Women Bootleggers: The Women Who Kept America Drinking During Prohibition
Updated: Oct 5
In Butte, Montana, a widow called Nora Gallagher started brewing liquor on her kitchen stove because Easter was coming and her five children needed new outfits. Across town a teenager named Helen McGonagle was delivering clean laundry to miners with pints of her mother's moonshine folded inside it. And somewhere nearby an 80-year-old called Lavinia Gilman was running a 300-gallon still.
That's what most Prohibition bootlegging looked like. Forget the Tommy guns and pinstripes. It was a kitchen, a copper pot and a woman with bills to pay. Women bootleggers worked at every level of the trade, from back-door pints to ocean-going schooners, and for much of the 1920s the law had no real idea what to do about them.
Quick Answers
Were most bootleggers women? Nobody knows. A claim that women outnumbered men five to one circulated in the 1920s, but it can't be traced to any reliable count.
Why did so many women do it? Money. It could be done at home, around children, using skills they already had, and it paid far better than any legal work open to them.
Why were they hard to catch? In several states male officers weren't allowed to search women, and most were reluctant to even where they could.
Who were the best-known women bootleggers? Gertrude Lythgoe, Texas Guinan, Bertie Brown, Josephine Doody, Willie Carter Sharpe, Maggie Bailey and “Moonshine Mary” Wazeniak.
Did they get off lightly? Often, but not always. Mary Toia of New Orleans got a year and a day in federal prison, and Mary Wazeniak got one year to life.
Did women help end Prohibition? Yes. Pauline Sabin's repeal organisation signed up around 1.5 million women, roughly three times the membership of the main temperance union.
Why Prohibition suited women so well
National Prohibition began in January 1920. The 18th Amendment banned the manufacture, sale and transport of intoxicating liquor, but not the drinking of it, and that gap is where the whole illegal trade lived. People still wanted a drink. Somebody had to make it. (Winston Churchill got round the problem with a doctor's note, but that wasn't an option for most.)
Making it was, in most households, women's work already. Brewing, fermenting and preserving were kitchen skills, handed down from mother to daughter. A still could sit behind a wash boiler. The work fitted round children and didn't need a husband's permission or a bank's money. For widows and deserted wives, who had almost no way of earning a living wage, it was close to the only business on offer.
The historian Mary Murphy made this case in a 1994 study of Butte, and Montana Women's History has collected many of the stories. Butte was a hard-drinking mining town that had voted against Montana's own state prohibition in 1916. Mary Ann McGonagle ran a laundry out of a miners' boarding house and a still alongside it. Her daughter Helen did the deliveries, hiding the bottles in the clean washing, and remembered the price list decades later: “fifty cents a pint and two dollars a gallon”.
Others were less discreet. Distinctly Montana's round-up of the state's women bootleggers includes Mrs Steve Gregovich, who met the sheriff with a pitchfork and was never bothered again, and Annie O'Day, a widow caught with 250 gallons of mash who took her four children to California. The judge dropped the charges on condition that she didn't come back.
The money explains a lot. When Denver police caught a boarding-house keeper called Anna Butler selling drink to her lodgers, her own account book showed she'd been taking about $150 a day. The average American man was earning roughly $1,300 a year.
Six children and 130 bottles: the New Orleans evidence
The other detailed study is Tanya Marie Sanchez's work on New Orleans, published in the journal Louisiana History in 2000 and summarised by JSTOR Daily. Going through arrest and court records, she found that the typical woman bootlegger there was working class, often an immigrant, usually a mother and frequently divorced, separated or widowed. Bootlegging topped up a family income that wasn't enough to live on.
These women made beer, wine, whiskey and gin at home. Some ran it as a sideline to a grocery or a soda stand. Some ran speakeasies, bottling plants or delivery rounds. When police took 130 bottles of home brew from Marie Hoppe's house, she had her answer ready: “I have six good reasons for making beer. I have six small children.”
