Women Bootleggers and Women Prohibition Agents

Women bootleggers were often very clever. A good example is the Henhouse Bootlegger. You’ll learn about her shortly.

On the other hand, women prohibition agents could be very effective. You’ll discover how and much more below.


I.   Women Bootleggers

II.  Women Prohibition Agents

III. Summary

IV.  Resources

I. Women Bootleggers

Women bootleggers enjoyed many advantages over men. Many states had laws protecting women from search. Sometimes they would hide alcohol on themselves and taunt police to search them. They threatened to sue officers if they did.

Some thought there may have been far more women than men who were bootleggers. They may have sold as much as five times the number. A female agent said that they were much harder to detect than men.

Juries were also reluctant to convict mothers and grandmothers of bootlegging. Thus, they were much less likely to suffer from their illegal acts.

Big Profits, Light Punishments

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, Esther Matson, to attend church every Sunday for two years. The President of the US pardoned a Michigan woman bootlegger. Similarly, the governor of Ohio reduced a woman bootlegger’s sentence to only five days.

women bootleggers
Women Bootleggers

Officials were less likely to suspect women of bootlegging. 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.

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

Bootleggers sometimes hired women simply to ride along. Police were less likely to stop and search the vehicle. One newspaper reported that no “self-respecting” prohibition agent liked to stop a vehicle with a woman in it.

She was a moonshiner, but he loved her still.

A Few of the Many Women Bootleggers

Maggie Bailey

Maggie Bailey of Clovertown, KY, was the “Queen of the Mountain Bootleggers.” She began bootlegging during Prohibition at age 17. 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 US District judge described her as an expert on search and seizure laws.

Stella Beloumant

Stella Beloumant was the leading bootlegger in Elko, NV.  Her case warranted an entire task force. It included the US 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 arrest netted an enormous quantity of bootleg.

Bertie (Birdie) Brown

Bertie (Birdie) Brown was an African American woman who homesteaded in Fergus County, MT. She made moonshine that was the “best in the country.” She died from burns when her still exploded in 1933.

Esther Clark

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

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 US. Officials seized it with 10,000 cases of Scotch. After that, she and her ships were constantly under suspicion of further bootlegging.

Josephine Doody

women bootleggers
Josephine Doody

“The Bootleg Lady of Glacier Park,” Josephine Doody was a former dance-hall worker. Her best customers were railway workers. A train would stop at Doody siding. Each toot of the horn indicated an order for one gallon of moonshine.

Nora Gallagher

Nora Gallagher was a widow in Butte, MT. She brewed in her kitchen. Her explanation was that she needed the money. And for what purpose did she need money? She said it was to buy Easter outfits for her five children.

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 FL playing tennis and having a “great time.”

Lavinia Gilman

Lavinia Gilman was an eighty-year-old woman. But she was running a three-hundred-gallon still. The judge who heard her case didn’t think she was the “real culprit.” Perhaps he was sexist. In any case, he preferred to believe that it was really her son.

Mary Ann Moriarity

Mary Ann Moriarity washed clothes for residents living in a boardinghouse. Then she had her teenage daughter deliver the moonshine hidden among the clean clothe. She charged fifty cents for a pint and two dollars for a gallon.

Willie Carter Sharpe

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

Mary Wazeniak

Moonshiner Mary Wazeniak was a Polish immigrant in La Grange Park, IL. She made and served moonshine out of her home. At the end of a night, one of her customers was staggering home. He fell into a bog and died from the toxic brew. At her trial, the press called her “Moonshine Mary.”

women bootleggers
Mary Wazeniak

Diversity of Women Bootleggers

Barely four years into Prohibition, journalist Jack O’Donnell described women bootleggers. He said they come from all ranks of life. They come from slums. From palatial homes. They come from across the country.

He also wrote this. “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.”1

How right he was.

II. Women Prohibition Agents

Women Prohibition agents could be uniquely valuable. That’s because many states had laws preventing male agents from frisking or otherwise searching female suspects. And even if they didn’t, convention prohibited it.

Women bootleggers would sometimes hide alcohol on themselves and taunt male agents. An Ohio “Dry Agent” described such an event to the Hamilton Evening Journal in 1924. “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.”2

Bootleggers would often hire women to ride with them when transporting alcohol. “‘No self-respecting federal agent likes to hold up an automobile containing women,’ according to The Boston Daily Globe.”3

Although useful in law enforcement, there were never many female Prohibition Bureau agents. The Bureau hired a dozen in 1922.4 It added others soon after.5

Two Pioneer Women Prohibition Agents

Georgia Hopley

Georgia Hopley being sworn in as a Prohibition agent

Women Prohibition Bureau agents played varying roles. After Georgia Hopley became an agent, she worked in local enforcement in DC. She then developed, implemented, and lead the Bureau’s publicity efforts.

