Buzz
On New Year’s Eve 1919, people nationwide celebrated what they thought would be their final night of legal drinking before the Volstead Act took effect on January 17, 1920. Little did they know, this marked the beginning of a transformative era that would defy expectations.
While some anticipated that banning alcohol would lead to a healthier society fueled by soda and gum, others seized the chance to profit. Legendary figures like Al Capone, Lucky Luciano, and Bugs Moran became infamous in the bootlegging world. By 1930, the illegal liquor trade had grown into a billion-dollar industry, drawing in more than just ordinary criminals.
Contrary to the belief that female bootleggers were rare, historical records reveal their significant presence. Mary Sullivan, head of the New York Women’s Police Department, claimed in 1926 that women were unfit for such roles. Yet, evidence suggests that women outnumbered men in bootlegging, with an estimated ratio of five to one. Their layered clothing helped conceal alcohol, and laws preventing male officers from searching them gave them an edge.
Countless captivating stories of bold women who entered the illicit liquor trade have been lost to history, but a few remarkable tales endure.
1. Gertrude “Cleo” Lythgoe
Known as “Cleo” after the iconic queen Cleopatra, Gertrude Lythgoe was a sharp, fashionable, and towering figure who carried a pistol. A chain smoker with a passion for singing, she had numerous romantic pursuits but refused to marry. “I’ve always been independent, and I regret nothing. I answer to no one, and I’ll never let a husband control me,” she once said.
Starting as a stenographer, Lythgoe soon landed a lucrative role with a whisky distributor operating in Britain and New York. When the Volstead Act disrupted the industry, she relocated to the Bahamas, aiming to oversee Scotch whisky imports to the islands and then smuggle it into the U.S.
Residing at the Lucerne Hotel, a notorious hub for bootleggers, she entered the perilous, male-dominated trade. She allied with famed rum smuggler Bill McCoy, utilizing his ships to move her liquor from the Bahamas to Rum Row, a zone off the U.S. coast where contraband-laden ships waited for smaller boats to ferry the goods ashore. Eventually, Lythgoe established her own fleet, earning respect for her trustworthy operations and premium Scotch.
From 1920 to 1925, she earned millions by smuggling liquor into major port cities such as New York. Her success turned her into an unexpected celebrity, frequently landing her on the front pages of newspapers.
After surviving a shipwreck, Lythgoe was arrested and faced trial in New Orleans. While she escaped imprisonment, she became convinced she was cursed and feared for her safety. At the peak of her career in 1925, she suddenly left the rum-running business. “I’m done for good. I escaped my curse just in time. It was terrifying to see it closing in,” she later told the press. She spent her remaining years living in various hotels.
2. Mary Louise Cecilia “Texas” Guinan
Mary Louise Cecilia Guinan thrived in the spotlight. After marrying young, she moved from Texas to Chicago with her cartoonist husband. However, Guinan despised domestic life and aspired to be a performer. In 1906, she left her husband and headed to New York City to chase her dreams on the stage.
Initially struggling in a city teeming with aspiring stars, she eventually broke into Vaudeville as a bold, gun-toting cowgirl named “Texas” Guinan. Her unconventional persona and striking appearance caught attention, propelling her to fame in silent films. However, as the 1920s began, Guinan, nearing her forties, faced the harsh realities of ageism in her industry.
The lively star reinvented herself as a charismatic host in New York’s booming speakeasy scene, fueled by anti-Prohibition sentiment. Hired by prominent bootlegger Larry Fay, who owned the El Fey nightclub, she energized crowds to keep them drinking longer. Later, Guinan went independent, founding multiple clubs across the city and earning the title “Queen of the Nightclubs.” While speakeasies and dingy bars known as “blind pigs” were everywhere, few could match the allure of the venues she ran.
Guinan became famous for entertaining intoxicated crowds with humor, teasing, skits, and group songs. Her signature greeting, “Hello, Sucker,” became iconic. Her clubs attracted stars like Babe Ruth and Charlie Chaplin, and it’s rumored that she often entertained the exiled King Edward VIII, who once disguised himself as a kitchen worker during a police raid.
As the Prohibition era ended, Guinan briefly returned to stage acting before her sudden death in 1933 in Vancouver, Canada. Her funeral in New York drew thousands, with mourners scrambling for flowers and even clashing to catch a glimpse of her coffin.
3. Besha “Bessie” Starkman-Perri
Besha “Bessie” Starkman began with a modest life. A seamstress turned homemaker, she raised two daughters in Toronto’s infamous St. John’s Ward slum. Known for her sharp tongue, numerical skills, and ambition, she took in boarders to supplement her husband’s income as a bakery driver. However, she yearned for more and sought to transform her life entirely.
