Old-School Show-Off: Chicago May, Queen of Crooks

Tori Telfer
Jun 13, 2017 · 11 min read

Chicago May would be appalled by her own Wikipedia entry. “Occupation: prostitute,” the page snaps. It claims that her crimes were “mostly of a petty nature” and concludes her brief and colorless entry by saying that she ended up in Detroit “virtually destitute” and “no longer young.” But when May, in her mid-fifties, sat down to write her memoir in 1927, she presented herself as a nervy member of an international gang that moved huge sums of money across the Atlantic, an adulated con artist who almost never actually had to sleep with her victims (unlike her less skilled female compatriots), and a straight-talking crook who made so much money that she could pass as a member of high society.

By her own telling, May was a heartbreaker and a bank robber. “Well-preserved,” she claimed. And kinda sorta reformed. She had seen the light — or rather, she had seen the money, and figured that by now there was more cash in a tell-all book deal than in pulling off a few more cons. Chicago May, Her Story: A Human Document by “The Queen of Crooks” was published in the spring of 1928, but its bluster was a façade: May was destitute and slowly dying of cancer. She passed away the next year at the age of 59, thoroughly worn out by crime.

The Queen of Crooks tells us she was born Beatrice Desmond on a farm near Dublin on November 25, 1876, but other sources call her May Duignan and give her birth year as 1871. (She was probably deliberately obscuring her identity in order to protect her family.) May was the only girl in a family of seven children and was constantly getting in trouble at school for refusing to do thing she found ridiculous—like kiss the ground as a sign of penitence. By the time she hit adolescence, farm life was far too confining for her, and her parents were getting too strict for her liking. So in 1889, 13-year-old May filched sixty pounds from her dad’s money box and sailed off to America on a steamship. “It never entered my head that I might not succeed,” she declared.

She blew some of that money around New York City, reveling in the chaos, eating littleneck clams for the first time, and turning down propositions from men who assumed she was for sale. “They weren’t going to take me for a greenhorn!” she crowed. After a few weeks of this revelry, she started running out of money and headed to Lincoln, Nebraska, to live with her rancher uncle. He wasn’t thrilled to see a red-headed teenager standing on his doorstep, and so he put her to work in the kitchen; May wasn’t thrilled to work in the kitchen, and so she took up with a bunch of wild local kids. “I wanted to ride around and see the sights,” she wrote. “Not that I didn’t. Only I wanted more of it!” The hottest one of her new friends was 21-year-old Dal Churchill: “An Adonis, a model for a Greek statue.” Before long the two of them were running away to shack up together. May was just 14.

Dreamy Dal Churchill just so happened to be a member of the infamous Dalton Gang — outlaws who robbed banks and held up trains all around the West. This was May’s first glimpse into the thrilling, glamorous, and wildly lucrative side of crime: the wads of cash, the parties, and the handsome, reckless men. (“I enjoyed this part of the game exceedingly,” she says. “I liked what money could do.”) Often, the gang would send May to stay with one of their sisters in Chicago as they pulled off a heist somewhere in the West, in order to keep her out of the way. Dal, who had warned her that life with him would be “full of nerve-wracking experiences,” soon suggested that they get married just in case she got pregnant and he got killed. His suggestion was eerily prescient. Not long after their marriage, Dal went off to Phoenix to rob a train, leaving May alone in Chicago. The heist was a failure, and Dal was wounded, captured — and lynched.

It was like a switch flipped in May’s head. Suddenly, crime wasn’t just a wicked thrill, but a means of avenging herself of the entire system that had conspired to take away her man. The young widow made up her mind to become the best criminal she could be, fueled by her “deep and abiding certainty that society, as such, was my enemy.” She was already stranded in Chicago, and so she started there, moving deeper into the city’s red-light district, the Levee. “When you want to go wrong,” she mused, “it is very easy to accomplish your purpose.” It was in Chicago that she started to make a name for herself for the variety and cleverness of her cons, as well as for her nerves of steel. “The Greatest Living Woman Thief,” headlines would call her at the end of her life.

