Book review of Chicago May's Story💸🚓❤️🩹🏥🪦
+ Why I'm glad AI didn't write this biography + the Mountain-view Midpoint story structure
I chose this photo from May’s memoir to show you because it turns out this might be the only genuine, verified photo of her. She hid her face from cameras for most of her life, as good thieves do. At least I know this one is authentic because her actual photograph is something the publishers could not conveniently forget to fact-check. As for the rest of her memoir, well, let’s just say that sensationalism sells, so she told the truth where she had to and romanticized the rest as needed. The benefit of reading The Story of Chicago May biography by Nuala O’Faolain is that I got the background fact checking of May’s perspective against reality, as investigated thoroughly by an Irishwoman who knows and understands where Irish May was from, a person with no need to color the tale this way or that.
Also, in honor of May’s Irish heritage (and my own sliver of Irishness), prepare yourself for liberal use of the word “feck.” (Yes, it means exactly what it sounds like.)
But first, why would this book have been a disaster if written by AI?
So glad you asked.😏 Essentially, May left a trail of aliases, men, stolen money and valuables so long, and she moved around so often, that the records left behind about her in the 1890s to 1900s are a tremendous fecking mess. To say that the records contradict each other was only the tip of the iceberg of problems that the author Nuala faced when researching May. The biographer Nuala had to travel to places where May lived, sift through multiple sets of police records, and spoke to various members of her family and people who knew her to try and piece together the whole picture and read between the lines. The devout Catholics of her birthplace were horrendously ashamed of May’s criminal legacy and weren’t about to share much about why she ran away.
Then to make it even more complicated, one of the men May really did love also wrote a memoir in a desperate attempt to make money like she did after he got out of prison again. This American man that she robbed a bank with in Paris, Eddie, wrote his side of their story…but how would an AI algorithm have presented a combination of lies he obviously told to get a lighter prison sentence? How would the AI have presented the information that Eddie was also May’s vindictive lover who sent one of his friends from jail out to kill her after he believed she had turned him in to the cops (which she may or may not have done)?
Here I have to commend the author Nuala O’Faolain for her dedication to presenting the information she found just the same way that she found it. She lets readers decide. She clearly marked what parts of the story hadn’t been proven by facts, gave good theories about why, and quotes May were appropriate. Nuala cross-referenced all the big moments of May’s life, shows both sides of the story, and points out the idiosyncrasies of people moving through this criminal underworld with all its fluctuating highs and lows. She brings with her the extra knowledge of how women’s testimonies in courtrooms and such were treated by the men ruling the proceedings as well, and all this I thoroughly appreciated.
Now for the review:
Meet the real woman with her real name: May Duignan.
Born and raised in rural Edenmore, Ireland (you haven’t heard of it because, yes, it’s really that small and mostly farms), May decided to tell everyone she knew to “Feck off” in the biggest way possible when she was 19.
In every novel, I study the inciting incident because it tells so much about a character, for it’s not just what pushes them over the edge but when that reveals what drives them. The same is true in real life with real people.
May’s breaking point reveals an unforgettable expression of revenge.
Picture her mam lying in a small farmhouse, on a bed, in the final stages of labor to bring her second daughter into the world in her family full of 3 sons. May is her mam’s household manager, raising all of her younger siblings while her mam is out in the fields with her dad all day. May didn’t have much time to play because as soon as she was able to, she became a mother to all of her siblings. May wanted to emigrate out of the country because she’d heard it was possible to have a life that was NOT all backbreaking work on a small farm with no freedom to do anything else. Her father said no because they couldn’t imagine managing without her, so she was trapped. In this time in Ireland especially, family and God were so intertwined that offending either was an express road to eternal damnation.
It is at THIS time, when her mam is most vulnerable on the labor bed and her whole family is preoccupied with the birth, that May breaks.
Did she see her future in her mam’s suffering there? The author speculated as much. Yet I think it was much more than that because of the few yet powerful words May did write about that time years later:
“It’s not my fault I was born.”
I can hear all the arguments, all the screaming that must have come before she wrote that. I’m close to a lot of people who’ve survived domestic abuse, and I can only imagine the rage that May felt that must have driven her to do this:
May took ALL of her family’s savings.
I imagine her father had screamed at her that he’d never give her any money to go, so she decided, “Fine, then I’ll take it all,” just to get him back.