When Rocco Perri, a charismatic Calabrian man, rented a room with the family, his charm and grand ambitions captivated her. The pair relocated to a city near the U.S. border, where they built a bootlegging empire that rivaled even Al Capone’s.
Starting small, Starkman ran a brothel from their home while Perri sold modest quantities of illegal liquor. They also ventured into racetrack betting. Over time, their operations expanded, and they earned over $1 million annually—equivalent to more than $13 million today.
Despite repeated police interventions and violations of Canada’s Temperance Act (akin to the U.S. Volstead Act), the couple cleverly continued their illicit activities. Perri charmed suppliers and clients across the border, while Starkman managed the finances and strategy, serving as the mastermind behind the scenes. Publicly, she portrayed herself as a dutiful wife, but her cunning days were limited.
In August 1930, Starkman was shot dead in an ambush as she returned home. With nearly $10,000 in jewelry still on her body, robbery was ruled out as a motive. Thousands gathered at her funeral in Hamilton, Ontario, to honor one of Prohibition’s most successful female bootleggers. Her murder remains unsolved.
4. “Moonshine Mary” Wazeniak
Desperate to maintain their income and satisfy customers, some amateur moonshiners resorted to a risky shortcut: methanol. They reprocessed the toxic wood alcohol to reduce its lethality, masking its foul taste with sugar and dyes. This dangerous concoction was sold as whisky, rum, and more. However, improper distillation could lead to nerve damage, blindness, or even death.
This tragic outcome befell George Rheautan, who died suddenly after drinking at a bar one November night in 1923. After buying cheap shots at a blind pig, he collapsed and died nearby. Soon, Mary Wazeniak, the bar’s owner, found herself in legal trouble.
Dubbed “Moonshine Mary” by the press, Wazeniak was portrayed as a Polish working-class mother operating a popular speakeasy from her Brookfield, Illinois, home. She testified that her business was her only means to support her ailing husband and three children, but the courts showed no mercy.
To set an example, she was sentenced to one year to life for manslaughter, marking the first moonshine-related conviction in Illinois history. Wazeniak was tearfully led to Joliet prison in shackles. Her fate afterward remains a mystery.
5. “Spanish Marie” Waite
Marie Waite and her husband, Charlie, were a formidable duo in the rum-running business, managing a fleet of speedy vessels that transported liquor between Havana, Miami, and the Florida Keys. They enjoyed a luxurious lifestyle, owned multiple properties, and mingled with affluent clients eager to purchase premium Cuban rum.
Their glamorous life together didn’t last long. In April 1927, Charlie encountered trouble with the U.S. Coast Guard, which apprehended him and his crew unloading 300 cases of illegal liquor. Charlie was killed in the resulting shootout.
Despite her grief, Waite refused to let anyone take over her rum empire. Her resolve never wavered—she had two children to support. She continued her profitable operations between Cuba and Florida, overseeing up to 15 schooners and a skilled crew. She constantly devised new strategies to outmaneuver the Coast Guard.
Her team relied on an offshore radio to monitor Coast Guard movements and communicated in Spanish to evade detection. Known as “Spanish Marie,” she became an unstoppable force in the industry.
Although caught multiple times for smuggling large quantities of rum, Waite always escaped with minimal consequences, often paying fines. One notable incident occurred in 1928 when her flagship, Kid Boots, was seized with over 500 casks of rum onboard.
While rumors suggest Waite avoided trial and disappeared with her boat and fortune, the reality was different. She paid her $3000 fine and continued rum-running for years, facing new legal troubles, marriages, aliases, and adventures. After Prohibition, Waite broke barriers again, becoming Florida’s first female auto mechanic. As she famously said, “Women can do any job a man can.”
6. Mary Dowling
After her husband’s passing, Mary Dowling took charge of one of America’s most renowned bourbon producers, the Waterfill and Frazier Distilling Company. It was an unprecedented role for a woman, but she embraced the challenge. Dowling managed the distillery for years until Prohibition disrupted her operations.
Determined to save her legacy, Dowling searched for a loophole. While the 18th Amendment banned most alcohol, medicinal use was allowed. Predictably, alcohol prescriptions for ailments like asthma and diabetes surged nationwide. Dowling’s request for a medical whiskey license was rejected, forcing her to shut down her distilleries.