Image: Chicago Tribune Archives

May was the queen of the confidence trick, and her victims were mostly rich, naïve men. She would lure them into a specially designed bedroom (called a “creep joint” by tricksters in the know), where another criminal was hiding under the bed, or in a trunk, or behind a greased panel in the wall. Then, once the man was undressed and occupied on the bed, May’s partner would slip out of hiding and go through the man’s pockets, replacing his thick stack of bills with a stack of similarly sized cut paper. Other times, May would play the “badger,” which meant luring a man into a compromising position by fainting and then asking that he see her home — where another criminal playing the role of her husband would suddenly burst through the door and extort money from the man for perceived wrongs done.

Many of her victims were upper-class men — rising young lawyers, for example — who couldn’t come forward and accuse May in court for fear of ruining their immaculate reputations. This meant that blackmail was often too easy to resist for May, and she would drain money from her flustered prey for months. (“What was a poor girl to do with such a sheep, baaing to be shorn?” she mused about one particularly dumb fellow.) The Chicago Tribune claimed that May changed the art of blackmail entirely by introducing a camera into the whole jig.

After exploiting the “goldmine” of innocent tourists who flocked to the Chicago World’s Fair in 1893, May took off for New York to look for bigger game, traveling first class the whole way. She loved to flaunt her wealth by dressing well, reading as much as she could, and hanging out with high society whenever she got the chance. She claims that she bantered with Mark Twain and met the famous actors DeWolf Hopper and Henry Dixey. May seemed to feel that not only was she just as good/pretty/clever as the rest of high society, but she was better: a self-made woman, an individualist, able to move among the wealthy undetected. “I worked hard to make myself a master workman,” she says, and this idea of herself as an expert criminal was integral to her sense of self. She was no common thief; she would never have listed “prostitute” as her occupation. In fact, years later in a British court, she gave her vocation as, simply, “artist.”

When New York grew a little too hot for her, she sailed over to Europe and began running her business in a trans-Atlantic fashion, keeping up with various schemes in both London and New York. For example, she loved a good “breach of promise to marry” con. In those days, a proposal was considered a legally binding contract, so a jilted woman — or, in May’s case, a woman pretending to be jilted — could threaten litigation. She was able to keep these sorts of things bubbling in both cities at the same time, probably by continually sending her victims threatening letters. It was in London, in the spring of 1901, that 25-year-old May locked eyes with Eddie Guerin — a very hot, very bad news Irish-American criminal — over the casket of one of their criminal pals. “Both of us were good-looking, healthy, vigorous, well-dressed specimens of our respected sexes,” she boasted. The two of them quickly became an item.

Like May, Eddie had a temper and a lust for revenge, and he was currently mad at the entire country of France, as he had just spent ten miserable years in a French prison. Before long, he and May were hatching a plan to rob the Parisian branch of the American Express Company in order to show France what was what. The heist was initially successful, and they made off with at least several thousand dollars, but the lovers had aimed far too high with this plot. They were captured as they tried to escape on a train back to England.

Eddie was given a life sentence and flung into one of the most infamous prison in history: Devil’s Island, the “Green Hell” off the coast of French Guiana, surrounded by jungles full of predatory ants and rivers full of piranha. May got off easier; she was pardoned after two years and nine months of a five-year sentence — served in several French women’s prisons — thanks to a touch of bribery and a couple of influential friends who pulled some strings for her. When Eddie, against all odds, actually managed to escape from Devil’s Island in 1905 after about three years locked up, he tore back to England, ranting and raving. He was convinced that May had ratted him out to the police, and wanted to cut off her ears, or — May claims — douse her with acid. (“Anything to disfigure my beauty!”)

May had a new boyfriend by this point, Charlie Smith, and when the two of them ran into Eddie in the streets of London in June 1907, both men began shooting. Eddie’s gun jammed, while Charlie managed to shoot off two of Eddie’s toes. The whole skirmish was pretty harmless for this trio, but both May and Charlie were charged with attempted murder: life for Charlie, fifteen years for May. “I laughed,” says May, upon hearing her sentence, “so as to show the minions of the law that they hadn’t broken my spirit, and to show my sympathy for Charlie” — who had flung himself on the judge as if to kill him, raging with sick horror. Charlie eventually ended up in prison in California, and May would love him — and hope to marry him — for the rest of her life. Presumably, she was over Eddie, who had gone slightly mad in his green hell.

