3. Criminal Perverts, 1910–20

The official declaration that Brooklyn and Manhattan were now one city had far-reaching and slow-moving consequences, as two of America’s foremost metropolitan centers worked to knit their civic institutions together. So it was that the Brooklyn City Prison—generally known as the Raymond Street Jail—wasn’t turned over to the new New York City Department of Correction until 1908, a full decade after the cities were joined. When it was built in 1838, at the corner of Willoughby and Raymond Streets (in the area known today as Fort Greene), the prison was a declaration of Brooklyn’s aspirations to greatness, writ in limestone and human misery. Modeled after the Bastille in Paris, it was built to imprison upward of four hundred people at a time. One famous—and likely apocryphal—story holds that when the jail was constructed, the builders forgot to include a front door; an apt metaphor for the way prisoners were treated. A women’s auxiliary, known as the Annex, which held around forty people, was added the next year.

When the jail was built, there wasn’t much to the neighborhood, which was nestled between downtown Brooklyn and the lightly unsettled area where the town of Weeksville would soon be. There had been a Revolutionary War–era fort, but it was decommissioned in 1815. Prominent Brooklynites, including the editor of The Brooklyn Daily Eagle (the still unknown Walter Whitman), pushed for the land to be turned into Brooklyn’s first official park. In 1848, thirty acres were designated for that purpose. The jail and the new Washington Park (known today as Fort Greene Park) were separated by just a single block of empty land. The small residential part of the neighborhood was mostly laborers who worked in shipbuilding, predominantly at the Navy Yard. By the end of the nineteenth century, the area was home to about half of Brooklyn’s small black population (as is still true today, correctional facilities are much more likely to be found in black neighborhoods than in white ones). With every year, Brooklyn stretched farther to the east, incorporating large farms and small towns as it went. By the early 1900s, the areas of Bedford, East New York, Crown Heights, and Flatbush would all be growing Brooklyn neighborhoods.

Not much changed at the Raymond Street Jail over this first seventy years of its existence. The small exercise yard was surrounded by thick stone walls some twenty-four feet high, and four iron gates stood between the imprisoned men and the outside world (five, if you counted the one on their cells). Inside, the men were kept in a long open room, which had two rows of metal cages stacked four high. When it was taken over by the Department of Correction in 1908, inspectors said:

Males were confined in dark, smelling cells with no light whatever, except that furnished from a flicker of a candle, a luxury to be enjoyed by those who had the means to procure this and at an exorbitant price. The odor arising from the cells was almost unbearable.¹

This was because the city refused to spend money on cleaning services. As the prisoners held at the Raymond Street Jail were all awaiting trial (a period that could last up to six months), they were technically considered innocent, which meant the Department of Correction couldn’t compel them into forced prison-labor cleaning crews. As a result, the men’s jail was perennially filthy.

The women’s Annex was cleaner and brighter, with the women kept in separate rooms off central hallways, but it was “above all a wretched fire trap.”² Conditions were so bad that when the NYC Department of Correction took over, they immediately tore down and rebuilt it, while they merely renovated the men’s jail. Although these changes made some improvements (for instance, making it harder for imprisoned people to commit suicide by jumping off the roof), postrenovation the men’s jail was still condemned as a dank, dreadful place where prisoners spent the entire night in darkness, leaning against the bars to catch a glimmer of lantern light from the guards’ rooms. By 1911, some twenty thousand men passed through its cramped metal cages every year.³ Smuggled drugs, particularly heroin and cocaine, were a constant problem. Still, newspapers argued, this was an improvement over how it had been in the past, when it was “dirty, ill managed, the prisoners were starved, [and] it was dark and filthy and worse than anything in Siberia.”⁴ As for the women’s prison, cleaner didn’t necessarily mean safer or more compassionate. A 1904 newspaper report strongly suggested that two of the guards had sexually assaulted an imprisoned woman in one of the bathrooms.⁵ In 1909, a report by the Women’s Prison Association complained that “insane women are turned loose in the corridors,” even though magistrates now had the option to send them to charity institutions instead.⁶ Concern for the delicacy of womanhood, it seems, ended where the doors of the jail began.

Although prisons are rarely considered a queer space—except in the context of disturbing jokes about sexual assault—they are as intimately connected with queer people as any other physical locations in American history, particularly in the twentieth century. Queer people were sent to jail for specifically queer crimes (such as cross-dressing and sodomy), and queer people picked up on other charges were often given lengthier sentences because of their sexuality or gender presentation. Imprisoned queer people lived under constant surveillance, making it more likely that straight people (from doctors to wardens to other imprisoned people) would notice their existence. And like all other single-sex institutions, jails provided space for people to explore same-sex desires that they might never have recognized or had the chance to engage with in the outside world. Thus, in the first decades of the twentieth century, as doctors, lawmakers, and moral reform organizations began to explicitly focus on sexuality, prisons such as the Raymond Street Jail would become queerer and queerer spaces. And in the year 1910, a shocking trial would see two Brooklyn men held in the jail for months on charges of obscenity, sodomy, and first-degree murder.

