Nicolai Constantinovich De Raylan, personal secretary to the Russian consul in Chicago, was on a train to Phoenix, at turns coughing violently and chatting amiably with his physician, W.C. Rowe. It was October 1906, and the 33-year-old De Raylan, a notorious carouser and bon vivant, was headed for a months-long desert air treatment for the tuberculosis he’d been battling for two years. Fully expecting to recover, he’d left behind his wife and stepson, with whom he shared an apartment in Garfield Park.

As the train clacked along the 2,000 or so miles of rails to Arizona, doctor and patient likely talked about Chicago, where the White Sox and the Cubs were facing one another in the World Series, and perhaps about De Raylan’s employer, Consul General Baron von Schlippenbach, for whom the Russian-born De Raylan translated documents and handled various correspondence.

Arriving in Phoenix, he and Rowe checked into the Union Hotel, fancier accommodations than the tent camps where dozens of other tuberculosis patients stayed while taking in the dry Arizona air. Rowe would later tell reporters that he enjoyed spending the ensuing weeks in Phoenix with his patient, who usually dressed in dark trousers and a knee-length coat called a Prince Albert. Rowe would say he found De Raylan to be “a very honest, upright, noble gentleman, a noble-hearted man.”

Despite the doctor’s ministrations, De Raylan’s condition deteriorated within a couple of months. As it did, he became more agitated—though less about the prospect of his death, it seemed, than the circumstances that might attend it. De Raylan emphatically instructed Rowe that if his demise proved imminent, his wife was to be summoned immediately, and only she was to handle his corpse. Pressed by Rowe, De Raylan explained that he and his wife had entered into a religious compact of sorts: that whoever outlived the other would wash the dead body and see personally to its interment.

Rowe was either unable or unwilling to carry out his patient’s wishes. When De Raylan died in his hotel room on the evening of December 18, his wife was still in Chicago, awaiting his return. With no next of kin close at hand, Rowe sent for a pair of undertakers to deal with the body. Then Rowe went to the hotel office to telegram De Raylan’s wife the news of his death.

Soon after, one of the undertakers, a man named Driscoll, rushed back to the hotel to deliver to Rowe another piece of news, one considerably more shocking than that of the death itself: The deceased was not who he claimed to be.

On undressing the body, the undertakers had made a startling discovery: Strapped to the man’s waist was an artificial penis and testicles made of chamois and stuffed with down. Beneath those: a vagina.

Who was this invention named Nicolai Constantinovich De Raylan? And how had this twice-married man about town kept his real identity a secret during the 13 years he’d lived—quite heartily, by all accounts—in Chicago? These were the questions breathlessly posed by local reporters the day after De Raylan died. “Death, that strange mystery, opened another mystery hardly less strange,” the Arizona Republic intoned the next morning in an article headlined “A Man in Lifetime, a Woman in Death.”

Within days, the Chicago press had picked up the story. On December 20, a front-page article in the Inter Oceanoffered a detailed account of De Raylan’s life in Chicago, based on interviews with those who’d known him, though the piece offered little about what may have preceded his arrival on our shores. “Baron’s Confidential Secretary Pictured by Friends as Oddly Effeminate,” blared a headline beneath a photo of De Raylan and his wife, Anna. “Wife Is Indignant.”

The article itself seemed at certain points to insist on the reassuring notion that telltale signs had been there all along, while at other moments it described De Raylan’s acquaintances as utterly flabbergasted. “While they admitted that he had many peculiarities, they stoutly maintained that he was a man.”

Paolo Rinaldi, a barber, told the reporter that De Raylan had been extremely anxious to grow a mustache. Rinaldi said that his customer had used at least 20 lotions and creams in an effort to get his facial hair to grow, and applied one, made of wine and water, 10 times a day. The barber went on to say that, on his advice, De Raylan had taken to shaving four times a day, apparently under the assumption that this would stimulate the follicles. De Raylan stuck with the task for two months, according to Rinaldi, “but at no time was there the faintest sign of hair upon his face.”

In a similar vein, a cabdriver named S.D. Lambrakis told the Inter Ocean that De Raylan “on numerous occasions” went out in women’s attire. On other occasions, the driver watched as De Raylan and a female companion fought in his cab. “It was De Raylan’s favorite diversion to scratch the face of his companion. He never resorted to blows,” Lambrakis said, insinuating that De Raylan fought like the woman he was later discovered to be.

And yet, the reporter noted, “De Raylan’s habits … were those of the ‘rounder.’ Chorus girls, wine suppers and ‘red light’ tours were a part of his regular routine. All intimates of the dead secretary agreed that he smoked and drank in excess. He was never without a cigarette and he was able to drink some of his stoutest companions ‘under the table.’ ”

Edward Burchulis, who had married De Raylan’s ex-wife, Eugenia, remarked incredulously, “Why, I have been swimming with him, both at Atlantic City and in the Central YMCA here in Chicago. I am sure he was a man.” (One can only assume De Raylan was wearing a bathing suit that covered his top as well as his bottom.) Even Baron von Schlippenbach, who’d worked daily with De Raylan at the Russian consulate, claimed to have had no inkling that his private secretary had a female body. “He professed to be astounded by the statements of the coroner at Phoenix,” the Inter Ocean reported, and “refused to explain how a man without proper credentials could be advanced to so important a post as that enjoyed by De Raylan.” As for Rowe, the doctor said he’d examined his now-famous patient many times—presumably without asking him to undress fully—and never found anything unusual.

