks, and get ready to learn some very interesting Valentine’s Day history.

 (TW: Murder, graphic images, death, gang violence)

On February 14th in 1929, a devastating massacre erupted in Chicago's north end. This massacre resulted in 7 tragic deaths. 

In 1929, in Chicago, 7 men were murdered in a mass shooting. What led up to an attack of this degree? Gang violence. A common occurrence, especially in 1920’s Chicago, gang violence was at the beginning of this day, ending in tragedy. Al Capone was Chicago’s leading man when it came to the food chain of Gangs. Capone wanted to be top of the food chain, eliminating his rivals from the market of distributing, gambling, and prostitution. According to History, “...seven men associated with the Irish gangster George ‘Bugs’ Moran, one of Capone’s longtime enemies, were shot to death by several men dressed as policemen.” This case remains unsolved, with heavy speculation that Al Capone was the force behind the massacre, but no confirmed connection has been established. 

Let’s take it back and learn some of the history surrounding valentines’ days creation. The gang violence that occurred on February 14th, resulting in multiple deaths, was not the first murder/death to occur on our beloved holiday, Valentine’s. Oddly enough, another death occurred in a different century: “St. Valentine’s Day was originally a Catholic feast day established in A.D. 496 to honor a third-century priest named Valentine who was executed on February 14.” This isn’t the real reason we celebrate Valentine’s Day as we know it now. In mid 17th century England, Valentine’s Day was a folk practice dedicated to celebrating the springtime. This does not relate to the death of St. valentine even though many people believe them to be connected. 

In fact, this developed from a folk practice into “a custom whereby men and women were paired together as Valentines through random drawings; the matchmaking lottery became a good omen for a couple’s future marriage.” In which love notes and ‘valentines’ cards were later developed. Although after giving you all that information, that’s the most credible development of the holiday, but still not fully confirmed to be the true reason! Another theory derives from” the ancient Roman festival of Lupercalia, known for its feasts, ritual sacrifice, and sexually charged celebrations on February 15.” INSANE. Did you know all this lore about valentines cause I sure didn’t!

So anyway, back to the original story, we have 7 murders and no idea why.  George Moran ran his operations out of a garage at 2122 North Clark Street. On February 14, seven members of his operation were gunned down while standing in line up, facing the wall of the garage. It is said that nearly 70 rounds of ammunition were fired. One gang member, Frank Gusenberg, was found barely alive, and in the few minutes before he died, the cops pressed him hard to make him talk about what had happened, but Gusenberg wouldn’t give any information. 

This massacre marked an end to any gang opposition to Al Capone’s rule. Al Capone was then heavily investigated until he was arrested for completely unrelated crimes, in which he served 9 months in jail before being released for good behavior. Capone was indicted for evasion of federal income tax. Capone was sentenced to 11 years in prison, first in Atlanta and later at Alcatraz. He was released in 1939 and died at his Florida home in 1947.

I hope you enjoyed reading this and learned some history about the holiday that seems to attract a lot of death. The St. Valentine’s Day massacre was so interesting to research, so I really hope you all learned something new and enjoyed it just as much as I did. 

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Goodbye for now, see you in the next one! 

Works cited 

A&E Television Networks. (2025, May 28). St. Valentine’s Day Massacre. History.com. https://www.history.com/articles/saint-valentines-day-massacre