Chicago May: Thief, Extortionist And The Queen Of Crooks

The scene is a farm in nineteenth-century Dublin, Ireland. A peasant girl with ambitious dreams well beyond her means is trapped in the monotony of the household. Her only options to get out of the confines of the monotonous peasant life? Marriage or emigration. Half the population of Ireland, after the famine, emigrated in search of a better life. A 13-year-old May Duignan did the same. Except she did it by stealing her family savings.

Sailing off to America on a steamship, the peasant girl made her transatlantic trip travelling in first class. With an early taste for living among the gentry, May Duignan, also called Beatrice Desmond sometimes (her real name remains a mystery), revelled her life in New York City but eventually ran out of money to support her lavish lifestyle.

While staying with an uncle in Nebraska, she met the 21-year-old dreamy Dal Churchill, a member of the infamous Dalton Gang who robbed banks. Seeing the thrilling and glitzy side of crime with bundles of cash, handsome men, and fancy parties enthralled May. The two got married, and Dal left her to rob a train. But the mission failed and ended up with Dal lynched and May left alone with nothing to survive on.

This was the turning point in her life, a life that earned her the title of “The Most Dangerous Woman in the World.”

Adopting the name “Chicago May,” she, like many other women, made her way into the red-light district of the city. Finessing her conning skills, May preyed on upper-class young men. Luring them into discreet corners, she would take the huge wads of cash the men had in their suit pockets and replace it with a stack of paper. Calling her the “badger,” a con woman who seduces her victim with sex and then robs them before anything could happen.

Blackmailing was too easy for her to resist, especially when the rich and naïve men were ready to give up their wealth to protect their reputation. With a knack for dressing well, May loved to show off her wealth and spend time with rich and sophisticated company whenever she could. May was no common thief. She has singlehandedly fooled an entire class, flipped the class divisions of society to navigate through life, and succeeded. When the cops got too close to her, she took off.

Sailing off to Europe next, she began extracting money from men pretending to be jilted lovers, betrayed by the false promise to marry (back then, a proposal was a legally binding contract). She kept her business active in London and New York simultaneously.

In London, Eddie Guerin, another lover in a series of men in her life, and May became a thing. The two robbed the American Express Company in Paris and made off with at least seven thousand dollars. But the deal was too good, and the two were captured.

While Eddie got a life sentence, May was pardoned after two years and nine months of a five year sentence after seducing and blackmailing the prison doctor. Later in life, she was arrested again, spending ten years in Aylesbury Prison in England.

When she finally returned to America, the glamorous life she had expected did not exist. In Philadelphia, she spent her last days reunited with her lover and literal partner-in-crime, Charlie Smith. While the dreams of a crime-free future filled with love never graced May, who died in a hospital due to cancer in 1929, she did live a life full of, well, pretty much everything. In her memoir titled “The Queen of Crooks,” she wrote, “I am not really sorry I was a criminal.”