During the 1920s and early 1930s, the U.S. found itself in the grip of prohibition. This was a nationwide ban on the production, sale, and transportation of alcoholic beverages. But rather than eliminating the demand for alcohol, it gave rise to secretive and dangerous crime, the world of bootlegging. Smugglers and inventive entrepreneurs sprang into action, navigating the lawless landscape to make some good money. This was the era after the Wild West, marked by crime and secrecy, and we’re here to share it with you. Here are 20 vintage photos of bootleggers in action during Prohibition.
1. These bootleggers were from St. Paul, Minnesota, in 1921.
These two look like they’re up to no good. It’s wild to think these two supplied so many people with booze during prohibition.
2. The Charlie Birger gang.
These guys were famous bootleggers, but they were even more famous for chasing the KKK out of Williamson County, 1925.
3. The classic sign of a bootlegger.
I mean if this actually worked more power to him. Unfortunately, any smart cop would see right through it.
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4. I wouldn’t drink anything from a place that looks like this.
I’d rather not drink bits of dirt and sawdust. You just know this place didn’t have a cleaning staff.
5. Nothing smuggles liquor like a Chevy.
Pictured is Julia Burnell, a 15-year-old bootlegger from Detroit. Her parents bought her a Chevy with the sole purpose of smuggling booze for them. Those are some cool parents.
6. That’s a lot of bottles to smuggle.
So you’re telling me, that all 250 of those bottles of tequila fit inside that little gas tank?
7. Why is it that people always take incriminating photos?
It’s cool and all, but now there is literal proof that you were taking part in illegal activity.
8. That’s a flask?
This woman who was about to be arrested for being a bootlegger, is showing her enormous liquor flask she carried with her before being taken in. Can you fit enough booze in there ma’am?
9. It’s funny that they make the criminals take a photo with the contraband.
This is utterly embarrassing. First, you get caught with liquor, then the police force you to take a picture with them and the illegal alcohol. They’ll never recover from this.
10. The law, and the local bootleggers.
As you can see, there was no corruption in the ’20s. Just kidding, these boys definitely supplied that cop with weekly bottles of liquor.
11. This is one of the best hiding places we’ve seen.
This secret compartment for alcohol is one of the smartest moves from a bootlegger I’ve seen. These guys were true professionals.
12. That’s a lot of dumped booze.
During prohibition, the government deliberately poisoned the alcohol bootleggers were stealing. 10,000 people suffered fatal bodily injury.
13. Nothing to see here, just loading a couple of suitcases into my car.
If you want to seem inconspicuous, don’t dress like a total gangster. A cop would see these guys as bootleggers a mile away.
14. The cops don’t even look slightly disappointed.
Today cops at least look happy to make a big bust. These guys look sad to have to confiscate all of this booze.
15. These prohibition agents are destroying this bar.
Smart agents would follow a bootlegger to his deliveries and shut down the speakeasy he delivered to.
16. A test vote on prohibition in Wahington D.C.
You can bet that line is full of thirsty customers and bootleggers.
17. Bootleggers had to help cops dump the contraband.
That’s a rough story, they spent time and effort making this alcohol for others to enjoy, and they ended up having to dump it while cops gave them smug looks.
18. Yeah that’ll make you seem less guilty, travel with Tommy guns.
There’s no easier tell of a criminal than automatic weapons in the car. These guys are holding a sign that says, “we have illegal alcohol.”
19. All the outlaws and bootleggers headed to the bars the night prohibition ended.
I’m curious if they released all of the bootleggers and criminals from jails that were incarcerated for alcohol-related crimes.
20. That guy on the right looks like he wants to put his head under that flow.
The amount of corrupt cops had to be insane. I wouldn’t be surprised if someone was down in that sewer with another bucket to catch the booze.
