“The Story of Chicago May” by Nuala O’Faolain

A young Irish farm girl arrives in New York City with big dreams, only to become “a famous criminal in the era of long skirts and big hats.” Nuala O’Faolain tells the story of the life of Chicago May Duignan and also regales her own journey of the discovery of Duignan’s life in her book The Story of Chicago May.

May Duignan was born in County Longford, Ireland, and came of age at a time when “one in every two children born in Ireland”¦was destined for emigration.” And in 1890, when May left for Ireland, with her family’s savings in her pocket, she joined a majority of young, single women who hoped to find a better life in the United States. And here is where May’s story, the stuff of dime novels, really begins. From the rugged west to the Windy City, from New York City to Paris to London to Ireland and then back again, May’s audacity and indomitable spirit only aid her as she cuts a swath through the demimonde as a thief, prostitute, showgirl, blackmailer, bank robber, and would-be murderer.

Following–and often quoting–May’s autobiography, Chicago May, Her Story: A Human Document by the “Queen of Crooks,” and referencing contemporaneous public records and newspapers, O’Faolain paints a vivid picture of the time and the world that May lived in. May leaves much out of her autobiography, and it is up to O’Faolain to reconstruct the more obscure parts of May’s life the best that she can. She does so splendidly, even though she admits that she can only speculate on the things that May left out and why. O’Faolain also provides a perspective on the reality of the immigrant experience for young Irish women, and the options left to them if they fell through the moral cracks like May did.

Not only did May start out as a prostitute, but she also went on to became a “badger” who robbed her prospective clients of their money. “She was famous for her method of biting the stones out of men’s scarf pins while she amorously pretended to bury her face against their chests,” O’Faolain writes. May later goes on to boast that she and her partner, a fellow prostitute, once lifted about $1000–no small amount of money in those days–from a client while he and May transacted business. Such small-time cons and operations marked only the beginning of May’s notoriety. She figured into two infamous cases that would dominate the headlines of French and British newspapers, and she would ultimately serve time in prison for both of these.

The first of these took place during the Parisian Exposition of 1901. May came to Paris with her boyfriend, Eddie Guerin. Along with two other criminals, Eddie engineered the robbery of the American Express office; it was May who hid in the office and opened the door to let Eddie and his cohorts in after closing time. While Eddie was arrested on the train back to England, May got away, only to return to Paris to visit him, and that was when she was arrested for her part in the robbery. May was sentenced to five years of hard labor in a Montpellier prison, but she didn’t serve out her full term. Eddie was sentenced to serve a long term in Devil’s Island. While may maintained in her book that she was amnestied by the French president, Eddie insisted in his autobiography that May used her feminine wiles to convince the prison doctor to sign for her release.

May’s second run-in with the law–this time in England–came about because of Eddie, too. Eddie had escaped from Devil’s Island and went to Europe looking for May, and a few times he found her. After several violent encounters with Eddie, May had had enough. She and her boyfriend, Charley Smith–an old prison friend of Eddie’s who had been hired to kill her but ended up falling for her instead–concocted a scheme to get rid of Eddie for good. Charley shot Eddie from a cab as the latter was on his way home, and while Eddie survived, Charley and May were tried and found guilty of attempted murder. May served her term at the women’s prison at Aylesbury alongside Countess Constance Markievicz, one of the major figures in Ireland’s Easter Rising.

After ten years, and following World War I, an aged, pale-faced May returned to the United States and again began to ply her old trade. But the world was different now, and May found it difficult to make ends meet. She was arrested several times in Detroit for prostitution; the Detroit News of 1926 describes her while she is ill and serving a sixty-day term in the Detroit House of Correction: “The old woman lying in the Detroit hospital, her face streaked with the toll of dissipation and prison walls, was born of a good family in Ireland.”

But it was social reformer August Vollmer who would help her to rebuild her life and try to go straight. He proposed that May should write her autobiography, which was published in 1928 and garnered much publicity and poor sales. Still, May trudged the streets selling herself, because there was nothing else for her to do.

However, things did seem as though they were looking up for May. The arrival of 1929 brought a reconnection with her old flame, Charley Smith, the man who had served twenty years in an English prison for her, the man who had selflessly tried to help her be rid of her violent ex-lover so that she could have some kind of peace. They decided to wed as she lay in a hospital bed in Philadelphia, suffering from what O’Faolain conjectures was “a gynecological problem.” May Duignan, Queen of Crooks, died on an operating table on May 30, 1929, on what was supposed to be her wedding day. So May’s life ended in tragedy, just when it appeared as though she was going to have some kind of happiness at last. May was buried in an unmarked grave in a Philadelphia cemetery.

“The stock-market crash came later in the year that May died; the world changed, and old-style crooks like her were completely forgotten. There was no one to visit her”¦.Adventuresses should prepare for this”¦No marker with your name. Nothing.”

O’Faolain’s narration of the dizzying highs and desperate lows of May’s life is both exhilarating and heartbreaking. Time and again, May Duignan made bids for independence and self-sufficiency when the world was determined that women should not live life on their own terms. Time and again did May rise and fall as she rode out the changes that the Gilded Age, the Belle Eqoque, World War I, Prohibition, and the Jazz Age brought to the world around her: “She has to arrive in some town, pull herself together, lift her bag, and walk down the steps to begin her boring, alienating, uncomfortable, and dangerous work. It was a gallant life in its way, and extremely lonely.” But it is O’Faolain who tells us her story, so that she is remembered. She was a modern, independent woman in a time when such women were considered to be undesirable. And were she alive today, I don’t think she would have been so lonely.

6 replies on ““The Story of Chicago May” by Nuala O’Faolain”

Yes, it would make a very wonderful play!  Unfortunately, May is not the most reliable of narrators, and she states that she she got on well with Constance while they were in prison together.  O’Faolain speculates that while they would have been work detail together, they certainly weren’t BFFs with class differences and social mores of the time.

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You will find it very interesting.  O’Faolain describes everything so well–the locations, the dress, the way of ife.  I’ve always found the Victorian demimonde very interesting.  And O’Faolain describes how May missed out on the social changes that transpired after World War I, while she was jailed.


Moreover, I found the book to be very interesting because of my own Irish heritage, and she really does cover the experiences of Irish immigrants in America.


And I think I am being overly repetitive with the word interesting.

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