Sanchez's most useful point is about what the records can't show. For every woman who turned up in a court file, she argues, there were many more who were never caught and left no trace at all. That matters for the next question.
Did women really outnumber men five to one?
You'll see it stated as fact all over the internet that women bootleggers outnumbered men five to one. The original version of this article said so too. It's worth being straight about where that comes from.
The figure goes back to the 1920s. Whiskey historian Fred Minnick, writing in Bourbon+, puts it as something the government feared. Another account credits it to a woman Prohibition agent who thought women might be selling five times as much liquor as men. Neither version comes with a name, a date or a method. It was a guess made by people who were alarmed, at a time when newspapers loved a lady bootlegger story.
It can't be checked now, because most bootleggers of either sex were never arrested and women were arrested less readily than men. What the surviving records do show is that women were everywhere in the trade and that the authorities at the time believed they were losing to them. That's a strong enough claim without the multiplier.
The search problem
The single biggest advantage women had was that men weren't supposed to touch them. Several states had laws stopping male officers from frisking or searching female suspects, as the Library of Congress's law blog notes, and where there was no law there was still custom.
Accusing a respectable woman of carrying liquor was thought insulting. Putting your hands on her to find out was unthinkable.
Women used this without mercy. In November 1925 Montana's only woman prosecutor, Emily Stone, sat in a meeting with the state attorney general where officials complained about women who carried bottles inside their blouses, knowing no officer would look there.
An Ohio dry agent told the Hamilton Evening Journal in 1924 about a woman in a raided bar who simply stood up, laughed at him and promised to sue anyone who laid a finger on her.
Fashion helped. The loose skirts, fur coats and garters of the 1920s could hide a surprising amount, and the garter flask became a fad in its own right. In Denver, an officer stopped a woman carrying what looked like a baby and found a gallon of whiskey in the blanket, which closed a six-month investigation.
Organised gangs caught on quickly. This was the decade of Al Capone and his old boss Frankie Yale, and the syndicates hired women to ride along in liquor cars because a woman in the passenger seat was cheap insurance. One of them, Edna Giard, ran liquor for Capone between Chicago and the upper Midwest. The Boston Daily Globe observed that no self-respecting federal agent liked to hold up a car with women in it. It was the same trick London's Forty Elephants had been pulling in department stores for decades: if nobody expects a woman to be a criminal, she can walk straight past them.
The women sent to catch them
The obvious answer was to hire women. In March 1920 Denver appointed Edith Barker as its first fully accredited policewoman, and History Colorado's account of her career says the Women's Christian Temperance Union paid her salary for the first two years because the state wouldn't. She was trained in jiu-jitsu and with a revolver, became one of the best shots on the squad and went on raids specifically to deal with the women. It was Barker who found the whiskey baby.
At federal level, Georgia Hopley became the first woman Prohibition agent in 1922. She argued that women lawbreakers used more tricks than men and that it took a woman to spot them. The most famous was Daisy Simpson of San Francisco, the “Lady Hooch Hunter”, whose story is told by the US National Archives. She worked undercover in five cities and was known for her disguises, though judges complained that many of her cases were trivial or looked like entrapment. In 1925 her office barred women from field work. She resigned rather than become a stenographer, and within a year she'd been arrested on drugs charges in Texas.
They were always a handful among thousands of men, most of whom looked more like Richard ‘Two Gun’ Hart, Al Capone's lawman brother. But the person in charge of prosecutions was a woman, and the highest-ranking one in the federal government. Mabel Walker Willebrandt was Assistant Attorney General for eight years, prosecuted thousands of Prohibition cases and won the Supreme Court argument that illegal income was taxable, which is the weapon that eventually put Capone away. The National Archives' profile of her adds two details worth knowing. She didn't personally support Prohibition. And in 1927 she got Congress to open the first federal prison for women, at Alderson in West Virginia, partly because the courts were suddenly producing so many women prisoners.
