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Chicago History: The great adventure of Chicago May. “Queen of the Underworld”

During the first three decades of the 20th century, the Chicago newspapers, including the Tribune, couldn’t get enough of an Irish woman who became an international celebrity criminal on four continents.

She was nicknamed Chicago May. Her real name, which the papers never came across, was May Duignan.

It didn’t matter. Her reputation was a lot more interesting than mundane facts.

She was a woman who, the Tribune reported breathlessly, was the “Queen of the Underworld” and “the world’s cleverest woman crook” and “a pioneer in women’s rights in a world of crooks.”



The family’s entire savings

In her 2005 book “The Story of Chicago May,” biographer Nuala O’Faolain chronicled that May turned tricks and stole wallets in Cairo and Manhattan, was the hostess at a diplomatic ball in Rio de Janeiro, was rumored to have helped a boyfriend escape from Devil’s Island, and served nearly 15 years in French and English prisons.

She married a member of the Dalton Gang, Dal Churchill who, according to May, was lynched for trying to rob a train near Phoenix. She testified against novelist Stephen Crane, and she crossed paths with Countess Constance Markievicz, the Irish rebel.


May’s was a career that began early, on the day in 1890 when her mother gave birth to a fifth child in the family home in the small Irish town of Edenmore. That’s the night, O’Faolain wrote, that the 19-year-old May ran away — and took with her the family’s entire savings of 60 sovereigns, the equivalent of more than $5,000 in today’s money.

Soon, she was in Chicago for the World’s Columbian Exposition of 1893, but not as a tourist. She began working as a prostitute, con artist and thief among the close-packed brothels and saloons in the Levee, the Near South Side area now called Printers Row.


“Bit out the scarf pin”

It was during those early years, Tribune reporter Genevieve Forbes Herrick later asserted, that May became a groundbreaking scoundrel by “introducing the camera into the art of blackmail,” seducing a mark while a confederate took photographs.

She also “is credited with having perfected the fainting fit, during the agonies of which she would revive sufficiently to steal watches and scarf-pins of the men who were helping her.”

May apparently had a thing for scarf-pins. Herrick wrote of May’s “hansom cab trick” in which she would lure a man into a cab, letting him put his “arms about her trim waist, her blonde head on [his] shoulder.” In this cozy position, May was able to “bury her lips in his scarf and deftly to bit out the scarf-pin.”

In her feature story, published on January 15, 1928, Herrick wrote that, throughout her career, May was able to weave her magic with men because she was a “good-looking girl, with the baby stare, the fluffy hair, and the innocent eyes” as well as “a dreamy smile” and “enchanting eyes.”

Two photographs accompanied the story. One from earlier in May’s career showed her to be an attractive woman, but it was the second, taken at the time the story was written, that gave a better hint at her personality.


Pictured with a much younger British author whom she said she was going to marry, May exuded a nonchalant assurance and a “bubbling vitality” that were her trademarks, according to news stories. Her gaze was direct, and her mouth was set in a smirk of a smile. She told the Tribune she was 52. In fact, she was 57.



By this point, she’d had a long life with a lot of bumps in the road. Although Herrick wrote that May “made the front page of newspapers oftener than she made the desk sergeant’s entry book,” she’d spent a third of her life in prison.

A key man in May’s criminal life was Eddie Guerin, the scion of a well-to-do Chicago family who, upon his death in England in 1940, was described as an “incorrigible jail bird who had run the gamut of crime.”

In 1902, with May’s help, Guerin and an accomplice robbed the American Express office n Paris of $6,000, the equivalent of $165,000 today. When they were convicted in a French court, the Tribune reported, May “threw here arms around Guerin’s neck and kissed him.’

She was sentenced to five years in prison. Guerin was given life on Devil’s Island. Later, though, apparently with May’s help, he became one of the few prisoners to escape that infamous hellhole.

At the time of Herrick’s Tribune feature, May seemed to be attempting to turn over a new leaf. Later in 1928, she published a rough-hewn, straight-talking autobiography “Chicago May: Her Story — A Human Document by ‘THE QUEEN OF CROOKS.’ ”


Throughout her life, May used any number of aliases. For her autobiography, she called herself May Churchill Sharpe. Most news stories over the years referred to her as May Vivienne Churchill because of her short-lived marriage to Dal Churchill. She married a second time in 1927 to James Sharp of New Jersey. For the book, she added the “e” to Sharp perhaps to give her byline a touch of gentility.


“Her great adventure”

The years, though, were taking their toll on May.

In a 2005 interview, O’Faolain noted that May’s life had been far from cushy. She sold her body for money or as a lure for robbery. She engaged in scams that, when successful, netted great loot. But the money never lasted very long.

Even so, May lived a much more interesting life than she would have in Edenmore.

“May has some absolute core acceptance of herself,” O’Faolain said. “She never apologizes for anything. She’s perfectly open about what a bad, dreadful woman she was. She’s kind of matter-of-fact that life dealt her this hand of cards, and she played it her way.”

While the Tribune and other newspapers played up the glamor of May’s life as an international crook, it was a life without the benefits of a more mainstream existence, such as stability, membership in a family and roots in a community.

Still, O’Faolain said, “”This is not a negative story at all. The hope and vitality in this story takes longer to find than in conventional stories. You have to pay close attention to know that, in her terms, her life was a success — her great adventure.”


“Her bubbling vitality”

On May 24, 1929, just a year and a half from Herrick’s long feature on Chicago May, a woman who identified herself as May Vivienne Churchill checked into a Philadelphia hospital. She was there for an abdominal operation after which she was planning to marry, this time the prospective groom was a criminal acquaintance named Robert Considine, alias Charles Smith.

“Her complexion was sallow, her tawny hair was thin and streaked, and her bubbling vitality had given way to the slackness of age.” That’s how she looked when she entered the hospital, according a Tribune reporter.

On May 30, she died, and the Tribune’s headline told the story: “’Chicago May,” Famous Woman Crook, Is Dead.”


Patrick T. Reardon



This article initially appeared in the Chicago Tribune on 11.20.16.

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