Queen of Crime – Brian Maye on the international criminal known as ‘Chicago May’

Are some people born to be criminals or do the circumstances of their lives make them so? The Irishwoman who became the notorious international criminal known as "Chicago May" belonged to the former category, according to herself, and her life, which began 150 years ago this year, was certainly an action-packed, colourful one.

She operated under various aliases and her 1928 autobiography, published under the name May Churchill Sharpe, is highly unreliable in factual terms. There she claimed she was born Beatrice Desmond in 1876 but she was almost certainly born in 1871 (the date December 26th has been suggested but that is not definite) and her name was Mary Ann Duignan. Her birthplace was Edenmore, Ballinamuck, Co Longford; she was the eldest of five children of a relatively comfortable family and was called May from childhood.

At the local national school which she attended, she often got into trouble, according to her autobiography, which also stated that she resented her parents’ efforts to control her behaviour.

She was among the earliest to use the growing science of photography for blackmail

At 18, she stole family savings of £60 and made her way to the US. “Nothing was easier than to rob the money box in father’s room,” she wrote, “he could afford to lose it and I needed it.”

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Ending up in Chicago, she became involved in theft and extortion and possibly prostitution; as "a prize graduate in the Chicago school of crime" (her own words), she was given the nickname that stuck with her for the rest of her life. Moving to New York, she became well known in the notorious vice and gambling district, the Tenderloin. "A striking, buxom beauty, five-feet-six-inches in height, with blue-grey eyes, and an abundance of dark auburn hair, she radiated wit, charm and a deceptive air of innocence," according to Lawrence White in the Dictionary of Irish Biography.

Various ploys were used to exploit clients, a favourite of which was to throw a naked victim's clothes and wallet from a hotel window to an accomplice in the street and then run from the room. She skilfully blackmailed richer customers, using letters or photographs; indeed, she was among the earliest to use the growing science of photography for blackmail. She was active in cities throughout the US and South America, keeping on the move and living the high life on the proceeds of her crime.

According to her own account, she married a Chicago criminal called Dal Churchill shortly after arriving in the city but he was killed a year after their marriage. In 1899, she married James Montgomery Sharpe, from a wealthy New Jersey business family, but the marriage was short lived; both of those men's surnames were added to her long list of aliases.

Deported to America, May resorted to her old ways but declining health and alcoholism took its toll

Under pressure from the authorities in New York, she moved to London and it became the base for her activities in Europe and North Africa. Businessmen, members of the legal profession, politicians and even aristocrats – all were fair game to her, such that police files once described her as "the worst woman in London". She teamed up with Eddie Guerin, an international jewel thief and bank robber and they stole a huge amount from an American Express office in Paris. She managed to get to London but he was quickly caught and when she returned to France to visit him in prison, she was arrested and sentenced to a five-year term, serving half of it before being released.

Back in London, she claimed she raised the money that helped Guerin's escape from the notorious Devil's Island prison. Following a fierce quarrel, they separated. She enlisted the aid of an accomplice and they attempted to shoot Guerin; for this she served 10 years in Aylesbury Prison, where she met Countess Markievicz, sent there for her part in the Easter Rising.

Deported to America, May resorted to her old ways but declining health and alcoholism took its toll. In a prison hospital in Detroit, she was advised by the pioneering criminologist August Vollmer that she could mend her ways by writing about her criminal life and living off the royalties. Five articles in the New York American Weekly were very successful and were followed by her autobiography, Chicago May, in 1928. She got little chance to enjoy the money the publication yielded because, following surgery for a gynaecological condition, she died in Philadelphia general hospital on May 30th, 1929, and is buried in an unmarked grave in the city's Fernwood cemetery.

Variously described as “the most notorious woman in Europe” and “the most dangerous woman in the world”, she revealed no remorse in her autobiography for her actions.

Who can say what motivated them?