Leniency, and where it ran out
Judges didn't like jailing mothers. Minnick's research turned up a run of cases that show how little risk there often was. A Milwaukee woman admitted in 1925 that she'd been making $30,000 a year. She was fined $200 and given a month. In Denver, 22-year-old Esther Matson was sentenced in 1930 to go to church every Sunday for two years. President Warren Harding pardoned a Michigan woman bootlegger, and Ohio's governor cut another woman's sentence to five days.
Montana courts were no tougher. Lavinia Gilman, the 80-year-old with the 300-gallon still, got a warning because the judge assumed the equipment was really her son's. Colorado had Catherine Mucks, caught with a flask of whiskey at a dance. She pointed out that there was a cockroach in it, so it couldn't be a beverage fit to drink, and the judge let her go.
Not everyone thought this was right. When two women were caught hauling whiskey near Creede, Colorado, in 1918, dressed in men's suits, the local paper was asked to leave their sex out of the report and refused, on the grounds that “Sex should make little difference”.
And the leniency had limits, especially for repeat offenders and especially once the Depression arrived. In May 1932 Mary Toia, a 36-year-old mother of six, stood in front of a federal judge in New Orleans on her third arrest. The New-York Historical Society's Women & the American Story project reproduces the Times-Picayune report. She took all the blame so that her husband could stay home with the children, telling the court, “My husband had nothing to do with the liquor.” She got a year and a day at Alderson and a $300 fine.
Moonshine Mary and the drink that killed
The worst outcomes came when the product was bad. Home distilling was dangerous at both ends. Stills exploded, and liquor made carelessly, or cut with industrial alcohol, could blind or kill whoever drank it. Readers of our piece on Ruth Snyder will remember her husband pouring away a bottle of poisoned whiskey and blaming his bootlegger. It was a believable thing to blame.
In late 1923 a man called George Rheaton died after drinking at a house in the western suburbs of Chicago where a 34-year-old Polish immigrant, Mary Wazeniak, sold shots at 15 cents each. Her moonshine contained methanol. One account of the case describes her as a widow with three children, and others say she was supporting a dying husband. Either way she became the first woman in Illinois convicted over a death from moonshine, and she was sent to Joliet for one year to life. The papers called her Moonshine Mary. What happened to her afterwards isn't recorded.
Bertie Brown, who made the best in the country
Bertie Brown, sometimes written Birdie, was a Black woman from Missouri who arrived in central Montana in about 1898, when she was in her twenties. The historian Ellen Baumler has pieced her life together. Brown filed a homestead claim on Brickyard Creek in Fergus County in 1907 and proved it up in 1912, which made her one of the first Black women to homestead alone in the state. She kept leghorn chickens and a garden, grew wheat, oats and barley on 25 acres and lived with a cat.
In the 1920s she added a still. Her home brew was said locally to be the best in the country and her parlour turned into the place to go. Anyone who wanted a party out of sight of the revenue men knew to point the car towards Black Butte.
It ended in May 1933, months before repeal. Brown also took in dry cleaning, which in those days meant washing clothes in gasoline. She was doing a load while tending what she'd reportedly been told had to be her last batch of moonshine, and the fumes went up in her face. She died of her burns a few hours later.
Her name is on a bottle now. A Texas company, Saint Liberty Whiskey, sells a bourbon called Bertie's Bear Gulch in her honour.
Josephine Doody, the Bootleg Lady of Glacier Park
Josephine Doody's story sounds invented, and bits of it may be. The outline that Montana historians accept goes like this. She was born in Georgia, worked as a dance-hall girl and left Colorado in a hurry after a man was shot dead. She fetched up in McCarthyville, a rough railway camp near Marias Pass, with an opium habit.
A Glacier Park ranger called Dan Doody saw her dance there and decided to save her, which he did by carrying her off on a mule to his cabin on the Middle Fork of the Flathead River and keeping her there until she was clean. She stayed, and as Josephine Doody she became a formidable backwoodswoman, hunting, fishing and guiding.