It all began when seventeen-year-old James Vickers landed in New York City in the waning days of December 1909. At the age of fourteen, Vickers had left his home in Philadelphia to work for three years as a fireman on an ocean freighter, and he hoped to find similar work in the docks of Brooklyn. The blue-eyed, brown-haired Vickers was short but powerfully built, standing just five feet tall and weighing 150 pounds. For a little while, he found a place to stay in the Bowery, a notorious slum in lower Manhattan. Around Christmas Day, he wrote his mother and stepfather with the exciting news that he “had fallen in with two men in Brooklyn who were going to give him a good home.”⁷ Those men were James Hagaman, a painter of some small renown who lived in Brooklyn Heights, and the architect Emerson Colburn, who lived in the area of Brooklyn known as East New York, a growing residential neighborhood to the east of what had once been Weeksville (which had now been rebranded as suburban Crown Heights). Around this time, despite a warning from his stepfather to be “extremely careful about the friends he had made in New York,” Vickers moved in with Colburn.⁸ On New Year’s Day, he was found raped and murdered, his naked body sprawled on a divan in Colburn’s spare room.

Hagaman and Colburn were quickly arrested and charged with sodomy and first-degree murder. The pair claimed they had discovered Vickers unconscious and called a doctor, but he died before the physician arrived. Evidence against them mounted swiftly, however: a coroner testified that the boy had been dead for at least three hours before the doctor was called; Colburn had a black eye, which he first claimed was from boxing, but then admitted had come from Vickers; and the two seemed generally incapable of keeping their stories straight, each claiming they had last seen Vickers at different times on different days. Within a few weeks, it would come to light that Colburn had previously sexually assaulted a fifteen-year-old Brooklyn boy in 1904. The final nail in his coffin appears to have been the discovery of obscene photos, made by Hagaman, in Colburn’s home, along with a list of the names and addresses of some two hundred other sailors. Presumably these were men they’d also met along Brooklyn’s waterfront, like Vickers.

Obscenity charges were a big deal at the time and were frequently used against makers of pornography, publishers of “indecent” novels, sexual-health educators, people who performed abortions, theaters, and—increasingly—anyone looking to provide the general public with information on queer people. The most powerful censor in the country was Brooklyn postal inspector Anthony Comstock, who successfully lobbied Congress to pass in 1873 a law banning the shipping of “obscene, lewd, or lascivious” materials through the mail. This law was one of those most frequently used against queer people, along with sodomy, masquerade, and disorderly conduct charges. Under the auspices of his organization, the New York Society for the Suppression of Vice, Comstock wielded obscenity charges like a weapon against those he viewed as moral degenerates. It’s not unlikely that he or one of his acolytes had a hand in the Vickers case.

Faced with an additional felony obscenity charge (on which he would almost certainly be found guilty), Hagaman quickly turned against Colburn, who was convicted of sodomy and murder in the first degree. Colburn was sentenced to sixteen years in jail, and in exchange for his testimony, Hagaman received a light sentence of eleven months in the workhouse.

The case of James Vickers represents a transitional moment in our understanding of sodomy. Sodomy has come to be synonymous with consensual sex between men, but for most of American history, it was a broad concept that contained many kinds of nonprocreative sexual activity, performed by both men and women. Before World War II, the legal charge of sodomy was one step removed from rape, and “prosecutions were generally against aggressive men deriving sexual pleasure from a weaker person, usually a boy, girl, woman, animal, or ward.”⁹ Starting in the time of Young Griffo, the boxer, sodomy prosecutions became more common in New York City because of the work of the Society for the Prevention of Cruelty to Children (SPCC). Often referred to just as “the Cruelty,” for their habit of taking children away from working-class parents for relatively minor infractions, the SPCC breathed new life into New York’s antisodomy laws by using them to prosecute adult men who abused male children. As George Chauncey documented, there were twenty-two sodomy prosecutions in New York City between 1796 and 1873, but starting in the 1880s, “the number of prosecutions increased dramatically … [and] at least 40 percent—and up to 90 percent—of the cases prosecuted each year were initiated at the complaint of the SPCC.”¹⁰ This was fully in keeping with earlier uses of the law as an anti-sexual-assault measure, but by focusing only on male-male sexual assaults (and not male-female assaults that didn’t involve vaginal penetration, bestiality, etc.), they would help to redefine sodomy, in the eyes of the public, as synonymous with homosexuality—and homosexuality as synonymous with pedophilia.

