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Women's History Month Spotlight: Women Bootleggers

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It's Women's History Month, and you'll read about all the usual bright women who helped change the world. Amelia Earhart, Hillary Clinton, Condoleezza Rice, yeah, yeah, we know about their accomplishments. What about the criminal-minded women who bootlegged whiskey, rum and gin during Prohibition?

You mean 1920s-era women were not all church-going sweet belles with bonnets and daisies?

In fact, the rowdy world celebrates the likes of Al Capone, George Remus and the "Real" Bill McCoy for their booze-smuggling prowess. But, women were far better bootleggers than men because many states had laws that made it illegal for male police officers to search women. Back then, it was considered insulting to accuse a woman of such a dastardly crime.

Women bootleggers would hide flasks, even cases, on their persons and taunt male police officers. "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," an unnamed Ohio "Dry Agent" told the Hamilton Evening Journal in 1924.

The alcohol smuggling syndicates took advantage of these legal loopholes, recruiting women into their ranks. Even if the gangs didn't hire women bootleggers, they hired them for ride alongs to reduce searches and robberies. "No self-respecting federal agent likes to hold up an automobile containing women," according to The Boston Daily Globe.

This had become such a problem for law enforcement officials that the government feared women bootleggers outnumbered men five to one. "On the Canadian, Mexican and Florida borders, inspectors are constantly on the lookout for women bootleggers who try to smuggle liquor into the States. Their detection and arrest is far more difficult than that of male lawbreakers," said Miss Georgia Hopley, the first female Revenue agent.

And frankly, bootlegging was good money with little punishment. In 1925, a Milwaukee woman admitted to earning $30,000 a year bootlegging. She was caught and fined $200 with a month's sentence to jail, netting $29,800 for the year. Denver's Esther Matson, 22, was sentenced to church every Sunday for two years after her bootlegging trial in 1930. Even President Warren G. Harding pardoned a Michigan woman bootlegger, and Ohio governor Vic Donahey commuted a woman's sentence to five days.

It seems as though the court system and politicians just didn't have the stomach for putting mothers and grandmothers behind bars. Most women were earning money just to keep a roof over their family's head and food on the table. But there were some pistol-packing ladies who commanded empires.

These profiteer bootlegging women had cool nicknames, such as the Henhouse Bootlegger, Esther Clark, who stored liquor in her Kansas chicken coop; Moonshine Mary, who was convicted of murder for killing a man with bad liquor; Texas Guinan, aka Queen of the Night Clubs; and my favorite, Queen of the Bootleggers.

Anytime a woman was arrested for bootlegging and enjoyed a nice living, the press hailed the woman as the Queen of the Bootleggers. In my research for Whiskey Women, I found a dozen women who were called Queen of the Bootleggers.

In 1921, federal authorities found $5,000 in bootlegging cash on Mary White, a stout woman with a "swarthy" complexion and missing front teeth. After sentencing, the press asked her if she was indeed the Queen of the Bootleggers, to which she replied: "I wish the hell I was."

Gloria de Casares, wife of a wealthy Argentinean merchant, reportedly commissioned whiskey ships that stocked up on Scotch and smuggled it back into the United States. In 1925, when her five-masted General Serret, was preparing to set sail for America from London, detectives seized her ship and found 10,000 cases of Scotch. Her captain ratted Gloria out, and neither she nor her ships could travel without harassment again. English authorities once confined her to a hotel room to make sure she wouldn't make any bootlegging deals. In the process, they confiscated her clothes. "What am I to do? First I am deprived of my nationality. Now they want to deprive me of all my clothes over $25 worth. Twenty-five dollars is just about enough for a hat. Do they expect a woman to go about the world with $25 worth of clothing," Casares told the New York Times.

Casares never admitted to bootlegging, but nonetheless she was a true worthy contender for the "Queen of the Bootleggers" title.

However, the greatest female bootlegger was Gertrude "Cleo" Lythgoe, a legitimate licensed liquor wholesaler in Nassau, Bahamas. A majestic-looking woman, Cleo was mistaken for Russian, French and Spanish, but she was American with ties to a British liquor distributor.

When Prohibition became law, she moved to the Bahamas and used her Scotland connections to import the best Scotch. In the Bahamas, this liquor was loaded on the boats of The Real Bill McCoy and brought into the U.S. liquor supply. But, Cleo eventually moved into commissioning her own boats -- that's where the money was, after all. Bootlegging also came with greater risk.

Like Casares, Cleo became a target of the U.S. authorities and was even stripped searched by a female officer at a port. But, unlike the other so-called Queen of the Bootleggers, Cleo loved the limelight and gave several media interviews. She became a true media darling with newspapers from Jamaica to New York publishing her photo. Men fell in love with her and sent "love letters" to the newspapers. An Englishman, who simply signed "One Who Loves You," wrote: "I only wish you lived in England. I would marry you, as a home life would be far more suitable for you than your present occupation."

But, Cleo said frequently "I don't need a man to tell me what to do." She was independent, strong and knew how to use her charm. She could also threaten a man quite well, staving off competition with razor blades and potential rapes with pistols.

When one of her boats was seized in 1925, Cleo turned state witness on her former employees, who "stole" her boat to run liquor into the United States. This trial quietly went away, and Cleo never bootlegged again.

The Wall Street Journal estimated she was worth more than $1 million, but nobody really knows. Cleo was cryptic and never incriminated herself about her illegal dealings.

That's the thing about women bootleggers. While the men were brash and loud, killing whoever got in their way, most women were swift and rarely talked.

It just goes to show: Women can keep secrets better than men. Until they get caught.