Dan died in 1919. Josephine kept the homestead and went into moonshine, and her customers were the crews of the Great Northern Railway. The trains would stop at Doody siding and sound the whistle, one blast for each measure of whiskey wanted, and she'd row the order across the river. She died of pneumonia in 1936, in her eighties. Her grave was unmarked until 2009, when local history enthusiasts gave her a headstone with the nickname on it.
Willie Carter Sharpe and Maggie Bailey: the mountain trade
In the Appalachians, moonshine was an industry long before Prohibition and stayed one long after. Franklin County, Virginia, called itself the moonshine capital of the world, and its best-known driver was a woman. Willie Carter Sharpe grew up in neighbouring Floyd County, went to Roanoke at 17 to work in the mills and married the son of a big local moonshiner. Blue Ridge Tales has her organising convoys of up to ten cars out of a Franklin County filling station, running whiskey to Roanoke and on to Lynchburg, Washington and Baltimore.
Estimates of what she moved between the early 1920s and 1931 run from 145,000 to 250,000 gallons. She was stopped 13 times for speeding and reckless driving before she was finally arrested for the liquor in May 1931 and sent to Alderson for three years. Her trademark was a set of diamonds fixed in her teeth.
She came back into the news in 1935 as a witness at the Franklin County conspiracy trial, which the Blue Ridge Institute describes as the longest in Virginia's history up to then, with 34 defendants including nine government officials. The novelist Sherwood Anderson covered the story for Liberty magazine. The exhibit remembers her as the queen of the Roanoke rum runners. She turned up to testify dressed all in white and, for once, without the diamonds.
Maggie Bailey of Harlan County, Kentucky, lasted rather longer. She started selling moonshine at 17 and was still selling liquor from her house in Clovertown in her nineties. NPR marked her death in December 2005, at 101, under the title she'd carried for decades: Queen of the Mountain Bootleggers.
Her Lexington Herald-Leader obituary says she was charged at least 100 times and almost never convicted, including six acquittals in a single day, because Harlan County juries wouldn't do it. She paid for coal and groceries for poor neighbours and put several local youngsters through college. The one stretch she did serve was two years at Alderson, from 1941 to 1943, over 150 half-gallons of moonshine. Her former lawyer Otis Doan, by then a judge, said of her: “In all the years I represented her, she never lied to me.”
Gertrude Lythgoe, Queen of the Bahamas
At the other end of the scale was Gertrude Lythgoe, known as Cleo, who never went near a still. When Prohibition began she was a stenographer for a British liquor exporter in New York. She moved to Nassau in the Bahamas, where liquor was perfectly legal, and set up as a wholesaler selling Scotch to anyone who cared to sail it north. Saveur's profile of the women rum runners says she was the only woman to hold a full wholesale liquor licence there.
Nassau in the early 1920s was a boom town full of hard men, and Lythgoe had to convince them she wasn't to be cheated. One story has her threatening to shoot a man who'd been running down the quality of her whisky. Her best customer was Bill McCoy, the original Real McCoy, who trusted her stock because, like his, it wasn't watered. In time she stopped just supplying other people's boats and commissioned her own.
That made her a target. Minnick records that she was strip-searched by a woman officer at a US port, one of the few times the authorities found a way round the search problem. It also made her famous. Papers from Jamaica to New York ran her photograph and men wrote in offering marriage. The Wall Street Journal guessed her fortune at more than a million dollars. That's about as firm as the number gets, because she never discussed money.
She was arrested in New Orleans in the mid-1920s and, as Mental Floss's account has it, walked away without a prison sentence. She took it as a sign and got out while she was ahead, saying afterwards, “I just beat my jinx before it got me.” She spent the next half century living in hotels and died in Los Angeles at 86. Flags in Nassau were flown at half-mast.