As was true with Young Griffo, neither Colburn nor Hagaman were ever identified as “homosexuals” or even “fairies” in newspapers or court reports. However, the court repeatedly referred to Vickers as a “catamite,” a Renaissance term for the younger, passive partner in a sexual relationship.¹¹ This suggests that even in a case of rape, being penetrated could compromise a man’s heterosexuality, while an act of sexual assault—even against another man—might not. Broadly, the court was more interested in Hagaman’s and Colburn’s other sexual crimes than their sexual identities, because in as much as the courts were interested in sex, it was as a form of violence. Over the 1910s, however, a triumvirate of powerful forces would work together to punish and control consensual same-sex and cross-gender desires. Sodomy prosecutions would continue, but more and more of them would target consensual sex between men, and proportionally fewer would focus on sexually violent cases like that of Emerson Colburn and James Hagaman. Medical professionals, legal experts, and civilian reformers would begin to make the case that queerness was directly linked with criminality and mental illness; that existing legal tools were inefficient or ill-suited to prosecuting criminal identities (as opposed to criminal acts); and that the entire future of the “white race” was imperiled by creeping hordes of black people and queers.

While the motives and conclusions of these doctors, lawmakers, and antivice organizers are biased and often self-serving, their work provides a vast (if problematic) archive of information about queer people in America at the start of the twentieth century. Many of these investigators published their results in medical journals or were connected to powerful institutions that generated reams of forms, annual reports, and internal memos. These, in turn, made their way into growing civic institutions, such as libraries and municipal archives, which preserved them for future study. This is yet another way in which urbanization helped to make queer lives visible to future generations.

Before turning to these records, it is important to consider a few things. First, this information reflects only those queer people who came to the attention of these more powerful groups, not all queer people. Second, these sources are not neutral records of events as they happened; rather, they were created by people who were already actively invested in containing and controlling queer desires. Finally, it shouldn’t be assumed that just because queer people were participating in these interactions that they were necessarily telling the truth. Even in situations that weren’t clearly coercive, such as a patient talking freely to a doctor, queer people might, for many reasons, have shaded or dispensed with the truth entirely. Part of the difficult work of researching queer history is balancing this asymmetrical record, and paying attention to what queer people said and did, not just what was said and done to them. Many of these records might best be understood as recordings of what straight people knew, thought, assumed, or did about queer people, rather than being directly about queer lives.

Despite these caveats, these kinds of documents are an incomparable resource to historians of sexuality. They contain information that would otherwise have gone completely unrecorded—such as the earliest record of an explicitly transgender person in Brooklyn, a sex worker who went by the name Loop-the-Loop.

Loop-the-Loop was a young white trans woman from “the slums of Brooklyn,” who was born on April 23, 1883 (just a few months before the death of the Great Ricardo). She was tall for her day—five feet eight inches—and slender, with wavy dark brown hair that she often tucked under a blond wig. Her eyes were blue, her teeth bright white, and when she was fourteen (in 1897), she’d had her ears pierced. She’d adopted her name from the popular Coney Island roller coaster, which had opened in 1901 and was one of the first to turn its riders completely upside down. She was an orphan, and she lived with a woman who acted as her guardian. Quick-witted, perceptive, and talkative, she had a meager education; though she could read English, she couldn’t write it well.¹²

Photograph of Loop-the-Loop (c.1917), taken by Dr. R. W. Shufeldt and published in the American Journal of Urology and Sexology. (Photo courtesy of the New York Academy of Medicine Library.)

How then do we know so much about Loop? On multiple instances, starting in 1906 and continuing at least until 1916, she was examined by Dr. Robert Wilson Shufeldt, who would publish his interactions with her in a 1917 journal article entitled “The Biography of a Passive Pederast.”

As well as being a medical doctor, Shufeldt was an army lieutenant, prolific author, passenger pigeon enthusiast, photographer, grave robber, sexologist, blackmailer, and virulent racist who believed that inversion and miscegenation were leading America to white racial suicide. He saw his work on sexuality as a means of saving humanity, and in particular saving the white race from a slow, etiolated death by attrition. When Shufeldt wasn’t writing about “passive pederasts” such as Loop, he devoted his time to publishing books with titles such as America’s Greatest Problem: The Negro and The Negro: A Menace to American Civilization. However, these weren’t two separate topics that caught his interest; rather, they were both part of his belief in the science of eugenics.

Early twentieth-century medical science was dominated by the eugenics movement, which believed social problems were rooted in deviant bodies and inheritable traits. This movement reached its apogee with the sadistic, anti-Semitic science of the Holocaust, which has allowed us to conveniently forget the power and prevalence of the eugenics movement in America. Just as people of color, women, and queer people were gaining social power and becoming visible, eugenic science would be trotted out to prove that black people were less human, women were less intelligent, and queer people were a biological dead end that threatened to contaminate good (white) Americans. The same doctors who would define “the homosexual” as a biological class unto itself would also define “the pickpocket” that way, and “the woman who is erotically stimulated by hat pins” as well. Today, it seems natural to view homosexuality this way, and ridiculous to think that being a pickpocket might be a hereditary, biologically defined class. But this is the biased, thoroughly unscientific swamp from which our modern ideas about sexuality arose.

