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A Hooch 'n Hellraisers blog post: Entrepreneurial women thriving in Prohibition America

Barely four years into Prohibition, journalist Jack O’Donnell described women bootleggers. They “come from all stations and ranks of life—from the slums of New York’s lower East Side, exclusive homes in California, the pine-clad hills of Tennessee, the wind-swept plains of Texas, the sacred precincts of exclusive Washington. … Some are bold, brainy and beautiful, some hard-boiled and homely, some white, some black, some brown. All are thorns in the sides of Prohibition Enforcement officials.”
Oh, how right he was.

Going into effect in 1920, America’s Eighteenth Amendment prohibited the manufacture, transport, and sale of alcohol in the United States. Lasting thirteen years, this era was commonly known as Prohibition. As soon as it started, so did bootlegging.

It is difficult to quantify how many women participated in bootlegging. However, the number of women arrested under Prohibition laws suggests it was a widespread practice. More women were charged with federal crimes than ever before. A federal prison specifically for women was built in West Virginia in response to the so-called crisis.

Women were so good at bootlegging that prohibition agents of the time estimated that women outsold men five to one.

An opportunity ripe for exploitation:

There was a lot of money to be made in selling illegal liquor in the United States during the 1920s. One enterprising woman who owned a boardinghouse in was caught selling alcohol to her patrons. Her record book showed that for the previous few weeks, her salary had averaged $150 per day. In 1924, the average (white male) yearly income in the country was around $1,300, so a woman making that much in two weeks through illegal alcohol production points to a lucrative black market.

Changes in transportation technology during the 1920s boosted women’s access to many new economic and social opportunities, including those around alcohol.
Not many women could drive a team of horses or even had access to them, but a car? Thank you, Henry Ford, for making the automobile available to many more Toms, Dicks, and Harriets. This newfangled invention provided women with the mobility and the means to transport illegal hooch.

A fast car was the most essential piece of equipment for the bootlegger who traveled overland to deliver the goods. Even more than a gun, bootleggers relied on their automobiles. It had to be able to safely haul the hooch over bad roads and rough terrain and outrun the cops.

New women’s fashions in the 1920s also lent themselves to clever ways to smuggle alcohol. Feisty dames and flappers with freshly bobbed haircuts could spend their evenings dancing the Charleston in dance halls and speakeasies, sneaking in flasks of liquor on garter belts, under oversized fur coats, or in avant-garde styles of skirts and blouses. And there were few male prohibition agents or cops with the nerve to check what those damsels were wearing underneath.

“A painted-up doll was sitting in a corner. . . . She had her arms folded and at our command she stood up. But then came the rub. She laughed at us . . . then defiantly declared to bring suit against anyone who touched her,” an unnamed Ohio “Dry Agent” told the Hamilton Evening Journal in 1924.

Bootleg Queens:

While many of female bootleggers were operating on the scale of a home-based business, there were other pistol-packing dames who commanded empires and were known as Bootleg Queens.

“Women rum runners equipped with limousines and daring enough to use guns.”
Every area of the country had at least one bootleg queen.

Maggie Bailey

Maggie Bailey of Clovertown in Harlan County, Kentucky, was the ‘Queen of the Mountain Bootleggers.’ She began bootlegging during Prohibition at age seventeen. The “Queen” lived simply and often gave food and other help to families in need. Because of this, juries often looked kindly on her. A U.S. District judge described her as an expert on search and seizure laws.

Maggie’s title “Queen of the Mountain Bootleggers” was well deserved. Born in the state of Kentucky, she started bootlegging at the age of seventeen. Despite being caught several times, the court never issued a genuinely strict punishment for Bailey.

Hilda Stone

In Western Massachusetts and Vermont, the honor of the title ‘Bootleg Queen’ fell to Hilda Stone. A housewife who earned extra money working as a stenographer, she was known around town as a fashionable woman. With her hair bobbed and a confident smile, she was a popular customer in the local speakeasy.

Initially, it was reported that she turned to a life of crime as a means of survival. Her husband’s lumberyard had fallen on hard times and was close to bankruptcy. The Minneapolis Star ran a large photo of her on its front page, with a story that proclaimed: “Love for her husband and a mad resolve to help him out of a financial squeeze in his lumber business prompted Mrs. Hilda Stone … to abandon housework and a life of respectability and turn bootlegger.”

Hilda decided that the family business needed a cash infusion. Using the family car, she headed north to Canada and began smuggling liquor for the local speakeasy. She was a natural, and it wasn’t long before she had expanded her territory to include Vermont, New Hampshire, even as far away as Boston.

To keep up with demand, she had to increase supply. She modified her car with secret compartments, betters shocks, a souped-up engine, and scattered packages from ladies’ dress shops in Canada across the backseat.

The expanded business also meant she had to hire help. According to border patrol agents, Hilda became the field lieutenant for a gang run out of Greenfield that nicknamed her the “queen of the border rum runners.”

Stone first made headlines in August, 1925, when she pulled a gun on a state trooper during a traffic stop near Jacksonville, Vt. The car, driven by an employee of her husband’s lumberyard, was filled with 174 quarts of illegal hooch they just had smuggled over the border. She made bail and was soon back in business.

Stone was arrested again in September and once again made bail, arrested again in October and once again made bail, and finally was arrested again in December.

However, the December arrest was different. A thorough search of her car revealed the secret compartments, but they were empty. They had to let Hilda go but police seized her car.

Eventually, Hilda Stone served a six-month jail sentence in 1926. But as soon as she was out, she again started running liquor over the border.

Her border-running exploits and arrests were chronicled by newspapers well into 1928. She was quoted as saying “she liked to run liquor across the border for ‘the thrill of it’ and thought it rather fun ‘to be pursued by the border officers’.

