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Female Bootleggers of the Prohibition Era - The Women that Made it Possible

Bootlegging women of the Prohibition era

The rise of a religious renaissance starting in the 1820s and 30s was an early catalyst of the 18th Amendment, which banned the manufacture, transportation and sale of intoxicating liquors in 1919. By the early 1900s temperance societies were pervasive in U.S. cities and towns, with large numbers of support from women who often viewed liquor as detrimental to family life.

Shortly after Prohibition was enacted, the illegal creation and distribution of liquor started, and speakeasies became commonplace. From small bootlegging operations, to large mob rings, many profited from the illegal pastime — and the ladies were not to be left out.

The unlikely bootlegger

While bootlegging was considered a male-dominated trade, there were certainly ladies in the game. Not all women of the 20s were dancing the Charleston in their flapper attire. Some were helping hooch get from here to there. 

As an unlikely suspect for police, there were advantages for female bootleggers. They enjoyed certain privileges based on societal norms of the time. Not only was it illegal in many states for male police officers to search women, it was a great insult to even imply that a woman could be capable of such horrific crime like bootlegging.

In a similar vein, ladies were simply quite handy to have around. They were great road trip companions for bootleggers. It was not polite to stop a car with a woman in it and most law enforcement respected that custom. 


As bootlegging rings grew, so did the number of women involved. The savvy criminal knew the legal protections women enjoyed and began to recruit them into their organizations. It’s suspected that at one point women outnumbered men in the profession at a five to one ratio.

When women were brought up on charges, they also found favor in the court. Politicians and judges weren’t keen on convicting someone’s auntie.

What is a bootlegger?
A bootlegger is a person who sells, transports or makes alcohol unlawfully. A practice that was rampant during U.S. Prohibition of the1920s and early 30s.
How did bootlegging start?
The Eighteenth Amendment banned the manufacture and transportation of alcohol. After it was signed into law, Bootlegging was an almost immediate reaction. It is often described as the birth of organized crime.

Money maker

A good living could be made by bootlegging ladies. One Milwaukee woman admitted to earning $30,000 a year in 1925 - that is the equivalent of nearly $428,000 in 2018. She was sentenced to a month in jail and ordered to pay a $200 fine. With minimal punishment and such great financial reward, the profession of liquor production and distribution was quite attractive.  

Most women worked as bootleggers simply to make ends meet. Living to the age of 101, Maggie Bailey was one such woman. She enjoyed making her white moonshine (which was not legal even after Prohibition) so much that her career lasted nearly 90 years — in Harlan County, Kentucky at that. A dry county where she was only convicted once in all that time. You see, she’d come into courtrooms reminding most people of their grandmothers with her gray hair and floral aprons. This wasn’t to deceive the court; that’s who she was every day.

The locals were quite fond of their “Queen of the Mountain Bootleggers.” While she began in the business to support her family, she became a benefactor to her community. After her death, in an interview with NPR Maggie's attorney Otis Doan shared, “Well, people in the community just loved Maggie. Maggie was the type of person that bought food for families if they were having hard times. She helped send people to school, to college in her community...to me Maggie was an asset to the community.”   


It seems Maggie was otherwise viewed as a standup citizen, but there were some women far more notorious in the Roaring 20s - we’ll get to them in upcoming posts. While women may have helped give rise to Prohibition, they most certainly helped keep bootlegging operations running and the hooch flowing as well. Join us as we explore the prominence, personalities and purpose of the ladies of bootlegging.  


Bootleg Bourbon Balls is a boutique bonbon shop specializing in spirited chocolate creations. We celebrate these notoriously naughty chocolates by hand-crafting them in small batches using a variety of Kansas City’s craft spirits. It’s quite certain bootleggers wish they had thought to conceal booze so deliciously. Take a trip to bootlegbourbonballs.com to get your infamous treat or unique, tasty gifts.