She ran off to the nearest ship taking immigrants to America. She didn’t leave a note. She didn’t tell anyone goodbye. Her actions shouted out the biggest “Feck you” she could’ve said to her family and everyone she knew. From that day on, she never referred to herself as “May Duignan” again. She started a string of aliases so long that she couldn’t even remember them all. The author speculated that she changed her name to protect her family’s honor. I think it’s more than that. I believe she wanted not only to hide but to cut off all ties she could have with her family because that’s how much she hated her origins and wanted to erase them.
To put it in context to this time and setting, our girl May didn’t just “burn the ships,” she metaphorically set fire to the whole fecking harbor too so that no one would even want to remember her to kill her old identity, completely. She writes of her family years later:
“I have tried to forget them, as I hope they’ve forgotten me.”
Despite all the men she was with both professionally as a lady of the night and in marriages, she never had children like her mother did.
I focus on these defining actions of hers that we can prove because they are the core truths we know. Even newspaper headlines about her sound like myths. May was a compulsive liar, and May completely rewrote her past to pretend she was from an upper-class family. That’s why it was so much work for the biographer to write this. May’s behavior was so wild and unpredictable that the gossip about her was legendary, and I’m sure she wanted it that way with each new alias she took.
May apparently married her first husband in America, who she claims was a train robber in a gang, though there are no records of any man by that name nor any gang like she describes in that area. She mentions he died on a job while he was away, and she went off to Chicago looking for new opportunities.
In May’s memoir, she only writes this one telling phrase about why she chose to start robbing men:
It never occurred to me to look for honest employment. Rewards of steady industry were pitiful…the element of luck appealed to me.
Keep in mind the Ireland that May knew, where so many people had died in the famines or had been kicked out of their homes when English landlords raised their rent prices. Plus, women were at the bottom rungs of society. May hadn’t come all the way from Ireland to end up doing the same fecking menial work she’d done all her life while raising her brothers on the farm, and with just as few prospects. From what I can tell, this was a woman who hardly expected to see tomorrow and was always surprised when she lived another day, who wanted to find out how far luck and risk could take her.
The greatest cause of criminals in the world is a simple thing: hunger. The unending hunger in poverty can turn anyone into a criminal. Even today’s governments would do well to remember that people who have nothing left will have nothing left to lose by rebelling against those in power.
May became an “entrepreneur,” robbing the men who solicited her for sex. Women had to wear so many clothes that in the time it took for her to strip, her friend could take all the valuables out of the chap’s pockets before he knew they were gone. May didn’t even need to sleep with all the men she saw because she stole more than she was paid. She was said to be able to bite the diamonds out of a man’s necktie pin without his even noticing. She even returned to the scene of her crimes sometimes just to be sure they knew it was her who’d robbed them, as if to taunt them. Yet she spent it all as quickly as she got it. It’s possible she didn’t feel so bad for stealing because she must have felt that everyone else had stolen from her and her people anyway, and that was how one “got ahead in the world.”
Her life did end in tragedy, but before we get to that…it’s time for the writing craft analysis of:
🏔️ Mountain-view Midpoint Story Structure 🌋
The author nailed the story structure here by choosing the perfect midpoint, and I realized why the right midpoint can make or break a book.
Some books get by without having a strong midpoint, but I always recognize the mountain-view midpoint because it is fecking memorable. Everything before it suddenly appears in a whole light, and all that happens after is entirely different. You are standing at the peak, and you finally realize just how badly the characters have fecked up or how much trouble they’re in. Bonus points apply for giving the highest emotional high here followed by immediate disaster.
For example:
This is my favorite mountain-view midpoint of all time in Jane Austen’s Pride & Prejudice, where the midpoint is Darcy’s first proposal. You see for the first time the full expression of both characters’ biggest flaws that stop what could have been a great success and turns it into a disaster. Everything Darcy ever said before looks different now, and so does everything after this, giving momentum enough to carry through the rest of the book.
In The Story of Chicago May, our midpoint is the Paris robbery. 💰🏦💸🤑
It is the height of her success, but also the exposure of her greatest weakness that led to one failure after another. This job gave her enough money to never rob again and be wealthy for the rest of her life. May and her lover Eddie (a man who’d recently married someone else before meeting May, not like either of them cared much about that tiny detail though😏) stole today’s equivalent of $600,000 from American Express in Paris. Their crew blew the safe open with dynamite and busted out before the cops could get there. Everyone divided the money, and Eddie and May took off together...
…but then Eddie attracted the attention of cops near the harbor and was arrested. They’d been looking for him because of other crimes he’d committed before. May, as always, managed to look so innocent that no one thought to search her and see how much money she was carrying.