Unwilling to waste 3500 gallons of top-quality bourbon, she sold much of it to bootleggers, dubious doctors, and underground buyers. She hid the rest beneath her house’s floorboards and basement. Her stash remained concealed until two informants tricked her into selling bourbon. Authorities raided her home, seizing nearly 500 cases of whiskey worth $50,000 and accusing Dowling and her children of violating Prohibition laws.
For years, Dowling adamantly insisted her family had broken no laws, arguing the alcohol was for personal use, not sale. She fought to have the charges dismissed and demanded the return of her whiskey, but her efforts were in vain. The court found the family guilty; Dowling and her daughters faced hefty fines, while her sons were sentenced to a year in prison.
Despite the setback, Dowling persisted in keeping her business afloat and outwitting the authorities. With the assistance of Joe and Harry Beam (of the Beam whiskey dynasty), she relocated her distillery to Juarez, Mexico, to bypass U.S. Prohibition laws. Dowling and her sons rebranded as Dowling Mexican Distillery, continuing whiskey production south of the border.
The Dowlings successfully expanded their market to Central and South America, capitalizing on tourists and bootleggers crossing the Rio Grande. Their bourbon’s popularity overshadowed many legal medicinal distilleries. Though Dowling passed away in 1930—before Prohibition’s end—her children carried on the family legacy, eventually resuming production in the U.S.
7. Elise Olmstead
Born in England, Elise Caroline Parché (sometimes referred to as Campbell) worked for British Intelligence during World War I before moving to Canada in 1919. She later settled in Seattle, Washington, where she opened a beauty salon under the alias Vivien Potter.
Her adventurous spirit led her to become a dry-agent spy for the Bureau of Investigation. Assigned to gather intelligence on Roy Olmstead, a former police officer turned rum runner, she infiltrated his operation as a bookkeeper. Over time, the unexpected occurred: Elise and Roy fell in love and married. When authorities demanded she testify against him, she famously declared, “I cannot testify against him; I am his wife.”
The couple settled in a lavish home in Mount Baker, enjoying the wealth from Roy’s rum-running empire. Roy enlisted inventor Alfred Hubbard to create a powerful radio station, operated from their spare bedroom. Elise became the soothing voice of “Aunt Vivien,” reading bedtime stories to children each night.
However, something seemed off. Her stories often included odd phrases like big bear, run for cover, which didn’t fit the narratives. Suspecting Elise was sending coded messages to rum runners, Prohibition agents recruited Hubbard as an informant and began wiretapping the station.
Three months later, federal agents raided the Olmsteads’ home during one of Elise’s broadcasts. Listeners heard a commotion before the show went silent. Roy was convicted of leading the largest liquor smuggling operation of the era and served four years in prison. Elise, however, was unexpectedly acquitted.
8. Gloria De Caseras
Madame Gloria De Caseras, famously dubbed the “beautiful bootlegger,” was a figure of fascination across the Atlantic. She reportedly commanded a fleet of whisky ships that frequently traveled between Britain, Halifax, and Rum Row.
Gloria, separated from the son of an Argentine business magnate, had mysterious origins. Some believe she was Mabel Davy from East London, the daughter of a renowned sea captain. Others claimed she was Gloria De Veres, a British actress whose affluent father allegedly funded the Russian Bolshevik uprising before his mysterious death in Japan. Regardless of her past, Gloria consistently made news wherever she appeared.
During a voyage from Europe to North America, her five-masted schooner, General Serrett, encountered mechanical issues. She docked unexpectedly in England, prompting an inspection by British authorities, who discovered 10,000 cases of Scotch whisky, likely destined for America. When questioned about the ship’s ownership, the crew pointed to De Caseras, head of the Gloria Steamship Company. De Caseras vehemently denied involvement, insisting the cargo wasn’t hers.
While stranded in London, De Caseras made headlines again—this time for allegedly stealing a dress from Selfridges, a luxury department store. Though it was later deemed a misunderstanding over an inactive credit account, the incident became a media sensation.
To settle her debts, De Caseras sold her ship and didn’t return to the UK until 1927. She expressed a desire to return to her homeland permanently but was shocked to find unpaid fees from her earlier troubles. Having renounced her British citizenship after marrying her Argentine ex-husband, she was denied the right to remain in the country.
With only £5 worth of clothing left after her belongings were confiscated, De Caseras was closely monitored in a luxury hotel room until her deportation. She traveled to Halifax, but Canada also rejected her, deeming her too risky. As the self-proclaimed “Queen without a home” stated, “I am a woman seemingly without a country, even though I was born in England.”
De Caseras faced the same reception in New York, where she was given 15 days to leave. She headed inland and disappeared. Later, reports surfaced about her plans to marry Albert Charboneau, an American business partner involved in rum-running ventures.