Spanish Marie, Bessie Starkman and the title nobody would claim
Lythgoe had rivals, and the same Mental Floss round-up covers one of them. Marie Waite, called Spanish Marie, took over her husband's Florida rum-running business after he was killed and built it into a fleet of radio-equipped speedboats working between Havana and the Keys, with instructions broadcast in Spanish to confuse the Coast Guard. When her flagship was caught in 1928 with hundreds of casks of rum aboard, she paid a $3,000 fine and carried on. After repeal she reinvented herself as a car mechanic.
Across the border, a great deal of the liquor heading south passed through the hands of Bessie Starkman in Hamilton, Ontario. The Canadian Encyclopedia calls her the driving force behind the gang fronted by her partner Rocco Perri. She placed the orders, ran the payroll, laundered the money and negotiated with other gangs. On 13 August 1930 two men with shotguns killed her in her own garage. More than 20,000 people turned out for the funeral and nobody was ever charged.
The press wanted a single Queen of the Bootleggers and kept trying the crown on different heads. Minnick tells the story of Mary White, arrested by federal agents in 1921 with $5,000 in cash on her. A reporter asked if she was the Queen. Her reply deserves to be better known: “I wish the hell I was.”
Mary Dowling, who took her distillery to Mexico
Not every woman in the trade started out illegal. Mary Dowling had run the Waterfill and Frazier distillery in Kentucky for years after her husband's death, which was unusual enough. When Prohibition shut her down she applied for one of the licences to make medicinal whiskey and was turned down. So she sold her stock to bootleggers and obliging doctors instead, and hid the rest under the floorboards.
Two bootleggers turned informant set her up. Agents seized nearly 500 cases worth about $50,000, Dowling and her daughters were fined and two of her sons got a year each. Her answer, in Mental Floss's telling, was to take the distillery apart and rebuild it across the border in Juárez, with help from Joe Beam of the bourbon family, and sell perfectly legal whiskey from Mexico. She died in 1930, three years before she could have brought it home.
Aunt Vivian's bedtime stories
The strangest career belongs to Elise Olmstead of Seattle. She was English, and in the early 1920s federal agents recruited her to get close to Roy Olmstead, a former police lieutenant who'd become the biggest liquor smuggler on Puget Sound. She got close, fell for him and married him in August 1924. When the agents wanted her evidence, she declined to give it.
The couple then went into radio. HistoryLink records that they built a station, KFQX, in a spare bedroom of their mansion, and Elise went on air as Aunt Vivian, reading bedtime stories to the children of Seattle. Prohibition agents became convinced the stories were coded instructions to Roy's boats.
They probably weren't. Researcher Rebecca Demarest told KUOW that the Olmsteads' daughter thought any signals would have been slipped into the race results or the news. But the couple enjoyed the rumour too much to deny it: “they loved the idea of a bunch of prohibition agents sitting around a radio”.
Agents raided the house in November 1924. At the trial Elise was the only woman among dozens of defendants, played the unassuming housewife and was acquitted. Roy was convicted on wiretap evidence, and his appeal became Olmstead v. United States, the Supreme Court case that first tested whether the government could tap a phone without a warrant. Elise spent years campaigning for his pardon, got it and then divorced him.
Texas Guinan and the women at the bar
Before Prohibition, American saloons were for men. Some had a ladies' entrance and a side room. Colorado went further and in 1901 made it illegal for a woman to set foot in one. A woman seen drinking in public was assumed to be no better than she ought to be.
Speakeasies changed that almost by accident. Once the whole place was illegal, nobody was going to enforce the old rules about who could stand at the bar. Men and women drank and danced together, restaurants began offering table service for women who didn't fancy a bar stool, and a generation of young women treated a flask in the handbag as normal. This is the world of the cocktail books of the period, and of chancers like Rebecca Bradley, the Texas ‘flapper bandit’.