As a eugenicist, Shufeldt’s interest in Loop was twofold. One, Shufeldt wanted to define what it meant to be a “contrary sexed male,” primarily in terms of Loop’s physiology, but also to some degree in terms of her lifestyle. Two, Shufeldt wanted to show that her degeneracy could be read from, and was defined by, her body. Sigmund Freud’s system of psychoanalysis, and his ideas about sexuality residing in the human mind, only reached American shores in 1909. It would take long decades before they would supplant eugenic ideas about the body as our dominant way of understanding sexuality (and personality in general). For this reason, Shufeldt’s article, although ten pages long, barely contains any insights into what Loop thought or how she was raised. But it does meticulously diagram her body, including multiple nude photos. Loop’s body, not her mind, was where her problems lay.

A surprisingly large number of body parts could communicate unwholesome or downright psychopathic personality traits, according to Shufeldt. Loop’s facial features were “coarse” and “of a criminal cast.” Her “thin, non-sensuous lips” were inconclusive, but suggested she was more of a decisive kind of person than a weak one. Overall, Shufeldt judged that her face lacked “every expression indicative of truth, refinement, or good moral purpose.” Although Loop informed the doctor that she had breasts, Shufeldt said he could see no evidence of gynocomastia, the technical term for the development of breasts in someone who was judged to be male at birth. This was a good thing for Loop, Shufeldt believed, as gynocomastia “is in evidence sometimes in criminals.” Tellingly, although she could sing soprano, Loop could not whistle—a deficit that was at the time a commonly accepted indicator of inversion. Overall, Shufeldt judged her to be a “nervous, loquacious, foul-mouthed and foul-minded ‘fairy’ of the most degraded slums of a multi-millioned city.”¹³

Loop made her living as a sex worker, and more specifically, as a streetwalker in Brooklyn. Digest this thought and all it implies for a moment: as early as 1906, in some areas of Brooklyn a trans woman could be out on the street, soliciting for sex, with an active clientele. When Shufeldt pressed her about how these men reacted to such things as her body hair, Loop simply shrugged and said, “Most of the boys don’t mind it.”

According to her own statements, Loop was sexually aggressive and had a high libido. She seemed to delight in telling Shufeldt outlandish stories from her sexual exploits, which began at least by the age of sixteen (in 1899), when she was “constantly in the company of men whom [she] sought as paramours.” You can almost hear the good doctor’s virtuous panic when he wrote:

[She] informed me that on one occasion [she] had satisfied as many as forty men in twenty-four hours, and that on the 21^st of July, 1906, no fewer than twenty-three men copulated with [her] (immissio penis in anum), one immediately after the other, each producing ejaculation during the act; this took place in a room in Brooklyn.

During their last meeting before Shufeldt wrote his article, Loop brought along her boyfriend of several years, a musician whom Shufeldt described as “an intelligent young man, of about twenty-four years of age.” Shufeldt seemed disinterested in him, aside from being slightly shocked that he was so “cool, collected, and respectful.” This was most likely because Shufeldt judged him to be heterosexual (but seduced or tricked by Loop), or at most an “acquired invert,” whose body was likely to lack the usual tells that Shufeldt was looking for in a “congenital invert” such as Loop.

Acquired inverts, in this developing schema of sexuality, were those who mostly conformed to traditional gender roles. Their attraction to members of the same sex was assumed to be brought on by a lack of appropriate sex objects, coerced by a congenital invert, or was a sign of their utter dissolution and/or insanity. (Josie Mansfield, the lover of Ella Wesner, would have been seen as an acquired invert.) Because acquired inverts did not fit well into an understanding of sexuality that rested on gender and visible bodily signs of inversion, eugenicists tended to ignore these men and women. Shufeldt was willing to accept that some normal-seeming men might, after drinking, have sex with a woman such as Loop, but for a nice young lad to talk openly about a relationship with such a person was disarming. Even as doctors such as Shufeldt were laying the groundwork for our modern idea of homosexuality, they couldn’t see it themselves. Had Shufeldt investigated the young man with the thoroughness with which he examined Loop, he might well have been forced to confront the biased limitations of his science—and so he didn’t.

What incensed Shufeldt most about Loop was not her body or her sex life, but rather, her complete openness about being who she was. “Lost to every sense of shame,” Shufeldt wrote, Loop answered his invasive questioning “as though [she] were talking about the rearing of fancy pigeons.”

Loop told Shufeldt that she was, in our modern terms, intersex (meaning her body had a mixture of typically male and female characteristics), and that she had previously been pregnant. Shufeldt disputed this with his medical examinations, which were so thorough they bordered on being a cavity search. It’s impossible to know what to make of Loop’s assertions. Did she truly believe herself to be intersex? Was this an elaborate camp put on by a fairy out to have some fun with a serious doctor? Or was she attempting to tell Shufeldt what she thought he wanted to hear, to get him to validate her identity (as many trans people are still forced to do with therapists and doctors today)? The answers to these questions remain unknowable, but the questions are important to highlight because we have no insight into them from Loop’s point of view. She had her own motivations for allowing herself to be studied and may not have been entirely truthful with Shufeldt.

