‘The most dangerous woman in the world’

Published in 18th–19th - Century History, 20th-century / Contemporary History, Issue 4 (Jul/Aug 2005), News, Volume 13

DUIGNAN, Mary Ann (‘Chicago May’) (1871–1929), criminal and prostitute, described by contemporary tabloid journalists as ‘the most dangerous woman in the world’, was born on 26 December 1871 in Edenmore townland, Dromard parish, Ballinamuck, Co. Longford, the eldest among two daughters and three sons of Francis Duignan and Anne Duignan (née Gray); the pet name ‘May’ was applied to her from childhood. The family lived in respectable and comfortable circumstances in a two-storey house on a 140-acre farm. Educated at Edenmore national school, at the age of eighteen she emigrated to New York. After working briefly as a dishwasher, she obtained a role as a chorus dancer in a hit musical, ‘The belle of New York’. Introduced to prostitution by fellow chorus members, for a time she continued her substantially less lucrative stage work as a device for attracting clients. She beguiled and married a young, well-to-do army officer, James Mountgomery Sharpe, but broke with him after three months, taking $10,000 of his fortune.
Amassing large sums by allying prostitution with robbery and blackmail, she was soon a familiar figure among the gamblers, gangsters and courtesans in the garishly fashionable clubs of New York’s notorious Tenderloin district. A buxom 5ft 6in. in height, with blue-grey eyes and an abundance of dark auburn hair, she radiated wit, charm and a deceptive air of innocence. Working alone or with accomplices, she robbed her drugged, intoxicated or distracted clients; a favourite ploy was to fling a naked victim’s clothing and wallet from a hotel window to a confederate in the street, and then bolt from the room. She was particularly adept at the ‘badger game’ of blackmailing wealthy clients, often using compromising letters or photographs; victims made substantial and repeated payments to avoid exposure or the threatened wrath of her fictitious ‘enraged husband’. Operating in cities throughout both North and South America, employing numerous aliases and moving frequently to avoid recognition or prosecution, she supported an opulent lifestyle of costly jewels and furs, luxurious hotels and restaurants, and first-class travel. Her sobriquet ‘Chicago May’ derived from a period based in that city (1891–4), preying on visitors to the World’s Fair.
After years of evading, bribing or charming law officers and judges, Duignan ran foul of the New York police and skipped to London (1900), making it the base for rackets throughout Europe, her victims including prominent industrialists, jurists, politicians and aristocrats. With her lover and criminal partner Eddie Guerin, an international jewel thief and safe-cracker, and two other accomplices, she robbed the American Express office on Rue Scribe, Paris, of $300,000 (27 April 1901). Although fleeing successfully to London with her own and Guerin’s share of the haul, she was arrested several weeks later when, bizarrely, she visited Guerin, who had been apprehended speedily, in a French prison. After serving half of a five-year sentence in Montpelier, she seduced and blackmailed the prison doctor into signing a medical certificate for her release.
Based again in London, she reunited briefly with Guerin after his escape from Devil’s Island. When the couple quarrelled violently—Guerin allegedly ‘thrashing’ her and threatening her with a gun—Duignan informed on him to British police as a fugitive from French justice (April 1906). On Guerin’s release a year later following the quashing of a French extradition request, Duignan accompanied her new lover, Charlie Smith, as he fired six gunshots at Guerin on a London street, wounding him in the foot (15 June 1907). After a sensational trial at the Old Bailey, which titillated the public with lurid revelations of underworld activities, Duignan served ten years in Aylesbury prison for attempted murder (1907–17).
Deported to the USA as an American citizen by marriage, she returned to prostitution and related racketeering. Faded in looks and glamour, in poor health and suffering from alcoholism, she experienced indifferent success and frequent scrapes with the law. Engaged to marry her old confederate Charlie Smith, who rejoined her after 22 years’ separation, after surgery for an abdominal disorder she died in hospital in Philadelphia on 30 May 1929. Despite her enduring capacity to charm men and lure them into her confidence, May Duignan was a ruthless and unscrupulous criminal, capricious, vengeful and capable of brutal violence.

Lawrence William White is a research assistant with the Dictionary of Irish Biography.

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