Least Lovely Valentine’s Day in History

Rebecca Jolius, Editor

Today in History:

Valentine’s Day is typically a holiday that people around the world celebrate love and friendships of all kinds. Typically it’s happy. But 90 years ago today, the least loving Valentine’s Day took place. In 1929, on February 14th, seven typical gangsters were killed execution style in the midst of a brooding gang rivalry Chicago. In what is known as the St.Valentine’s Massacre, it is believed that notorious gangster Al Capone called for a hit against rival gang leader George “Bugs” Moran. But why?  A bloody massacre on the day of love.


Al Capone, leader of the South Side gang and Chicago Outfit, had come to tense cross words with Bugs Moran, leader of the North Side gang. As the bootlegging business of the prohibition days were so profitable, neither gang could afford to lose to another. Each gang would do something to cause the other to retaliate. However, Bugs Moran had gone to extremes to upset Capone that offset the balance. He burned down and broke into Capone’s properties, and hits on his associates. Reasonably, Capone had enough of his adversary and ordered the final hit against him.

The Massacre

In the early morning hours, Chicago Outfit associates dressed as police officers and ordered North Side members into a garage. Seven men were ordered against a wall, and killed immediately with a Thompson submachine gun. All but one died immediately, Frank Gusenberg, who refused to give up the identities of his killers. None of these seven men killed were Bugs Moran, the prime target.

The Mastermind

Although Al Capone is largely suspected to have organized the massacre, he was never prosecuted for the crime. He was investigated, however the discussion turned into talks of his taxes, not his supposed murders. In addition, associates of Capone claimed to have witnessed him plan the massacre, but this path was not walked further. In the end, Capone is largely suspected, and mostly likely organized, the least lovely Valentine’s Day in history.