Aside from her claim to be intersex, in only one other matter did Shufeldt question Loop’s story: when she told him that she had never been arrested—“something I am very much inclined to doubt,” he noted in his article. Loop pushed back and offered to give Shufeldt a nighttime tour of the Brooklyn streets where she worked. “Fifty cents or a dollar will buy off any cop,” she told him, “and that from dark to daylight. We all do it.”

How tantalizing are those last four words—who is the we? Aside from bribing the cops, what exactly did they all do, where did they do it, whom did they do it with, and how many of them were there? These questions either went unasked, or Shufeldt deemed the answers not worth recording.

However, Loop was not the only trans person in New York who came under Shufeldt’s microscope. In 1918, a year after he wrote about Loop, his photographs of a trans woman named Jennie June were published in the book Autobiography of an Androgyne. This book was the first in a three-volume biographical series written by June, who obscured the facts of her life so well that to this day no historian has been able to identify her. Unlike Loop, June was highly educated and had access to both wealth and doctors on a more even footing. Much like Ruth Fuller Field, June wanted to share her story with sexologists (and eventually laypeople) to promote a greater understanding of inversion. Her first volume was completed around 1899, but it took her nearly twenty years to find a willing publisher—primarily because of anti-obscenity crusader Anthony Comstock. According to June, upon being given a copy of her book, Comstock told her that he would never allow it to be widely distributed. To get around him, Autobiography of an Androgyne was offered for sale via the Medico-Legal Journal, with a note stating it was “sold only to physicians, lawyers, legislators, psychologists, and sociologists.” Queerness was now the provenance of powerful men.

Autobiography of an Androgyne reveals a wide world of “fairies” having sexual relationships with men, mostly working-class white men who both accepted Jennie June as a trans woman and also frequently resorted to violence, extortion, and blackmail against her. In the first chapter, she offers an interesting etymology of the word fairy:

It probably originated on sailing vessels of olden times when voyages often lasted for months. While the crew was either actually or prospectively suffering acutely from the absence of the female of the species, one of their number would unexpectedly betray an inclination to supply her place. Looked upon as a fairy gift or godsend, such individual would be referred to as “the fairy.” ¹⁴

It’s impossible to know how apocryphal this story is, but it again highlights the connection between sailors and queer sexuality, as well as a kind of male sexual flexibility whose existence is routinely denied today.

June met men mostly in saloons and on the streets in less reputable areas of Manhattan, including the Bowery and (as she calls it) the “14th Street rialto,” which is today the area near Union Square. She also frequented nearby military forts, which she referred to as being “outside the city,” but by which she probably meant in the outer boroughs. June mentions both College Point and Whitestone in Queens, but sadly, whether she ventured out to Brooklyn is impossible to say. However, the larger worlds in which both she and Loop moved were likely fairly similar and overlapping. Although June came from an upper-middle-class background and knew some other inverts of her own social strata, most of her public life as a fairy was spent in working-class areas, much like the “slums of Brooklyn” where Loop lived and worked. June’s books provide rare, first-person insight into how trans women were received in these spaces. Here, for instance, is her reminiscence of a typical night spent at an at-home tenement party:

With half a score of adolescents and two or three young women, an evening would be spent in some humble two-room apartment. Everybody was exceedingly happy, and I perhaps the happiest of all, sitting now in one young man’s lap, and now in that of another. And how we all did sing! The young men petted and babied me more than they did any of the girls, and even right before the eyes of the girls. The latter were not jealous of me, especially because I was the one who financed these parties.… The girls thought nothing strange of me, as the nature of fairies was well known to them. I wish it understood, however, that these gatherings were no more indecent than a children’s party in the best social stratum. Even these knights of Mulberry Street had their sense of decency. At these home parties, extreme intimacies were allowed only in private. The only refreshment was beer, the three-quart pail passing around the room from mouth to mouth, and being repeatedly sent out to be refilled.

June estimated that two-thirds of the young men in these neighborhoods would, under the proper conditions, be attracted to a woman such as her. Most of the men with whom June had relationships did not seem to think that their own identities were threatened or changed in any way by desiring her. She might not have been the kind of woman they were used to, but she was a woman, and they were men, and so the natural order of gender went undisturbed in their eyes. Today, we function on something of a “one-drop rule” when it comes to male sexuality: any amount of sexual experience with or attraction to another man, or to a gender-nonconforming person, defines you as being queer. But in the early 1900s, that was far from a settled way of thinking. In Gay New York, George Chauncey characterizes the place of fairies in working-class cultures in New York as being similar to that reserved for sex workers (perhaps in part this is because both fairies and sex workers first came to popular attention inside the same bawdy saloons). This identification afforded them an understandable role in the community: “The fairy’s sexual aggressiveness in [her] solicitation of men was certainly inconsistent with the sexual passivity expected of a respectable woman, but it was entirely in keeping with the sexual character ascribed to tough girls and prostitutes.”¹⁵ This connection between brassy women and fairies would be celebrated in the 1910s by such performers as the Brooklyn-born Mae West, whose stage persona was said to be inspired by popular vaudeville drag queens such as Bert Savoy and Julian Eltinge—another way in which the theater, sex work, and queer identity have always been interrelated.

