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This Day (An America 250 History Show)

The Bootletter Biplane Bombings [Some Sunday Context]

This Day (An America 250 History Show)

Jody Avirgan & Radiotopia

History

4.51K Ratings

🗓️ 18 January 2026

⏱️ 17 minutes

🧾️ Download transcript

Summary

For our "Sunday Context" series, we build on this past week's coversation about Prohibition with perhaps the most colorful story of bootlegging and liquor gangsters we've ever heard. In 1926, members of the Shelton gang in southern Illinois commandeered a biplane to drop homemade bombs on the hideout of their main rivals, the Birgers.

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Our team: Jacob Feldman, Researcher/Producer; Khawla Nakua, Transcripts; music by Teen Daze and Blue Dot Sessions; Audrey Mardavich is our Executive Producer at Radiotopia.

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Transcript

Click on a timestamp to play from that location

0:00.0

Hey there, welcome to this day. My name is Jody Avergan. And this is some Sunday context,

0:09.7

where we bring you new conversations and favorites from the archives to try and add a little context to what we've been covering.

0:16.5

Now, we just wrapped up our two-part episode on Prohibition as part of our 50 Weeks that

0:21.2

shaped America series.

0:23.0

We looked at the social and political forces that powered the temperance movement, how

0:27.2

the country actually tried to pull this off, and what happened once the law collided with

0:33.1

reality.

0:34.4

And you know, when we picture Prohibition, we tend to picture bigger cities, New York, Chicago, Atlantic City,

0:41.1

speakeasies, gangsters, that whole thing. But Prohibition didn't just reshape those urban centers. It

0:47.1

created black markets everywhere, and sometimes those markets turned into outright war.

0:53.2

So today we are going back into the archive for a story set far from the coast, rural

0:57.7

southern Illinois, and to my mind, it's one of the wildest prohibition stories ever told.

1:03.1

Now, before we bring you that story, a quick reminder that if you are a paying subscriber to

1:07.3

our newsletter, you get early access to our whole America 250 series, full video,

1:12.6

ad free in your inbox on Sunday afternoons, plus other extras that help support the show.

1:18.7

Go ahead and sign up for that at thisdaypod.com. Thisdaypod.com. Next up in our 50-week series,

1:25.5

we go to the Battle of New Orleans.

1:28.0

We talk about the War of 1812 and the arrival of one Andrew Jackson on the national political seat.

1:34.6

Anyway, for now, coming up after the break, bootlegging, gangs, and yes, aerial bombing.

1:40.5

Music bombing.

1:52.3

Hello and welcome to this day in esoteric political history from Radiotopia.

1:54.0

My name is Jody Avergan.

...

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