Aylesbury Prison in Buckinghamshire, England was a miserable place for an Irish lass accustomed to fine clothes, international travel, and utter freedom. There was an extremely realistic eye carved into the ceiling of each cell, with a little panel in the middle that could be slid open so that the prison matrons could peer through, and it nearly drove the prisoners mad. “You can get used to nearly anything, but you never quite got over the horror of being constantly watched,” May noted. The only positive thing about prison was that it gave her the chance to read, and she devoured everything from The History of the Decline and Fall of the Roman Empire to Dickens novels, which she loved for their hilarious portrayal of crooks. Eventually, her sentence was reduced to 10 years and she was sent packing back to the States, with her wild youth firmly behind her.

After prison, May grew increasingly existential. “What had become of the considerable sums I had filched from society?” she asked. She now barely had enough money to rent a room. She had trouble getting a job, and eventually ended up in Detroit. The once-lucky May — now in her fifties and in poor health — couldn’t catch a break anymore.

The rest of the world wasn’t done with her, though. In 1927, August Vollmer, the former head of the Berkeley California Police Department, took her under his wing — she says he visited her while she was laid up in a prison hospital in Detroit — and encouraged her to “go straight” and write her memoirs. (Seedy memoirs written by former crooks were very popular in those days, with their vague whiff of redemption and titles like Why Crime Does Not Pay. Even Eddie Guerin wrote one, called I Was a Bandit.) May was no writer, and had difficulty following a narrative through-line — her memoir jumps all over the place — but she tackled the project gamely. She and Vollmer corresponded regularly, and Vollmer also kept her updated on the status of her old boyfriend Charlie Smith, who was serving his long sentence in California.

Meanwhile, another crook was about to enter May’s life. Netley Lucas was an infamous British con man who’d been active in the 1910s and ’20s and then loudly crowed that he had reformed and was taking up journalism. By 1927, he was schmoozing around New York, where he’d just published a book about famous female criminals called Ladies of the Underworld. It was there that his publisher came up with a genius PR plot: Netley Lucas and Chicago May should get (fake) engaged. The press went wild over the odd couple, noting gleefully that May was a good thirty years older than Lucas. The American Weekly declared melodramatically that the “greatest living woman thief” was now the aging muse for this youthful “student of crime.”

May, who used to love the spotlight, trudged dejectedly through this final burst of notoriety. “I am sick and weary of life,” she wrote to Vollmer, and begged him to reassure Charlie Smith that the engagement wasn’t real. Lucas noted with shock in his own memoir, My Selves, that May was no longer the “beautiful adventuress” of days past — instead, she lived in a hotel room full of booze and cigarettes and dirty magazines, dying of cancer, and “soliloquizing in maudlin fashion over the past.” But the notoriety of the fake engagement helped her find a publisher. Her memoir came out in the spring of 1928.

By 1929, she’d moved to Philadelphia to have an operation for an “abdominal disorder,” and it was there that she was finally reunited with Charlie Smith, who’d been released. The two old lovers hadn’t seen each other for twenty-two years. They made plans to marry—perhaps dreaming of a deliciously normal, crime-free future together with a house and a dog and a garden—but May was much sicker than she or Charlie realized. She died in the hospital so unexpectedly that the nurses didn’t think to call Charlie back to her side until it was all over. “I have loved her for more than twenty years,” said Charlie, on hearing the news.

There’s no soaring redemption at the end of May’s story. The heady days of crime were long over, and she’d watched most of her friends become addicted to dope or simply sink into destitution. (Guerin, who outlived her by eleven years, died poor and obscure.) Crime had been her life’s work, the only job on her resume, but she was living proof that sometimes it added up to nothing at all.

The book ends with a recitation of facts about herself, carefully calibrated to portray a specific type of brave, cultured, autonomous womanhood: she doesn’t like to get drunk, but when she does, she gets drunk on whiskey; her favorite liqueur is Amer Picon, a bitter orange aperitif from France; she speaks English, French, Portuguese; she’s not a kleptomaniac, but likes the security that money provides; she is “well-preserved” and proud of it. She was sick while she wrote those words, but you wouldn’t know it. “I have had no regrets — except when I was caught,” she writes. “I am not really sorry I was a criminal.” Even with death hiding somewhere in the room, waiting to trick her, Chicago May admits no defeat.

The Awl

Be less stupid.

Tori Telfer

Written by

Author of LADY KILLERS: DEADLY WOMEN THROUGHOUT HISTORY. Host of a true crime podcast: criminalbroads.com.

The Awl

The Awl

Be less stupid.

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