However, the fact that queer people occupied this place in working-class culture allowed upper-class sexologists and reformers to dismiss them as inherently degraded. June wrote her book so that the experts in her readership would be “moved to say a kind word for any of the despised and oppressed step-children of Nature—the sexually abnormal by birth.” But her life story would also be used to vilify queer people of all kinds, particularly the men who had sex with her.

June got her book sold by having it prefaced, edited, and verified by Dr. Alfred W. Herzog, the publisher of the Medico-Legal Journal. Despite finding the book “nauseating,” and believing it lacked “any scientific value,” Herzog agreed to publish it largely unedited as a kind of exposé of the one of dark corners of modern life.¹⁶ He seemed to genuinely pity June and to have some general sympathy for the people we would today define as transgender. But it was a complicated, patronizing kind of sympathy.

In his introduction, Herzog perfectly captured the shifting (and shifty) understanding of queerness that was emerging in the 1910s. He explained to his readers that “if a male feels sexual desire for another male, or a female for another female, they are called sexually inverted or homosexual.” He mentioned Freud’s theory that all people are born bisexual, but contended (with no explanation) that this condition was established “anatomically,” not just psychologically. He laid out three possible routes to adult inversion: the born invert such as Jennie June, who was both transgender and intersex; the acquired invert, who is inducted into inversion in childhood (again, connecting adult homosexuality with pedophilia); and finally, a kind of indiscriminate or forced inversion that is caused by a normal man’s being full of vice and sensuality (and possibly insanity) that has no outlet. From this standpoint, Herzog argued for a complicated legal approach to queerness, which basically was to allow trans women such as Jennie June to live freely, because it was their nature, but to work to prevent or punish all other forms of queerness. He ends his disquisition on a muddied note, showing just how unclear all of these identities were, even to so-called experts such as Herzog. Going back on his definition of the homosexual quoted above, he wrote that a trans woman such as Jennie June “is a homosexualist, because he feels like a woman and to him all male persons belong to the opposite sex.… He is born an androgyne … a male person with female ways.”

Herzog’s introduction marks an intermediate point in our understanding of queerness, one that’s not yet our modern ideas of sexuality and gender identity, but gestures in those directions. We can see that Herzog had begun to locate sexuality in the mind as well as in the body, and to separate homosexuality from being transgender—sort of.

A trans woman such as June made sense to Herzog: she desired men, acted in a feminine manner, and even had parts of her body that Herzog decreed to be more female than male. But masculine men who desired other men or trans women such as June were a strange and dangerous hybrid of gendered impulses. In Herzog’s eyes, this made them either crazy or utterly debauched and immoral. Sexuality was still understood as a function of gender, and at least June wanted to have an appropriate gender identity: feminine, attracted to men, and with an acceptably female body. But the masculine working-class men who wanted June not only broke those rules, they seemed entirely unconcerned with them. In this, Autobiography of an Androgyne highlights a fascinating disjunction in early American understandings of queerness: June’s manly working-class lovers saw themselves as sexually normal, whereas her upper-class doctors saw their desires as not only abnormal, but downright dangerous to the fabric of society.

June herself mostly agreed with the classifications laid out by Herzog (if not the antipathy that animated them), but with one main point of differentiation: instead of seeing herself as “a male person with female ways,” June defined inverts such as herself as having a “female brain in a female body” that had “various abnormal developments along the line of male structure.” Like Loop-the-Loop, June actively pushed back against the scientists who were seeking to define her existence, even while she cooperated with them.

Transgender men from this period wrote no comparable documents; however, the prosecution of one Elizabeth Trondle for “masquerading in men’s clothes” in 1913 captured Brooklyn’s imagination and made headlines across the country. Cross-dressing arrests were not uncommon in this period, but Trondle’s outspoken and unrepentant thoughts on gender were so outlandish that newspapers across the country quoted them at length, allowing us some unique access to his thoughts.

Trondle’s brief time as a cause célèbre began when he was arrested in the back room of a saloon while “masquerading in male attire, smoking cigarettes, and drinking with men.”¹⁷ Like James Hagaman and Emerson Colburn, he was confined at the Raymond Street Jail while on trial, and his case was heard in the courthouse on Adams Street, which was located just a few blocks from where Mary Hallock Foote once lived in Brooklyn Heights.

