The Story of Chicago May

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A portrait of the legendary woman outlaw describes her childhood in post-famine Ireland, work as a confidence trickster and grifter in America, love affair with a big-league criminal, successful robbery of Paris's American Express, imprisonment, and later years. By the author of Are You Somebody? 75,000 first printing.

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Rating(4 / 5.0, 84 votes)
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84 reviews All reviews
April 26,2025
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Ultimately this cannot be read as a stand alone book, for it's strongly connected to Ms. O'Faolain's memoirs and is as much about her own thinking and feeling as it is about the nominal subject. It's beautifully written, as are all of her books, but in the end, I tired of it, because it seemed to me that she was wasting a lot of effort on a subject that was ultimately unworthy of her.
April 26,2025
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The author didn’t do a great job of making me care about the subject. It was painstaking to get through.
April 26,2025
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An interesting yet highly speculative account of the life of 'Chicago' May Duignan, a young Irish girl who ran away from home in the late 19th century, away from her rural life. Crossing the Atlantic, she soon became a notorious figure in America. This notoriety was clearlyl deserved - May was a well-known confidence trickster, thief, prostitute and sometime showgirl. She spent a considerable amount of time behind bars as a result of her career choices, but she was a strong, intelliegent and determined woman (although, like many intelligent women, she seems to have had a weakness for dangerous and manipulative men), and appears to have been a thoroughly fascinating, feisty character. O'Faolain neatly puts May's life and exploits in their historical context, but the sheer amount of speculation and what can only be called fantasising about May's life on the part of the author becomes rather wearing for the reader, and leaves it as a volume somewhat slight in its content. Not as good as it could have been.
April 26,2025
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Fascinating. Nuala did it again. She "talks" to her reader when she wrote. Nuala read about Chicago May when she lived in Ireland and couldn't find enough info about her. May was born in Co. Longford, left her family home with all their savings. She went to Chicago and became a prostitute and a wanted criminal. She was married about four times and imprisoned in France and jailed in the States. She did return home once but her family was ashamed of her. Nuala followed May's footsteps to see what May saw and researched all the records and wrote May's story to add to the story that May had written about herself (which Nuala noted was poorly written).
April 26,2025
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I have been wanting to read this book for a long time, as I am a fan of O'Faolain's writing, and I also find the lives of infamous people fascinating - where did they come from, how did they end up doing whatever it is that made them famous, etc. This book was a nice combination of the two. In addition to that, it was my first choice for the "What's in a Name" reading challenge, serving as a book with a place name in the title.

The story begins as May Duignan, 19 years old, is running away from her family home in Edenmore, County Longford, Ireland. Edenmore was a small town and many of its inhabitants, including May's family, were barely eaking out an existence. She has sixty sovereigns in her pocket, and a desire to "get out of town." The year is 1890.

By the time May arrives in America, she has already to make do and be quick-witted; when she is asked who will be responsible for her here, she names an uncle that she doesn't really remember, but that she knows emigrated to America years ago, and is living in Nebraska. O'Faolain's research showed no one with May's family name living in Nebraska at the time - however, throughout her life, she gave different names at different times, depending on the situation, so there is the chance that she didn't use her real name upon entry to the country.

May makes her way to Nebraska, and there her life as part of the criminal element begins. She falls in love with a man named Dal Churchill, who is a known thief, highway robber, etc., in the rough and tumble area which was then thought of as the American West. From here to the end of the book, we follow May to several cities in several countries as she does what it takes to survive. O'Faolain theorizes that, because she has no formal education or skills, her choices are limited. She looks around, and realizes that being a con artist, or a prostitute, or simply a petty thief is more financially lucrative than many of the jobs open to the Irish during that time period. She does have a brief period of marriage and respectable domesticity, but the lure of her other life wins out in the end.

This book was a fascinating read. O'Faolain manages to make May a real person, though not necessarily a likable one. You feel for her, but at a certain point you also realize that she is making decisions for herself, and realizes what the consequences are of being caught. The people who surround her are interesting in and of themselves, and their place in her story and her orbit add to the sense of dangerous adventure that is May's story.

In addition, I enjoyed the aspect of the book which talked about the law enforcement practices of the time, as well as society's changing attitudes towards criminals. There is plenty of corruption to go around, as well as attempts to reform the criminal justice system. There are stories of various members of a family who work for the Pinkerton Detective Agency. There is a description of the "job" in Paris at the American Express Building, which was one of the biggest heists of its time. Basically, there's a little something for everyone here, if social history interests you.

O'Faolain's journey up to the time she writes the book, and once it is written, is also of interest. Her fascination with May Duignan sends her on not just a physical journey from place to place, but a personal one as she comes to grips with some of her own demons related to her late younger brother.

There are ways I think that this book could have been better. There are parts that drag, at least as far as I am concerned. But I found it to be a good read, and a fascinating look at a life that was not necessarily atypical for its time and place.
April 26,2025
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Awkward format interferred with enjoyment of story.
April 26,2025
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The Story of Chicago May (Hardcover)
by Nuala O'Faolain

Feminine sexualization. A biography of a woman in crime. Irish immigrant to America. Prohibition era.
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