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Women, Guns and Whisky: Girls Gone Wild 1920’s Gangster Style

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Women were once considered by the police to be “incapable” of bootlegging illegal alcohol. They sure had everyone fooled. Beginning on January 17, 1920, possession and use of alcohol became as illegal as shooting heroin. The idea was to force America to stay sober but everyone knew that was never going to work. Today, everyone’s heard of Al Capone, Lucky Luciano and Bugs Moran but Gertrude Lythgoe and several just like her slipped right under the radar.

Women with alcohol and attitude

Women bootleggers were apparently more ruthless and opportunistic than their male counterparts. Several have been documented by historians who managed to ply their trade with considerable success, without going to prison. Gertrude Lythgoe didn’t like the name she was born with so preferred “Cleo,” after Egyptian Queen Cleopatra.

Described as “pistol-slinging,” Cleo was “tall, ever-so-stylish, and smart as a whip. She also smoked like a chimney and loved singing.” She enjoyed the company of men but wasn’t interested in marriage. “I’ve stood on my own feet, and I’m ashamed of nothing. I’m my own boss, and I’ll never take a husband to boss me,” she once declared.

The stenographer got word of a better opportunity and began working for “a whisky wholesaler out of Britain and New York.” When prohibition hit, “Lythgoe moved to the Bahamas, intending to lead Scotch whisky imports to the island nation before rerouting the liquid gold to America for illegal resale.” Cleo soon started rubbing elbows with smugglers like Bill McCoy, who “used his fleet to transport her liquor north from the Bahamas to Rum Row.

That was “a stretch of international waters off the U.S. coast where ships filled with contraband liquor bobbed at sea, awaiting small dispatch vessels to arrive and sneak the cargo to mainland America.” Sort of like with the cocaine trade today. She soon became one of the most successful women smugglers. “Between 1920 and 1925, she made millions moving liquor into port cities like New York. She was so successful she became an unlikely celebrity, often making front-page news.

After surviving a shipwreck, Lythgoe was arrested and hauled in front of a New Orleans judge. She beat the rap and decided to quit while she was ahead.

I’m out of it for good. I just beat my jinx before it got me. It was terrible to watch it coming.” Not all her smuggling sisters were that timid. Women have made big names for themselves in the industry.

Hated life as a housewife

The last thing Mary Louise Cecilia Guinan was going to be was a housewife. She loved the limelight and left her husband in 1906 to become an entertainer. She quickly adopted the character of a Texas cowgirl and became a hit on the Vaudeville circuit. After shooting to fame in silent movies, the 20’s roared in. She was in her 30’s and not about to become a tea-totaler.

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The vivacious star found new fame as an events host among the Big Apple’s growing anti-Prohibition speakeasies. She was hired by well-known bootlegger Larry Fay—who opened the El Fey nightclub—to hype up the crowd so they’d stay longer and buy more booze.” She was one of the women who caught on fast and soon “established several more clubs throughout the city, earning the moniker “Queen of the Nightclubs.” She had big name clients like Babe Ruth and Charlie Chaplin. “Rumors have it that she often hosted the abdicated King Edward VIII, who, in one instance, pretended to be kitchen staff during a police raid.

Besha “Bessie” Starkman was a seamstress-turned-housewife who “raised two young daughters in Toronto’s densely populated and notorious slum, St. John’s Ward.” Then opened a brothel with a Calabrian man named Rocco Perri. “The two took off to a neighboring city near the American border to start a life together. From there, they teamed up to create a bootlegging empire that would rival the likes of Al Capone.

Starting with an in-home brothel, “Perri provided small batches of illegal liquor to customers, and they both dabbled in racetrack betting. In time, however, business boomed, and they raked in over $1 million a year—more than $13 million today.” While women were meant to keep in the shadows, she played an innocent wife while being the brains of the operation. “Starkman was ambushed with a shotgun while returning home one August night in 1930. There was nearly $10,000 worth of jewelry left on her body, so robbery as a motive was out of the question.

Of all the women bootleggers Mary Dowling was the only one in the business of distilling alcohol before prohibition. “Upon her husband’s death, Mary Dowling took the helm of one of America’s largest and iconic bourbon manufacturers, the Waterfill and Frazier Distilling Company. It was a position unheard of for women, but she was up for the challenge. Dowling successfully ran the distillery for decades—until Prohibition threw her a wrench.” Attempting to remain on the good side of the law, she applied for permission to distill “medicinal” alcohol. She didn’t get it. “But she wasn’t about to toss away the 3500 gallons of premium bourbon in her warehouse. Instead, she sold off as much as possible to bootleggers, shady doctors, and numerous under-the-table clients. She stored what remained under the floorboards and in the basement of her house.

For some reason, the government wouldn’t buy her story that it was for the family’s personal consumption. “For several years, Dowling relentlessly claimed her family broke no laws because the booze was for personal consumption and not for sale. She pushed to have the charges dropped and demanded her whiskey be returned. But it was no use. The family was found guilty.” She paid her fine and moved the equipment to Mexico, with the help of Joe and Harry Beam. You may have heard of them.

What do you think?

Written by Mark Megahan

Mark Megahan is a resident of Morristown, Arizona and aficionado of the finer things in life.

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