In 1929, Valentine’s Day Was Associated with Violence, Not Love & Romance

Chicago officials re-enact St. Valentine's Day massacre, the most atrocious in Chicago's history, which was planned in Al (Scarface) Capone's Florida residence
NY Daily News Archive via Getty Images

Generally, Valentine’s Day is all about love, romance, and chocolates. However, on February 14, 1929, the streets of Chicago soon became the scene for what would be called The St. Valentine’s Day Massacre. In the 1920s, during the age of Prohibition, the city of Chicago was known for violence and was the home of gangsters such as Al Capone. Capone became extremely wealthy after taking over as the head of illegal activities in town such as bootlegging, running speakeasies, gambling, and prostitution. While he earned over $60 million a year, it hit him with lots of enemies too.

On this particular day, seven men associated with the gangster George “Bugs” Moran, an enemy of Capone, were murdered by men dressed as policemen after 70 rounds of ammunition were fired. When the real policemen arrived, only one gang member was alive but wouldn’t talk about what happened before he succumbed to death too.

Portrait of gangster George 'Bugs' Moran (1891 - 1957), 1930

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The crime was never officially solved but many associate it with Capone, who had it out for Moran and his men. Moran just missed being murdered by a few minutes and when asked about the crimes, he said, “Only Capone kills like that.” When Capone was asked for his comment, he responded, “The only man who kills like that is Bugs Moran.” He claims to have been at home in Florida at the time but that certainly doesn’t mean he didn’t hire someone to carry out the murders. Even so, it was never brought to trial.

Infamous gangster Al Capone smokes a cigar on the train carrying him to the federal penitentiary in Atlanta where he will start serving an eleven-year sentence.

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Even though the St. Valentine’s Day Massacre made Capone the top dog in the world of illegal dealings, it certainly put a bigger mark on his head as newspapers called him “Public Enemy No. 1.” Federal authorities began investigating him more closely and he ended up being arrested and released for various crimes. Eventually, he was caught for income tax evasion and served at the infamous Alcatraz. Capone was released in 1939 and died in 1947.

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