The Valentines Day Massacre
REDRUM true crime
redrumpodcast
4.6 • 532 Ratings
🗓️ 12 February 2026
⏱️ 32 minutes
🧾️ Download transcript
Summary
2 police officers walked into an illegal bootlegging operation in Chicago and ordered the 7 men inside to stand facing the back wall. What happened next made it clear that the 2 men weren't police officers... and this was a mass execution.
Sign up for the free REDRUM newsletter, full of all things true crime, as well as a run down of all the latest REDRUM cases. This will only ever come to you once a month... I'm no fan of spam.
https://www.surveymonkey.com/r/SWYZGKL
Instagram: https://www.instagram.com/redrumtruecrime/
Facebook: https://www.facebook.com/redrumtruecrime/
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | It's Valentine's Day 1929. |
| 0:07.2 | Seven men stand shoulder to shoulder facing a brick wall inside a garage in Chicago. |
| 0:12.8 | They don't run, they don't resist, they believe they're being arrested. |
| 0:18.0 | Two men dressed as police officers have just ordered them into position, and this |
| 0:22.9 | isn't unusual. Raids are common in this day and age, and questioning is routine. For men |
| 0:28.8 | involved in their line of work, this is part of daily life. But while the men are stood facing |
| 0:34.6 | the wall, the sound behind them changes. |
| 0:38.3 | Instead of handcuffs, the clattering of sub-machine guns being raised can be heard. |
| 0:45.3 | This is Red Rum. Stories about the true victims of crime. |
| 0:49.3 | I upload episodes on Mondays and Thursdays and make sure you're subscribed so you never miss an episode. |
| 0:53.3 | Today's case is a Valentine special. It is the St Valentine's Massacre of 1929. |
| 1:02.4 | Our case begins in January 1920 and in America, the 18th Amendment had just made it illegal to make, |
| 1:09.8 | sell or transport alcohol. |
| 1:12.2 | In theory, the law was just that. |
| 1:15.2 | It's a legal thing and there's no way around it, but in practice, it was almost laughable. |
| 1:21.4 | People still want to drink at this point. |
| 1:24.3 | Parties still want champagne and whiskey and gin. Cities still crave that nightlife |
| 1:31.0 | and in Chicago, that want for alcohol for booze is met by the people who live there. Chicago in 1920s |
| 1:40.0 | was very different to how it is now, of course. There were skyscrapers, sure, but there were also |
| 1:44.9 | horse-drawn wagons. Jobs are scarce at this time. Wages are low and the law is uneven to say |
| 1:53.7 | the least. It's easily bent by the right bribe. Factories and warehouses hide forbidden alcohol-making operations. |
| 2:03.6 | Basements echo with the clatter of crates being loaded onto waiting trucks. |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from redrumpodcast, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of redrumpodcast and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.