Georgia Hopley became a one-person public affairs office. She traveled across the country. She spoke at churches, schools, and other groups. Agent Hopley wrote newspaper articles and gave interviews. She discussed prohibition enforcement problems with politicians. And with business leaders. Her job was to strengthen public support for the enforcement of Prohibition. She worked on that with determination and persistence.6

Daisy Simpson

Daisy Simpson’s official Prohibition Bureau ID.

Much more visible was Bureau Agent Daisy Simpson. Her home base was the San Francisco office. However, she also worked in other cities across the country.

Early on, Daisy Simpson received much coverage in the press. They called her the ‘Lady Hooch Hunter.’ She often used disguises. She had a hundred different ones. Often, using a disguise, she would spend a few nights in a speakeasy, hotel or restaurant. Then she would arrest those who served her any alcohol.


In her use of disguises she was similar to the well-known Izzy Einstein & Moe Smith. Like them, she was clever. She would pretend to become ill outside speakeasies. Then she would arrest bartenders who would bring whiskey to help her.

Daisy Simpson was responsible for the seizure of 8,000 gallons of wine in a single raid. But most of her arrests were for petty crimes.

Daisy Simpson’s application to become a Prohibition agent.

For example, she arrested a bellboy who brought her medicinal whiskey. That was after she’d complained about stomach pains. She arrested a man who had a single jug that “smelled like moonshine.”

Several judges chastised her about the trivial offenses for which she would arrest people. Judges also had to dismiss many cases because of her illegal entrapments. More important, the Bureau wanted to arrest major moonshiners and bootleggers.

Former Delinquent

Daisy Simpson had been a delinquent in her youth. She had spent much of her time in dingy bars and hanging around criminals. In addition, she was doing illegal drugs. She then reformed and joined the morals squad of the San Francisco Police during World War I.

Simpson left the Bureau because she became ill and confined to bed. She relapsed and again began using illegal drugs. In TX police arrested her for receiving drugs through the mail.

She became deeply depressed. It was over her failed marriage and her destroyed reputation. Having managed to smuggle a gun into jail, she shot herself in the stomach. She failed to kill herself but the wound became infected.

After a long, painful recovery, she borrowed money to bail herself out of jail. She pled guilty and received a suspended sentence. Simpson then returned to CA and back into obscurity.7

III. Summary

Both Georgia Hopley and Daisy Simpson served the Bureau. But both did so in different ways. And both came from very different backgrounds. Hopley’s father was a newspaper publisher and her brother was a senator. On the other hand, Simpson’s family appears to have been of very modest means.

After their service with the Bureau they followed very different paths. Georgia Hopley continued with civic activities. Daisy Simpson sank into anonymity.

A baseball team needs players with very different skills. Similarly, the Bureau needed agents with very different skills. It found those in both Georgia Hopley and and Daisy Simpson.

IV. Resources: Women Bootleggers


Resources on Women Prohibition Agents

    • Death Ends Career of Georgia Hopley. Toledo Blade, July 1, 1944, p. 2.
    • Graham, L. Governor’s Wife Demands Women Prohibition Agents. The Spokesman-Rev, May 12, 1923, p. 20.
    • Mrs Hannah Brigham Appointed Prohibition Agent. Cambridge Trib, Feb 4, 1922, p. 1.


1. O’Donnell, J. The ladies of Rum Row. Am Legion Week, May 16, 1924, pp. 1-9.

2. Minnick, F. Women’s History Month.

3. Minnick, ibid.

4. Women Dry Agents Named. New York Times, May 7, 1922.

5. More Women Prohibition Agents Appointed. Eve News (Harrisburg, PA), Oct 6, 1922.

6. Untitled article about Georgia Hopley. AFT, March 24, 2016.

7. Kratz, J. On Exhibit: “Lady Hooch Hunter.” Nat Archives, April 7, 2015. Genthon, M. Prohibition Part Two. Women on the Frontline – Daisy Simpson. CT Women, Sept 8, 2015. Tragic Ending to Woman Dry Agent’s Career. Daisy Simpson, Held on Drug Charges, Is Dying. Lewiston Eve J, March 22, 1926, p. 7. (Despite story, Simpson survived.) Funderburg, J. Bootleggers and Beer Barons, pp. 291-294.

Web Pages on Bootlegging in General