Its ringmaster was Mary Louise Cecilia Guinan, born in Waco in 1884 and known to everyone as Texas. She'd been a vaudeville cowgirl and made a string of silent westerns before the bootlegger Larry Fay installed her as hostess of his El Fay Club in 1924. Britannica credits her with single-handedly creating an atmosphere no other club could match. She greeted customers with “Hello, sucker!” and they loved her for it. She was arrested again and again and never convicted, because nobody could prove she owned the clubs. She died in Vancouver in November 1933, a month before Prohibition did.
It wasn't only an American pattern. In Sydney, where the pubs shut at six, Kate Leigh built a criminal empire on after-hours sly grog in exactly the same years.
The women who made Prohibition, and the women who ended it
The irony in all this is that Prohibition was, more than any other American law, something women had campaigned for. The Women's Christian Temperance Union saw drink as the thing that emptied pay packets and put wives in hospital, and it was superbly organised. It drove Montana's state ban through a referendum in 1916 and was credited with getting Colorado's enforcement law onto the statute book. The women who'd fought for the vote and the women who'd fought the saloon were very often the same women.
It wasn't only white women. The National Museum of African American History and Culture points out that temperance had deep roots in Black politics, running from Frederick Douglass and Sojourner Truth to Ida B. Wells and W.E.B. Du Bois. Douglass saw drink as a tool slaveholders had used to keep people down. The poet Frances Ellen Watkins Harper ran the WCTU's national department for work among Black women. It was a qualified welcome. From the 1880s the union let its branches segregate and Harper's department was rarely given enough money.
By the late 1920s plenty of them had changed their minds. The law hadn't produced sobriety. It had produced gangsters, corrupt policemen and teenagers drinking in unlicensed dives. In 1929 Pauline Sabin, a New York socialite who'd sat on the Republican National Committee, founded the Women's Organization for National Prohibition Reform. The Gotham Center's history of repeal says it grew to 1.5 million members, about three times the size of the WCTU, and it destroyed the idea that American women spoke with one voice on drink. Looking back, Sabin allowed herself a little pride: “I do think our little organization did something to perfect this wet landslide”.
The 21st Amendment was ratified on 5 December 1933. The Colorado Encyclopedia records Denver papers reporting women in public “Drinking Beer Openly and With Gusto”.
What happened to the kitchen stills
For the women who'd been making a living from it, repeal was a redundancy notice. Legal beer and whiskey came back and the market for home-made liquor vanished overnight. The rum queens retired or found other work. The mothers of Butte and New Orleans went back to taking in washing and lodgers, in the worst years of the Depression, without the income that had been keeping the family fed.
A few never stopped. And the drinking the decade had normalised didn't stop either. Alcoholics Anonymous was founded two years after repeal.
What's left of them is mostly scraps: a line in a court ledger, a newspaper paragraph written for laughs, a daughter's memory of the price of a pint. That's the real reason the gangsters got the films. They left better paperwork.
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Sources
Montana Women's History, Montana's Whiskey Women: Female Bootleggers during Prohibition
Ellen Baumler, Two Legendary African American Homesteaders, Montana Women's History
Distinctly Montana, Nuts to the Noble Experiment: Montana's Cussed Women Bootleggers
JSTOR Daily, Whiskey, Women, and Work (on the research of Tanya Marie Sanchez and Mary Murphy)
New-York Historical Society, Women & the American Story, A Bootlegging Mother
Fred Minnick, How Women Bootleggers Dominated Prohibition, Bourbon+
Alcohol Problems and Solutions, Women Bootleggers and Women Prohibition Agents
History Colorado, Openly and with Gusto: How Women Moonshiners Led to Denver's First Female Cop
US National Archives, First Lady of Law: Mabel Walker Willebrandt
Saveur, Meet the Swashbuckling Female Rumrunners who Ran Prohibition
The Whiskey Wash, New American Whiskey Inspired By Historic Montana Female Bootlegger
National Museum of African American History and Culture, Black Prohibition and Temperance
Center for Women's History and Leadership, Frances Harper and Black Women in the WCTU
Blue Ridge Tales, Willie Carter Sharpe: The Rum-Running Queen of Virginia
