Gertrude “Cleo” Lythgoe: The Bootlegger Queen

While prohibition-era whiskey smuggling is populated by male figures, women also had a hand in ensuring America never went dry. The most infamous of women rumrunners was Gertrude “Cleo” Lythgoe known as the “Queen of the Bootleggers”. Between 1920 and 1926 Lythgoe ran a very successful liquor wholesale and rumrunning business out of Nassau, Bahamas, providing American markets with premium Scotch and American Whiskey. She was known equally for her business skills as for her looks; she earned the nickname “Cleo” after Cleopatra and gained quite a popular following in the press, receiving countless fan letters and marriage proposals.

Born in Bowling Green, Ohio, Lythgoe got a rather unremarkable start in the rumrunning business. She had been a stenographer in San Francisco before losing a lot of money in the stock market and looking for a new start. She began working for a London based liquor exporter and quickly realized the opportunity that Prohibition provided. Whoever could get premium liquor to the American market had the potential to make it big, and the Bahamas were the perfect home base. So Lythgoe set up shop in Nassau, Bahamas, importing wholesale premium Scotch and American Whiskey.

Lythgoe was the first women to own a wholesale liquor license in the Bahamas and she faced her fair share of difficulties because of her gender. At the time, some men would not do business with her because she was a women and she was not allowed in certain bars and clubs. However, whatever reticence certain men had was quickly overcome when they saw the quality of her products and her skill in business. It is debated who exactly Lythgoe worked for — was she an American spy? Was she working for a British distributor? — but Bill McCoy believes she was an agent for Haig’s and McTavish’s Scotch Whiskey. If McCoy is right, Lythgoe provided American markets with two of the best Scotch brands of the time. In either case, the quality of the products she offered was undisputed and she even went as far as threatening to shoot a man who defamed her liquor.

As far as the rumrunning went, Lythgoe’s business model was genius. She would import liquor to the Bahamas and then sail to just off the coast of America, looking for ships that were willing to buy her product and transport it to land. She had to be constantly on guard for both hijackers who made their living stealing illegal liquor and reselling it and the Coast Guard who would not hesitate to arrest her. But as long as Lythgoe never entered American waters she was technically not doing anything illegal. Selling alcohol in American jurisdiction was illegal, but American jurisdiction does not apply to international waters. The conditions of her wholesale license prohibited her from selling liquor in other jurisdictions, but international waters were the magic loophole. As long as she stayed out of American waters she could not be arrested by American authorities or found in contravention of her Bahamian wholesale liquor licence.

During this time Lythgoe also worked with renowned rumrunner Bill McCoy. She used her connections as a wholesaler to import premium Scotch, rye, and bourbon, and McCoy provided help on the logistics end. She often sailed with him to the coast to sell her liquor also carrying a pistol, just incase.

However, all good things come to an end, and Lythgoe’s rumrunning business is no exception. Two things contributed to her eventually giving up the business. First, the US government extended its jurisdiction on coastal waters from 3 miles to 12 miles. This made rumrunning incredibly difficult as ships needed to stay four times farther away from the coast to sell their wares. This might not have been enough to convince Lythgoe to give up the business by itself, but it unfortunately coincided with some legal troubles. Lythgoe was mistakenly arrested in Miami, but before she was released, the officers realized who they had caught and alerted federal authorities. She was then brought to New Orleans and charged with smuggling 1’000 cases of whiskey. Always one step ahead, Lythgoe turned the charge on its head, thanking the federal authorities for finding her whiskey, claiming she was not smuggling it but that it had been stolen. Whether the federal authorities believed her or not we will never know, but Lythgoe was allowed to become a state’s witness and testify against other smugglers, freeing her of all charges.

After this brush with the law Lythgoe formally retired from the liquor wholesale and rumrunning business, retreating into relative obscurity and privacy. She published her autobiography The Bahama Queen : The autobiography of Gertrude “Cleo” Lythgoe, prohibition’s darling beauty in 1964, but much of the details of her life remain hazy. We do know that she never married, however, despite receiving countless offers from men who witnessed her meteoric rise to fame in the 1920’s. In any case, Gertrude Lythgoe represents a strong example of women’s participation in prohibition era rumrunning.


Fred Minnick, Whiskey Women (2013).

Gertrude Lythgoe, The Bahama Queen : The autobiography of Gertrude “Cleo” Lythgoe, prohibition’s darling beauty (1964).

Mary Dowling and Waterfill and Frazier

Mary Dowling and Waterfill and Frazier

When prohibition hit America, many distillers went underground, hoping to