Trondle claimed to be twenty-four, and an orphan, but a court probation officer asserted that he was seventeen and had family in the Richmond Hill neighborhood of Queens. Apparently, this was not the first time he’d been in trouble with the judicial system. He had a tattoo on his forearm, which he said was from his time working as a sailor on a ship named Dixie. Given the time period, he most certainly did not work under the name Elizabeth Trondle, but whatever name he did use went unrecorded—as is often the case in historical records on people who crossed genders. But the papers did report that Trondle’s family had written him off as “incorrigible,”¹⁸ and that he had little contact with them.

At the time of his arrest, Trondle was wearing a “natty blue serge suit and trousers, with silk hose and tan oxfords.” A boy’s cap covered his closely shorn hair.¹⁹ Repeatedly offered other clothing by the police, he refused to change, asserting, “They can’t make me wear it if I don’t want to, and I won’t wear them, so there.”²⁰ He also refused to give his birth name and, when pressed, said that he would rather be sent to a reformatory than submit to the court’s wishes. “I’ve always been more boy than girl,” he told reporters on the steps of the courthouse.²¹

His plan, he informed Magistrate Voorhees during his arraignment, was to write to President Woodrow Wilson and request permission to wear men’s clothing. He was inspired by the case of Dr. Mary Walker, a physician, spy, and abolitionist who had received special dispensation to wear trousers after becoming the first female surgeon employed by the US Army (during the Civil War). To this day, Dr. Walker is the only woman ever to receive the Medal of Honor. Until her death in 1919, she traveled the country lecturing about dress reform, suffrage for women, and temperance. She was known to visit Brooklyn, and Trondle might have heard her speak or have at least read about her visits in the newspapers, which covered Dr. Walker’s comings and goings closely.

During his first night in the Raymond Street Jail, Trondle composed a short letter to President Wilson, which he shared with the court the next day:

Dear Mr. Wilson—I am a woman in trouble and I want my rights. It is no crime for a female to wear male attire, and yet I have been arrested here in Brooklyn for doing it. I want a permit from you or some one else to wear the costume I have adopted. I am tired of being kicked around and abused and poorly paid. If I can appear as a man and do man’s work, I shall be more respected, better paid and happier. Won’t you please see what can be done for me?²²

Newspapers around the country, from Texas to Kentucky to Rhode Island, printed the letter and some short details on Trondle’s case, taking Trondle from local news to nationwide infamy overnight.

Like Loop-the-Loop and Jennie June, Trondle was unapologetic about his desires and pushed back against the structures that attempted to control or thwart them. However, perhaps because Trondle was seen as a woman, neither the courts nor the police brought up inversion, homosexuality, or other terms relating to queerness. Unlike Loop or June, who used the word fairy to describe themselves, Trondle didn’t seem to have specific words for his identity (or at least not ones he said out loud). Information about “female” sexuality and gender transgression were not then widely available to the general public. This was just beginning to change—the same year that Trondle was arrested, an optometrist and typeface designer named Douglas McMurtrie began publishing a series of articles on sexual inversion in women, primarily based on the experiences of his friend Ruth Fuller Field and the queer actresses of her circle. Trondle certainly didn’t have access to those publications, but as his case wore on, others would soon bring sexology and queerness into the discussion—both to defend and condemn Trondle’s actions.

But first, what are we to make of Trondle’s various assertions to being a boy and being a woman, and why did I choose to use male pronouns for him? On its face, the economic explanation—that he was simply passing as a man to get gainful employment—seems a sufficient answer. However, Trondle’s family was well-off, and at seventeen, he probably wouldn’t have needed to work if he had been on good terms with them. Trondle reported at least one previous incident of running away and living as a boy (when he worked as a sailor and got a tattoo), suggesting that his gender identity was an ongoing issue. Trondle likely had no examples of transgender men to pattern his desires on, but he did know the story of Dr. Mary Walker, who claimed a female identity and said that she needed to wear pants because they made her job as a doctor easier. Asserting an economic rationale for his actions may have acted as a cover for Trondle’s transgender identity, while simultaneously providing the slim possibility that the president might grant him permission to live as he desired.

People arrested for cross-dressing often gave work-related explanations. When Christine Becrens, who worked as a maid, was arrested for dressing as a woman (as she had been doing for almost a decade), she told the Brooklyn court, “I cannot get work as a gentleman, so I dress as a lady.”²³ Similarly, when vaudeville performer Gus Seib was arrested for dressing as a man, Seib told the judge he “would be unable to obtain work as a woman.”²⁴ In both Seib’s and Becrens’s cases, it seems that while they cross-dressed to gain employment, they did so in part because their gender presentation was already so at odds with what was expected of them. This might also have been true for Trondle, as reporters were quick to note his deep voice and masculine mannerisms.