She could have walked away with the money. There was no proof she’d helped them rob the place, and she didn’t have an official criminal record yet. May had walked away from other men many times before.. (Including a husband from an arranged marriage in New York, a Mr. Sharpe who had gone off to war and was later presumed dead). But this time, after pushing away relationships for so long, she had fallen in love, and with a criminal even more reckless and dangerous than herself. Maybe it was because he understood her. Maybe they shared the same dreams and never had to pretend to be “respectable” around each other. Falling in love is the only explanation for what she did next, despite only knowing Eddie for possibly 2 months maximum at that point. To try and save him, she went back to Paris and testified that he was with her all night on the evening of the robbery (admitting her affair with him, who was still married, by the way). The interrogators started asking questions and arrested her as well, and they went on trial together. Despite their stubborn stories that they were together in a hotel and had not robbed the place, more evidence gradually arose. Both her and Eddie were found guilty. May got sent to prison in Southern France for 5 years.
Eddie got far worse because of his earlier crimes as well. He was sent to the prison on Devil’s Island, the French colony where nearly half of the convicts die within their first year, and the other half wish they had.
The French court records reported that as they were being taken out of the courtroom, Eddie and May ran to each other, embraced, and had one last kiss before they were pulled apart and locked up.
These disastrous events destroyed them both.
The severe consequences forced May into grave reflections, and she did change, somewhat. When she got out of prison, she visited her family in Ireland. She had found a way to get some of the money back because accounts show her arriving at that farmhouse as a wealthy woman. Yet they’d all heard about what she’d done because it was all over the newspapers. I’d like to think she brought some money for them to try and make up for what she’d stolen, yet would they have taken her “dirty money”? All we know is that she didn’t stay long, the visit was incredibly awkward, and she never returned to Ireland after that.
May was still in love with Eddie and couldn’t stop thinking about him on Devil’s Island. She sent him money secretly through mutual friends they had in the criminal underworld, and by all accounts, he did receive it because Eddie actually escaped! It was an incredible feat, for only 2 men ever escaped alive.
However, I wonder if it would’ve been better for Eddie if he’d never made it out because he lost most of his sanity in the process. May did find Eddie again in London, and she wrote of him that his time on the island had driven him mad. He was prone to fits of rage, and more dangerous than before.
Yes, everything on the way “down the mountain” (after midpoint) feels like it begins to speed up towards the inevitable.
Eddie and May’s reunion honeymoon trip ended up in flames. He grew more possessive and suspicious of what she’d done to steal money for him from other men. They had one last monumental fight where he kicked her out, fully or partially naked (according to whose account you read), and she may or may not have screamed at him that she’d get him sent back to Devil’s Island.
Facts show that Eddie was arrested shortly after that incident and thrown back into prison, this time in England. He blamed May for the next 15 years of his incarceration and vowed revenge. Eddie did apparently make a friend in prison, Charley, who agreed he would torture and kill May on Eddie’s behalf when Charley was released.
In the oddest twist of fate, Charley succeeds in finding May, yet he falls madly in love with her instead of killing her and confesses everything. Charley even shoots Eddie later to protect her from Eddie. AND even though Charley ends up in jail for this shooting for some odd 20 years, Charley and May stayed in touch until he asked her to marry him when he got out of jail two decades later.
May said yes.
Twenty years later, while May is in her late 50s, Charley makes it to her bedside in the hospital where she’s being treated for many health problems. May has written and published her memoir, which didn’t become the huge moneymaker she’d hoped. She had ended up back at her old tricks to make money in the meantime, yet she always loved Charley. They arrange a wedding at the hospital after her surgery. Yet after the surgery, she does not recover. They pull her back into the operating room on the day of the scheduled wedding, and May passes away before she can marry Charley.
Meanwhile, Eddie ended up as a wandering old drunk on the streets of England, bumbling about, in and out of courtrooms for trying to steal and failing due to his deteriorating health conditions. He died broke, despite publishing his memoir too, and alone.
I imagine May’s life if she hadn’t met Eddie and done the Paris bank heist. Would she have ended up the same way with another man? Or was she grateful for it all in the end because it led her to Charley, the real love of her life? Only May could say.
Thank you for reading😊Let me know what you thought, and feel free to share this post with anyone you like:
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By the way, here are other SubStacks you should definitely look at if you’re a writer:✍️
Misfits & Daydreamers by NYT bestseller Susan Dennard
And my Sci-Fi writer buddy Eric