Chicago May, the nickname of Mary Anne Duignan, an Irish-born criminal who becomes notorious in the United States, United Kingdom and France, dies in Philadelphia, Pennsylvania, on May 30, 1929. She refers to herself as the “queen of crooks” and sometimes uses the name May Churchill.

Duignan is born in Edenmore, Ballinamuck, County Longford, on December 26, 1871. In 1890, at the age of 19, she steals the proceeds earned by her parents from a recent cattle fair and runs away to Liverpool, England where she buys new clothes and books a ticket to America. Upon arrival in New York City she supports herself by prostitution and picking pockets.

She moves to Chicago to take advantage of the large influx of visitors at the 1893 World’s Columbian Exposition. She teams up with another prostitute. One robs customers while the other is having sex with them. She returns to New York City, where she works as a dancer, but is soon arrested for stealing a wallet, earning her first jail sentence. She briefly marries friend Jim Sharpe but the couple soon separates. After this, she calls herself May Churchill Sharpe. She soon establishes herself with the local criminal underworld, becoming involved in various crimes, mostly of a petty nature, including fraud, assault, brawling, drunk and disorderly behaviour, beggary and pickpocketing.

Duignan has various criminal lovers, but she graduates from petty criminality to major crime when she meets Eddie Guerin, who organises a robbery of the American Express office in Paris. She is imprisoned for her role in the crime. She operates her schemes on four continents and in nine countries. She reaches the height of her career in England when she is taken up by aristocrat Sir Sidney Hamilton Gore, who supposedly proposes marriage to her, shortly before he shoots himself.

After Guerin escapes from a French prison island, he makes his way to London where he meets Duignan again, but the relationship turns sour. She takes up with a burglar named Charley Smith. In 1907, during an altercation with Guerin, Smith shoots him, wounding him in the foot. Smith and Duignan are both accused of attempted murder. She is convicted and sentenced to 15 years. She is released in 1917, and returns to the United States.

By the 1920s, Duignan is living in Detroit and has become destitute. No longer young, she is reduced to propositioning men on the streets and is repeatedly arrested for soliciting and common prostitution. She hopes to make money from her former notoriety by writing magazine articles and an autobiography with the help of a journalist, which is published in 1928 as Chicago May, Her Story, by the Queen of Crooks. Her former lover Guerin publishes his own life story at the same time, under the title I Was a Bandit. She dies at the age of 58 in Philadelphia on May 30, 1929.