Other posthumous accounts of De Raylan’s public life were riddled with similar contradictions. In some, acquaintances recalled him wearing clothes that hid the curves of his body. In others, he was described as a family man pulling down a handsome salary and engaging in virile activities like horseback riding with the Hussars, a volunteer regiment of gentlemen equestrians. He’d even boasted (falsely, in all likelihood) of having served in the Russian army and the Spanish-American War.

The details of De Raylan’s earlier life didn’t begin to come to light until several months after his death, when a law clerk handling the deceased’s modest estate discovered his personal journal, had it translated from Russian, and discussed it with reporters. From a series of newspaper articles based on the journal—along with legal documents and historical records unearthed in recent years by University of Illinois at Chicago professor Jennifer Brier and two graduate students—a curious story emerges. It’s one that both unlocks and deepens the central mystery of De Raylan’s life.

Nicolai Constantinovich De Raylan was born Anna Terletsky around 1873 and grew up in Kiev, the capital of what is now Ukraine. Raised in a convent by a French governess, Anna didn’t know her father, though she suspected that he was a member of the Russian nobility. Sometime in the 1880s, Anna, with the help of her governess, decided to seek a share of the considerable fortune possessed by her mother, Seraphima Terletsky. In order to strengthen her claim as a rightful heir, Anna intended to tell authorities that she was actually a boy who had been raised, illegally, as a girl by her mother. Thus began, according to the account in De Raylan’s journal, Anna’s journey into manhood.

In a letter, Anna’s governess beseeched a high church official named Constantin Petrovich Pobedonostsev, procurator of the Holy Synod and an adviser to Czar Alexander III, to hear Anna’s case. Anna was granted a private audience with the procurator at the imperial palace in St. Petersburg. During the interview, Pobedonostsev became so confident that the young person before him was male that he agreed to testify to that effect at a trial that would adjudicate Anna’s claim on the family fortune.

The young Terletsky didn’t stick around to find out what happened in court. Facing the possibility of having to undergo a medical exam—which might reveal her secret and surely spur the vengeance of the procurator, who’d put his credibility on the line for her—she fled Russia, first for Finland and then, after an unspecified amount of time, for Belgium.

Terletsky continued to maintain a male identity after leaving Russia, and very successfully at that, according to the journal, which describes an encounter with a boat captain who suspects Terletsky is female but is convinced otherwise in a “secret interview.” (What precisely transpired in that interview isn’t revealed.) By the time Terletsky had settled in Belgium, she had fully abandoned her female identity, having landed a job working for a banker. The banker held Terletsky in high enough esteem that he eventually sent the man—for that is what Terletsky now was, by all outward measures—on an errand to America. That is where the Russian émigré would ultimately stay, living for a time on the East Coast and moving to Chicago around the time of the 1893 World’s Columbian Exposition.

When exactly did Terletsky adopt the ­aristocratic-sounding name by which she’d later be known? When did she begin wearing the chamois penis? How were so many people so firmly convinced, even after close encounters, that Terletsky was male? And why did this mysterious Russian continue to pose as a man well after escaping the reach of the czar’s secret police? The answers remain elusive, though with regard to the last question, it’s safe to say that more was at play than a desire for financial gain. Indeed, De Raylan’s journal hints that the young Terletsky and her governess had been romantically involved, and it notes that she fled Russia using money borrowed from an amorous conquest referred to as the “little St. Petersburg sweetheart.”

On top of that, says Jennifer Brier, who included parts of De Raylan’s story in a 2012 book she coedited called Out in Chicago: LGBT History at the Crossroads, “it would have been much easier to get across the ocean and to get around in the streets of Chicago as a Russian man than as a Russian woman alone.” It would be shortsighted, Brier says, to see the invention of De Raylan’s male persona “as an effort to deceive, as a life rooted in deception.” Brier sees him more as “a female-bodied person exercising body autonomy”—that is, a transgender person presenting as male—in an Old World society that defined sex roles very narrowly.

And of what of Chicago during that era? Certainly, people were more strait-laced about sex and gender than they are today, but maybe not to the extent that one might think. De Raylan arrived in Chicago when it was booming. The city was a bustling crucible of new inventions—the zipper, the Ferris wheel, spray paint—and a magnet for those who wanted to reinvent themselves.