Stella Beloumant

Nevada’s Bootleg Queen was Stella Beloumant and she was responsible for one of the largest bootlegging operations in the state. The size of her operation and her wide-spread notoriety drew the attention of the Federal Government. Eventually, her case warranted an entire task force which included the U.S. Attorney General, the Prohibition Bureau‘s second in command plus two of its agents, and the district attorney. The sheriff’s office put her under 24-hour stakeout.

Her eventual arrest netted 820 gallons of wine or the equivalent to 4,140 bottles.

Gloria de Casares

Gloria de Casares was bootlegging wife of a wealthy Argentinean. In 1925, her five-masted ship was preparing to depart from London to the U.S. Officials seized it with 10,000 cases of Scotch. After that, she and her ships were constantly under suspicion of further bootlegging.

Birdie Brown and Josephine Doody’s stories are covered in the Moonshining blog post of the Hooch ‘n Hellraisers series.

Edna Giard

Edna Giard married a man she knew was a bootlegger. They moved alcohol for Al Capone from Chicago to states in the upper Mid-West. She loved the money, excitement, and glamor. Once she spent the afternoon with Capone’s wife in Florida playing tennis and having a “great time.”

Willie Carter Sharpe

Willie Carter Sharpe was a bootlegger in Franklin County, Virginia. She hauled more than 220,000 gallons of moonshine between 1926 and 1931. At her trial, spectators focused on the diamonds in her teeth.

Cleo Lythgoe

However, the greatest female bootlegger was Gertrude “Cleo” Lythgoe, a legitimate licensed liquor wholesaler in Nassau, Bahamas. A majestic-looking woman, Cleo was mistaken for Russian, French and Spanish, but she was American with ties to a British liquor distributor.
When Prohibition became law, she moved to the Bahamas and used her Scotland connections to import the best Scotch. In the Bahamas, this liquor was loaded on the boats of the real Bill McCoy and brought into the U.S. liquor supply.

But Cleo eventually moved into commissioning her own boats – that’s where the money was, after all. Bootlegging also came with greater risk.

Cleo became a target of the U.S. authorities and was even stripped searched by a female officer at a port. Like many other so-called Queens of the Bootleggers, Cleo loved the limelight and became a true media darling with newspapers from Jamaica to New York publishing her photo. Men fell in love with her and sent “love letters” to the newspapers. An Englishman, who simply signed “One Who Loves You,” wrote: “I only wish you lived in England. I would marry you, as a home life would be far more suitable for you than your present occupation.”

The Wall Street Journal estimated she was worth more than $1 million, but nobody really knows. Cleo was cryptic and never incriminated herself about her illegal dealings.

I fictionalized Cleo in the Rum Runners’ Chronicles series. She was one of the three legs of the Liquid Gold Triangle, along with Edith Duffy and Spanish Marie.

But they weren’t all queens:

Popular media of the time often portrayed bootleggers as mobsters or glamorous speakeasy matrons. While such people existed, most bootlegging happened on a much smaller scale.
For working-class families, selling alcohol provided a necessary second income.

Women were active participants in this home-grown industry. While men were outside the home working, women could manage a liquor enterprise while completing their other at home responsibilities. Some women distilled liquor in their homes on a small scale; others sold liquor acquired through larger smuggling operations.

Esther Clark was a bootlegger in rural Kansas. She stored moonshine in her chicken coop. For this reason, she was the Henhouse Bootlegger.

Because many bootlegging operations were family affairs, children often participated as well. The hero of my Moonshiner Mysteries series started out working in the Bailey bootlegging business, giving Maggie Barnes the ride of her life as they flew along the dark back roads around Philadelphia.

Helen McGonagle Moriarity recalled her role in her mother’s liquor trade, which was cleverly paired with her existing laundry business. Moriarity’s mother, Mary Ann, washed for miners living in a boardinghouse. As a teenager, Helen delivered booze hidden among the clean clothes for “fifty cents a pint and two dollars a gallon.”

The Feminine Advantage

Woman had an advantage over men when it came to moonshining- rum running- bootlegging. For starters, they were much harder to detect and arrest than men simply because it was illegal to search a woman in those days. Women took full advantage of this and actually hid moonshine on their persons; some even taunted law enforcement to search them.

Also in their favor was the fact that juries of the day were loath to convict a woman of the crime of bootlegging. They simply refused to believe that a woman could do such a thing or had the stomach for putting mothers and grandmothers behind bars.

In 1925, a woman in Milwaukee admitted earning $30,000 a year bootlegging. That’s over $400,000 in today’s dollars. The court only fined her $200 and gave her to a month in jail.

Another court sentenced a 22-year-old bootlegger in Denver, Esther Matson, to attend church every Sunday for two years. The President of the U.S. pardoned a Michigan woman bootlegger. Similarly, the governor of Ohio reduced a woman bootlegger’s sentence to only five days.

Police arrested Susie Gallagher Kerr along with two men. She admitted that the still they found was her operation, yet they refused to believe her and convicted the two men instead.
Mobsters and alcohol smuggling syndicates took advantage of these legal loopholes, recruiting women into their ranks and employing them to bootleg liquor.

And even if the gangs didn’t hire women as actual bootleggers, they hired them for ride-alongs. Preferring pretty girls over Plain Janes, the women road along as cover, reducing the chances of getting searched. The word on the street was that no decent federal agent or cop would hold up a car that had women in it.

Women bootleggers tended to keep a lower profile. They were less likely to boast or to become confrontational. And in any conflict with police, they were much less likely to be a target of gunfire.

Other blog posts in the Hooch ‘n Hellraisers series:




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