Skip to main content
Create interactive lessons using any digital content including wikis with our free sister product
. Get it on the
Pages and Files
Agrippina the Younger
Aung San Suu Kyi
Catherine the Great
Eleanor of Aquitaine
Hildegard of Bingen
Joan Of Arc
Mary Ann Cotton
Add "All Pages"
CHICAGO MAY- A CROOK: DANGEROUS AND FEMALE
2) Early Life
5) Travel and birth locations
6) Legacy, history and achievements
8) Primary Sources
10) Recommended reading list
Described as "
the queen of crooks",
Mary Ann "Chicago May" Duignan was born in Longford, Ireland 1871 to Thomas Duignan and Mary Elizabeth Brady.
During her fifty nine years of life, she was most famously known for being a notorious international criminal who operated her schemes on four continents and nine countries.
Mary Ann Duignan was born in County Longford, Ireland as the daughter of Thomas Duignan and Mary Elizabeth Brady on the 26th December, 1871. She was the eldest among two daughters and three sons and the pet name "May" was applied to her from childhood but more detailed information of her family background is unknown. Her family lived in respectable and comfortable circustances in a two story house on a 140-acre farm. Educated at Edenmore National School, at the age of eighteen, she migrated to New York, taking her family's entire assests with her.
After stealing her family's entire assests, May Duignan decked herself out in the latest fashions and bough a first-class steamer ticket to Amerca.
At the age of 18, May emigrated to New York and worked briefly as a dishwasher before she obtained a role as a chorus dancer in the famous musical, "The Belle of New York". From the other chorus members, she was introduced into the world of prositution where she continued her substantially less lucrative stage work as a device for attracting clients. She then married a young army officer, James Mountgomery Shape, but divorced him after three months, taking $10 000 of his fortune.
Described as a "buxom" woman at 5 feet 6 in height, with blue-grey eyes and an abundance of dark auburn hair, she radiated wit and charm, amassing large sums of money by allying prostitution with robbery and blackmail. She became a familiar figure to the gamblers, gasters and courtesans in the fashionable clubs of New York's notorious Tenderloin district.
May Duignan received her sobriquet, "Chicago May", derived from a period based in the city of Chicago, preying of visitors to the World's Fair.
Operating in cities throughout both North and South America, she employed numerous aliases and moved frequently to avoid prosecution or recognition. She lived a luxurious lifestyle, consisting of costly jewels and furs, opulent hotels and restaurant and first class transport.
Afte years of evading, bribing or charming law officers and judges, Duignan ran foul of the New York police and moved to London in 1900, making it as the base for rackets throughout Europe. Her victims included prominent industrialists, jurists, politicans and aristocrats.
With her lover and criminal partner, Eddie Guerin, an international jewel theif and safe-cracker, she and two other accomplices robbed the American Express office on Rue Scribe, Paris of $300,000 on the 27th April, 1901.
She succesfully fleed to London with her and Guerin's share of the haul but was arrested several weeks later when she visisted Guerin who had been captured and deported to a French prison.
After serving half of her five year sentence in Montpelier, she was said to have seduced and blackmailed the prison doctor into signing a medical certificate for her release.
Deported to the United States as an American citizen by marriage, she returned to her original work as a prostitute. However, due to her age, her beauty had faded and she suffered from alcoholism, she experienced low levels of monetary success and often, had a few scrapes with the law. Chicago May died after surgery for an abdominal disorder in hospital in Philadelphia on 30th May, 1929.
Despite living a luxurious life, Chicago May suffered from many physical illnesses, becoming reliant on alcohol, thus developing alcoholism. Even at her old age, Chicago may stll continued her work as a prostitute until her deap in Philadelphis, 1929 after a surgery for abdominal disoder.
Travel and birth locations
Chicago May was know for working internationally for her crimes, located across four continents and nine countries. She was noted to have travelled to Cairo, Paris, Belgium, London and cities across both South and North America.
TRAVELLED LOCATIONS OF CHICAGO MAY
Chicago May was born in Longford County, Ireland
Legacy, history and achievements
Chicago May's legacy and impacts to history is sometimes labelled as "great" and othertimes, just noted as "petty crimes". However in an historical perspective, Chicago May can be considered to be one of the most greatest masterminds of female crooks.
The reason in which why May Chicago Duignan had paved her mark into history is due to her most famous crime, the robbery of the American Express where she stole $300,000 at once. Chicago May had many times excaped difficult situations, exuding herself from jail, police and even furious wives, proving that she was, in ways, above the law. Also, her ruthless, not to mention ingenious, methods of fulfilling her desires, Chicago May became one of the most feared, notorious yet oddly respected villainess of the early 20th century.
“I was not as smart as I thought I was.”-
This is a quote, made directly by Chicago May Duignan in her autobiography, explaining her actions before her arrest in1901. This quote explains to the that Chicago had overestimated her cunning, resulting to her arres. Chicago May was famously known for being of high intelligence, however, this quote contradics the theory, therefore, giving more information of the character, Chicago May. Also, this quote, being a direct quote of Chicago, is an excellent source for insight to the minds and inner workings of Chicago May, who clearly considered herself as clever.
The picture above is a picture of La Roquette women's prison, the first prison that Chicago May had been to. This jail plays a major role in Chicago's life as it was the first time Chicago had not managed to evade the law. This source, though not directly, shows the slow, yet coming demise of Chicago's career, which steady went downhill afterwards.
The picture above is a illustrated image of Chicago May, taken during a trail for attempted murder in 1907. The image is one of the few surviving pictures that depicts Chicago's face. This source can reveal to the historians of the types of experiences that Chicago had faced, ranging from a prostitute in brothel houses, to a convicted murderess.
Chicago May, clever, beautiful and wily, is potrayed usually as a ruthless crook, yet the primary sources above provide different perspectives of Chicago's life and who she was as a person. The first source shows to the readers and historians that Chicago May sometimes had lapse, making mistakes that ultimately lead to her demise and the end of her career, giving a new side to her character. The second source, a picture of the jail she had spent three and a half years of her life in, paints us a picture of her background and the types of experiences she had lived through. The living conditions throughout her life had not remained steady, and that is demonstrated by the image of the jail, which proves to historians that she did not live in luxury for her entire life. Source three depicts Chicago's physical appearance through a painting/cartoon during her murder trial. The artist had capture her engimatic and slightly disdainful expression, firming the idea that Chicago was an aloof, if not arrogant, character. The three sources shows different perspectives of Chicago May, showing her more humane side as well as her life as the coolly detatched, mastermind crook.
Chicago May, 1907 at court
Birthplace of Chicago May
Jailhouse in which Chicago had dwelled in for 3 and a half years
Mug shot of Chicago May, taken during her middle age
Recommended Reading List
Article with a brief summary of Chicago May's life with some pictures included.
"The Story of Chicago May"
by Nuala O'Faolain
A biography of the life of Chicago May, following her life from Ireland, New York and to her death.
"Hell Hath No Fury: Famous Women in Crime"
by King, Betty Nygaard
A book on notoriously famous female criminals.
An article written in 1907, writing of the imprisonment of Chicago May and Eddie Guerin.
True or False
a) Chicago May is her full name (T/F)
b) Chicago May had originally gone to New York in hopes of becoming a prostitute (T/F)
c) Chicago May had blonde hair (T/F)
d) Chicago May stole $398000 in the American Express robbery (T/F)
e) Chicago May died of liver cancer due to her alcoholism (T/F)
4) Word Search
help on how to format text
Turn off "Getting Started"