St. Valentine’s Day Massacre | Fake Cops, Highball the Dog, Raccoon Bootlegger

This Valentine’s Day, Barely Historical is skipping the roses and going straight to the gunfire.

In this episode, Jo and Amanda dive into one of the most infamous crimes in American history: the St. Valentine’s Day Massacre of 1929, when Chicago’s Prohibition-era gang wars turned a holiday into a headline soaked in blood.

While the rest of the world was exchanging chocolates, Al Capone’s criminal empire and the North Side Gang led by Bugs Moran were exchanging bullets inside a garage on North Clark Street. Fake police uniforms, Tommy guns, a near-miss target, and a dog who absolutely did not consent to being part of mob history… it’s got everything.

We break down the chaos of 1920s Chicago organized crime, the brutal execution that shocked the nation, and the forensic science breakthrough that still couldn’t bring the case to court. Because nothing says romance like an unsolved massacre with holiday branding.

If you’re here for dark history, terrible men, worst decisions, and Prohibition-era violence that feels way too theatrical, you’re in the right place.

Plus: a game of Mobster or Mildly Unwell, raccoon bootlegging headlines, and the Barely Historical guarantee that this is not a cozy Valentine’s episode.

Hosted by Amanda and JoLynne~60 minutes | Explicit | Released 02/11/2026

Let's ruin Valentine's Day!

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