The story of Chicago May is famous in the world of criminology. It’s the story of an absconding Irish teenager turned serial criminal operating across two continents who marries for money, cracks safes with explosives and has relationships with some of the Irish-American underworld’s best-known figures. She became a minor celebrity in the British press for her exploits and published a set of memoirs of her criminal past in 1929, the year of her death.
Born Mary Anne Duignan in 1870, Chicago May was one of the more infamous Irish expatriate criminals to ply their trade in the States in the late 19th and early 20th centuries. Running away from home with her parent’s life savings before her 20th birthday, May went to Liverpool, where she bought a ticket for the United States with her ill-gotten gains. You can find her journey in Findmypast’s passenger lists.
Once in the United States, she soon ingratiated herself with the criminal underworld and several of its famous figures, including Dal Churchill, who taught her a lot of the tricks and skills that would come in useful later in her long career. She courted several mobsters, and even managed to work herself into the attentions of an aristocrat and an Army officer, only to divorce him several months later for a $10,000 settlement. She even took on work in a theater as a way of casing out potential victims. Eventually, her criminal past caught up with her in the form of an NYPD arrest warrant, so she fled to London.
In 1900, May met a young Irish mobster named Eddie Guerin, and they begin a relationship after May traveled to Paris for the 1900 World’s Fair, in search of wealthy individuals to rob. Edward Guerin was never too far from crime and notoriety: He appears multiple times in the US, British and even French arrest records.
Guerin was the chief architect of a planned theft from the offices of The American Express Company in Paris. With May as his accomplice, Guerin using a lot of explosives to blow open the safe. However, for this theft, he was caught and imprisoned. May got away, returning to London to find the funds to secure Guerin’s release.
However, after another brief spell in prison for trying to spring Guerin with forged documents, May moved on with her life. She struck up a relationship with a man known as Charley Smith. Unsurprisingly, Eddie Guerin was not too pleased about May and Smith’s relationship when he made good his escape from a French penal colony and arrived back in London in 1907. However, before Guerin can take his vengeance, he was shot by Smith. Both Smith and May are immediately arrested, the shooting taking place in broad daylight in Russell Square in front of two uniformed Police Officers.
May went on to be sentenced to 15 years Hard Labour for attempted murder, serving 10 years of the sentence before her deportation to the United States. Guerin remembered this attack long after the event.
Back in the US, May continued to ply her trade as a prostitute until her death in 1929. Her memoirs, Chicago May Her Story: A Human Documentary by the Queen of Crooks, lay out her career from her humble beginnings as an absconded teenager to a master thief. Why not explore Findmypast’s crime, prisons and punishment records yourself, and work out if any of your family members were master thieves?
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