Nice boots there partner.  They look like something a bootlegger might have worn back in the day.  Grab a barstool, and I’ll reveal what I can about bootlegging.

  • It’s All in the Name

It all began when people discovered that the top end of a tall boot proved to be a IMG_1371convenient hiding place for things such as weapons, a flask, money, or even an extra ace card during the 17th century.  It probably began sooner, but for the sake of the story, that’s where we’ll start.  This part of the boot is called the bootleg, and the act of concealing an object in the bootleg with the intention of it going undetected became known as bootlegging.  Little did we know that bootlegging would later become such a large and glorified topic in our nation.

In the mid, to late 1800’s some states such as Maine, Vermont, and Kansas attempted to enforce dry laws, even before the whole nation underwent its period of prohibition.  A Kansas judge used the word bootleggers to describe men who were smuggling illegal liquor into his dry county in 1890.  Several decades later, after America underwent its “noble experiment,” Prohibition, the act of bootlegging saw a huge surge, and things started to get really interesting.

  • Cat and Mouse

As stricter laws were put in place across the nation, outlawing the transportation of beer and liquor, the federal government provided guns, vehicles, and training to 1500 agents called Prohibition officers, or better known as “Prohis.”  However, due to lack of funding and little to no support from the state and local governments, this attempt at stopping the movement of alcohol by such a small force seemed doomed from the start.  That didn’t stop these few brave men from trying.

Transporting illegal booze, on the other hand, quickly became a large and profitable enterprise, and getting caught meant a loss of income or jail time for the handler.  Therefore, even with such a small task force on the lookout for them, “bootleggers” still weren’t taking any chances of getting caught.  Their tactics quickly evolved, improved, and became more creative.  The games had just begun.

Bootleggers deliberated on new, more creative ways of avoiding detection from the authorities.  Some started hiding the alcohol in different parts of their vehicles.  Parts as basic as false door panels or sometimes as complex as a faux lumber truck hollowed to conceal larger loads.  Some bootleggers hid there shipment inside other products such as bags of flour, tobacco, and building materials.  Some went as far as to hide the liquor inside deceased animals on their way to the butcher.


A 1929 Auburn at The National Auto & Truck Museum in Auburn, IN

The Prohibitions officers faced a difficult task enforcing such large and widespread acts of this criminal behavior.  For a few, however, it became almost an obsession.  Two agents in particular named “Izzy and Moe” became famous for their tactics and ambition in stopping the illegal alcohol trade, and deceit was their game.  To catch the bootleggers they disguised themselves as anyone from gas clerks, to football players, even as women.  After they became famous among criminals they even made arrests just telling their targets they were themselves, knowing they wouldn’t believe them.  The improv and commitment of the duo ended up earning them nearly 5000 arrests in cities all across the nation.

  • All About the Benjamins

In the end, however, the task of enforcing the law became too great for most Prohis.  There were just too many people engaged in the activity, and bootleggers quickly learned that many officers had a price.  With the booze money they were raking in, it was affordable enough and worth it to pay off the law.  Bribery and corruption became rampant, and many officers with their small government salaries ended up on the payroll of gangsters who employed them as informants or lookouts.  In the end, the only thing that could stop bootlegging was repealing the laws making it illegal.  Leaving us with one wild story related to the anatomy of a boot.

Well, I think these boots are ready to start walking.  I think I’ll take my tab and part ways.  Until next time partner.



  • All The Sneaky Tricks of Prohibition Bootleggers

  • Prohibition Agents Lacked Training, Numbers to Battle Bootleggers

6 thoughts on “Bootlegging

  1. I remember hearing at one time that the bootleggers, particularly in the South, were the early start of organized automobile racing and you can trace NASCAR’s lineage back to people running alcohol from state-to-state. Have you come across anything like this?

    Liked by 1 person

    • Yes I have heard a little about that. There are so many stories and facts on the subject I ended up just giving the skeleton version of the story. It was also illegal to search a woman back then, so they ended up playing a huge role in smuggling booze, but I just missed women’s week and cut it out… Sorry ladies.

      Liked by 1 person

  2. Pingback: The Versatile Blogger Award – Bitchin’ in the Kitchen

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