Sitting at the crossroads of America, with rail lines delivering thousands of people from small towns filled with prying eyes, Chicago was a place where boundaries could be breached, and many transgressors found themselves at home here. Among them: Henry Blake Fuller, the son of a wealthy family who wrote a play in 1896 and a novel in 1919 that were among the first open depictions of homosexual relationships in their respective genres. In 1899, Omaha brothel owners Minna and Ada Everleigh moved to Chicago and, a year later, opened the Everleigh Club, which quickly became one of the nation’s best-known prostitution parlors, with a roster of customers that included Marshall Field Jr. and Prince Henry of Prussia. At a club called the Sappho, possibly the city’s first lesbian establishment, patrons of the nearby brothels came to watch girl-on-girl-themed shows.

What’s more, transgender people were hardly unheard of when De Raylan arrived in the city. Probably at least a few Chicagoans had read about Frank Dubois, a Wisconsin man who was discovered to have been born a woman after a former spouse and two children traveled from Dubois’s hometown of Belvidere, Illinois, to confront him. Another Midwesterner, Jennie Hodgers, changed her name to Albert Cashier at age 19 and passed successfully as a man in order to fight in the Civil War with the 95th Illinois Infantry. (Hodgers had also lived in Belvidere, almost certainly making it the only small town of that era that had been home to two documented trans people.) Another famous trans contemporary of De Raylan’s was Harry Allen, a petty crook from the Seattle area who’d been born Nell Pickerell and talked openly to the press about his refusal to wear dresses and other feminine accoutrements.

Still, the growing acceptance and understanding that transgender people now enjoy was mostly nonexistent in the Chicago of De Raylan’s time—one psychiatric journal of the day referred to him as “an android woman, homosexually conjugally mated to a woman”—and the work of keeping his female anatomy secret must have been exhausting.

By all appearances De Raylan embodied wholeheartedly the conventional attributes of the men of his era—for better or, sometimes, worse. The divorce complaint filed by his first wife, Eugenia, in Cook County Circuit Court in June 1903 contended that De Raylan “has been guilty of extreme and repeated cruelty.” Such a claim wasn’t unusual in a divorce petition, but the level of detail gives pause: The complaint tells of beating, pinching, choking, kicking, and the use of “vile, abusive and opprobrious language.” It also contends that on July 4, 1899, De Raylan came home drunk and punched Eugenia while she was nursing a baby (it doesn’t say whose) and that he poked her with a sword, making “several wounds on [Eugenia’s] body in attempting to kill or do great bodily injury.”

We don’t know if De Raylan’s second marriage, to Anna Davidson, an actress who had a 10-year-old son, was equally tumultuous. Whatever the case, the accounts of both relationships do little to answer the questions that are foremost in 21st-century minds: What exactly were the wives getting out of this sexually, and to what extent were they in on De Raylan’s secret? There’s no record of whether his first wife believed she was married to a man with a penis, a man with a vagina, or simply a woman with a vagina and a man’s wardrobe.

De Raylan’s second wife adamantly claimed to the Inter Ocean that the reports coming out of Phoenix about her husband’s body were preposterous. “They must have substituted some other body for my husband’s,” she told a reporter. “This terrible mistake must be cleared up, and I am going to see that it is done.” Subsequent news items reported that De Raylan’s widow and her son traveled by train to Phoenix, where she requested that the body be dug up. A second examination was conducted, but it merely confirmed the results of the first.

Were Anna’s protestations genuine? Some newspaper reports suggest they weren’t, contending that Anna not only knew of De Raylan’s birth sex but had also attempted to blackmail him with the secret, and thus was only feigning indignation after his death in order to preserve her inheritance. Still, the possibility that she really believed she’d been married to a man can’t be dismissed. “I’m sure some of De Raylan’s partners didn’t know what the hell was going on, or didn’t know what to expect to feel in a dark bedroom,” says Ramón Gutiérrez, a professor of American history at the University of Chicago who has written on the history of sexuality. “They probably didn’t know what a penis looks like or how it’s used—I mean, there are men and women in the 21st century who don’t know how to use a penis—but as long as they were being satisfied, it didn’t matter.”

In the end, what little remained of Nicolai De Raylan’s painstakingly maintained identity as a man was dismantled by two material things he left behind: his money and his body.

An undated record from Cook County Probate Court confirms that Anna received not a penny of her late husband’s estate, which amounted to about $87,500 in today’s money. The revelation about her husband had evidently rendered her marriage null and void in the eyes of the court. Who did inherit the money? After paying off claims submitted by a storage company, an ice company, and a few of De Raylan’s associates, the court-appointed administrator awarded a sum of $3,124—the equivalent of about $81,000 today—to none other than Seraphima Terletsky, “mother of Nicolai de Raylan [and] sole heir.”

If this outcome caused De Raylan to turn over in his grave, he did not do so attired as he would have liked. “At first there was a feeling that her wishes in life should be respected in death,” the Daily Review of Bisbee, Arizona, reported the day after the burial, using feminine pronouns to refer to the deceased. “It was planned that she be buried garbed in the long Prince Albert coat and the dark trousers which had been her favorite costume in the part she took. But other counsel prevailed and the woman went to her grave in a long silk robe of white—a soft, dainty, womanly garment in which one wondered how De Raylan was ever taken for a man.”