The Queen of the Mountain Moonshiners: The Story of Maggie Bailey

And we continue with our American stories. Steve Earle’s 1988 hit single, ‘Copperhead Road,’ tells the story of the bootlegging Petamore family and his son who takes a decidedly more mellow root after two tours of duty in Vietnam. While the story of the Pedomore family is pure fiction, the story of Moonshine Mama, a.k.a. Maggie Bailey, is not. You going to tell? The story? Is J.D. Phillips of the remarkable YouTube channel, The Appalachian Storyteller. Take it away, J.D.!

In many ways, Maggie Bailey was your typical mountain girl, growing up on Pine Mountain just north of the Virginia-Kentucky border. He was born in 1904 on this rocky hillside farm where Paul barely scratched out a living from the poor rocky soil. Now, money was scarce back in those days, haul across the mountains, and there was only a few ways that hillfolk could get their hands on some. One way, well, that was selling blockade corn liquor. And with so many miles of feed, Maggie’s Paul did what he had to do to make hens meet. So from a young age, Maggie spent many a night standing barefooted on the top of a split-bottom chair with a long wooden paddle, stirring her PAW’s mash and keeping the firebox stock with plenty of firewood. Little did she know, but her PAW’s nightly schooling on the fine art of crafting White Mule would end up defining her life. By 1921, Maggie was seventeen. Now, these were exciting times. The newly built railroad brought strangers from all over America. Maggie met a professional gambler and a coal businessman who dressed in fancy suits and even had the first pocket watch that the young girl had ever seen in her life. She told him about a business plan that she had thought of, and it was sure to make her a fortune if she only had an investor. Although the businessman was reluctant, Maggie had a way a bout her, and she eventually convinced him to give her thousands of dollars to fund it. You see, coal towns were literally springing up all over the county nearly overnight, and Maggie had taken notice of the thousands of brawny men that the railroad brought in each month. These same men emerged from the dark coal mines each evening with a powerful thirst for something to knock the dust out of their guzzle. But you see, a new law had recently swept across America, making alcohol illegal across the nation, called Prohibition, and that’s where Maggie’s plan came in. She knew exactly how to make her daddy’s White Lightning even better.

During this time in history, the law frowned heavily on arresting women. Heck, it was illegal to even search a woman, and if a fellow did arrest a woman and bring her into court, the jury just knew that no woman was capable of committing a felony, and she’d quickly be released and the chart is dropped. Indeed, it was the perfect plan, and she quickly rented a house on the outskirts of town, where she turned it into a moonshine factory capable of producing hundreds of gallons of untaxed liquor at a time. Before long, she had a monopoly on the entire market, and for the most part, no one had a clue that a sweet young lady was making all this potent for the entire length of Prohibition. Maggie Bailey’s moonshine reined supreme in Eastern Kentucky, but the sudden end of Prohibition threatened to shut her operation down. Nearly overnight, legal taverns and distilleries sprang up selling tax liquor, and most folks thought this was the end of Maggie’s operation, since only men were allowed to own liquor businesses. Yet Maggie was now 31 years old, and she had been running liquor for fourteen years as an independent businesswoman. She wasn’t about to just give up and quit, so she did something unthinkable. Maggie Bailey became the first woman to obtain a legal liquor license. They named her business ‘Meg’s Place.’ Oh, she could sell legal red whiskey just as good as any man, but the folks in Appalachia, what they wanted was good old moonshine, and before long, Maggie Bailey was selling legal whiskey out the front door and Mountain Dew out the back, all the way through the Great Depression. Her business thrived so much so that eventually federal revenue officers wanted to have a look-see and what made ‘Meg’s Place’ so special. In 1941, armed with a search warrant, federal agents burst in and seized 150 gallons of moonshine and promptly sentenced Maggie Bailey to two years in federal prison.

On the day Maggie was to report to prison, she first stopped by her sister’s house to tell her goodbye, and she also left a suitcase there and told her she’d pick it up when she got out. Just like that, they hugged, and Maggie spent the next two years locked behind bars. She put that time to good use. That’s right. She spent the entire time incarcerated studying the law, particularly the Fourth Amendment, dealing with search and seizure. She became an expert on that law, determined to never get caught red-handed again. By 1945, Maggie was back on the streets and up to her old habits again. The first thing she did was stop by her sister’s and pick up that suitcase, oh, which just happened to have eighty thousand dollars cash in it. She used that money to buy a house on the outskirts of Harlan with the intent on reopening her business. Yet there were two problems. The first was that she could no longer get a liquor license because of her felony, and the bigger problem was that Harlan County was now a dry county. But you see, she quickly hired several runners who would make daily trips back and forth to neighboring counties, returning each time with trunks full of beer, wine, and whiskey. ‘Meg’s Place’ was business, and this time operating more as a drive-through. Folks would simply pull up into the backyard, place the roorder, and off they went. For nearly three decades, ‘Meg’s Place’ sold illegal liquor seven days a week, and the law was furious and desperate to stop her. During the 1940s and 1950s, ‘Meg’s Place’ was rated 62 times, and each time the law would find liquor in different places, mostly hidden in junk cars or various outbuildings, and each time she was arrested, the charges would be dropped because the search warrants wouldn’t specifically authorize the search of her new hiding place, and even when the law had solid evidence, the jury would simply find her not guilty.

You see, by now, Maggie Bailey was an older woman and had become a pillar of the tight-knit community. She had paid for college for several of her neighbors’ kids. Maggie knew every one of her customers. Each visit to her house, the visitors would have to set a spell as she asked how your mama was doing and when when was the last time your daddy came to town. Still, police raids continued all the way through the 1960s, and in 1965, a routine raid on ‘Meg’s Place’ resulted in a discovery that would make headlines all across the nation. A score of deputy sheriffs and highway patrolmen were busy confiscating over 200 cases of beer and 50 cases of whiskey when one cop decided to have a look in Maggie’s closet. Hidden down in a corner, he saw fourteen brown paper bags and a dozen old socks, and wouldn’t you know it, every one of them was filled with one hundred dollar bills. The cops claimed that there was $480,000 cash hidden in her closet. “Oh, that’s hogwash!” Maggie claimed. “It was only $372,841 and not a penny more. I know, since I counted every single night.” You see, aside from helping others, Maggie had saved every dime she had ever made. She never bought clothes from anywhere, and she only wore secondhand clothes from her sister. She had never owned an automobile or even went to a movie. Even with all that money, she still kept hogs and chickens and a milk cow and raised all her own food. Yet the IRS quickly took note of the large pile of cash, and they also noticed that Maggie had never paid income tax, so they sued her for $1.37 million. But the IRS was about to find out what the local police already knew. You couldn’t beat Maggie in court. Astonishingly, Maggie was able to negotiate all the way down and paid only $18,000 in a settlement. The law had pretty much given up on stopping her. Every time she was arrested, the sweet old lady would show up in court with her printed dress and her baby blue sweater, and the charges they would be dropped, so ‘Meg’s Place’ kept right on raking in the dollars all the way through the ’70s, the ’80s, and even the 1990s. Maggie Bailey had began her moonshine career at the tender age of seventeen and continued to sell White Lightning and bootleg liquor all the way until she was 95 years old, a career of 78 years, and.

A special thanks to J.D. Phillips and his remarkable YouTube channel, The Appalachian Storyteller, and what a story he told about a Harlan County, Kentucky, legend, an Appalachian legend, the story of the Moonshine Mama, Maggie Bailey, here on Our American Stories.