Although Magistrate Voorhees urged Trondle to wear women’s clothes if he expected any kind of “consideration” from the court (a suggestion Trondle pointedly ignored), Voorhees was also swayed by Trondle’s arguments.²⁵ Upon arraignment, Voorhees told the arresting officer, “It is no crime for a woman to dress in any attire she desires unless to commit a crime.”²⁶

This was a correct—although infrequently expressed—interpretation of New York state law, which made it a crime to wear a mask or costume only while attempting to commit another crime. The statute was based on an older law that was enacted in 1845 as a way to prosecute upstate New York farmers who rioted and fought off tax collectors while dressed in faux–Native American garments. However, in the late 1800s and early 1900s, the masquerade law was often used as an imprecise but effective method of prosecuting inverts. (Interestingly, the law would be revived again some one hundred years later to prosecute Occupy Wall Street protesters.)²⁷

This was yet another way in which the early 1900s were a transitional period for queer people in America: after the public had begun to recognize and name our existence, but before the legal system had had a chance to devise methods of enforcement and prosecution targeted at us. Instead, a patchwork of laws against vagrancy, disorderly conduct, solicitation, obscenity, prostitution, and being a public nuisance were pressed into service as necessary.

When the original charge failed to stick, Trondle’s probation officer returned with a new one: “associating with idle and vicious persons.”²⁸ More important, this new charge was overseen by a new magistrate who was much less sympathetic to Trondle’s case. The original judge, Voorhees, had a reputation for not being tough enough; in 1918, moral reformers in the Committee of Fourteen (an antiprostitution society that was just beginning to worry about queer people in New York City) wrote letters to the city government complaining about the lax sentences he doled out.²⁹ When the new magistrate sentenced Trondle to three years at the Bedford Hills Reformatory for Women in upstate New York, he made clear that the new charge was simply a useful pretense. “I sent her to the Bedford Reformatory,” he told papers, “because I believe she is a moral pervert. No girl would dress in men’s clothing unless she is twisted in her moral viewpoint.”³⁰ The word pervert did not have a specifically queer meaning at this time, but like sodomy, it was used to suggest a range of deviant sexual behaviors that included inversion. Although our legal system hadn’t yet been rewritten to prosecute queerness directly, the magistrate’s desire to do so is evident in this case. Even though Trondle’s style of dress was legal, it marked him as a degenerate person—a moral pervert—who needed to be put away.

Trondle’s case has a curious codicil. The day after his sentence was reported, a letter from Brooklyn resident Otto Spengler was published in multiple papers around New York City, arguing in support of Trondle’s right to wear men’s clothing. There “have been and no doubt always shall be persons of either sex whose inborn impulse will tend to dressing in the attire of the opposite sex,” Spengler wrote. These “naturally timid” individuals “dread anything like public exposure,” but “freedom in matters of dress means life and death to them.”³¹ To back up these assertions, Spengler cited the two most influential European sexologists, Magnus Hirschfeld and Richard von Krafft-Ebing, whose work inspired the entire American field of sexology.

Spengler knew all of this from firsthand experience. The same year that Trondle was arrested, a New York City gynecologist named Bernard Talmey presented a paper to the New York Society of Medical Jurisprudence on the cases of five “transvestites” that he had met through his practice; Spengler was one of them. A married German immigrant and parent of three, Spengler preferred the name Othilie, which is what she used when corresponding with a wide variety of other transgender individuals around the world. Some of these people would make up the source material for Talmey’s article “Transvestitism: A Contribution to the Study of the Psychology of Sex,” which he published in 1914 in the New York Medical Journal. In it, Talmey attempted to disentangle what we would call being transgender (which he, following in the footsteps of Magnus Hirschfeld, referred to as transvestitism) from being gay; he specifically mentions excluding someone who was “homosexually inclined” from the study.³²

Showing the growing influence of psychiatric theories of sexuality, Talmey wrote that transvestitism was “one of the newest discovered anomalies … where the sole psychosexual anomaly consisted in the desire for cross-dressing.” However, this didn’t stop Talmey from repeatedly suggesting that most of the people in the article might actually have been homosexual as well. Talmey wrote that Spengler “has no homosexual inclinations, but rather a profound repugnance to homosexual relationship … still he seems to want a man before whom he could expose the charms of his own person and who would kiss and caress him.”³³ That desire, however, is not expressed by Spengler herself anywhere in her direct quotes, which suggests that Talmey may have been putting his own interpretation on her impulses. Much like Dr. R. W. Shufeldt, Talmey found homosexuality disgusting; it was a “morbid sex state of gross somatic experiences … emanat[ing] from the crude powerful sensation of sex.” Transvestitism, on the other hand, he thought primarily an aesthetic desire for femininity, which explained why “the anomaly is found mostly in individuals possessing the so called artistic temperament.”

Spengler was not only out to other queer people and to Talmey; her entire family knew and accepted her identity. Her youngest daughter referred to her as “papa-lady,” and she shared lingerie with her wife.³⁴ She also corresponded with Dr. Mary Walker, whom Trondle had cited as his inspiration for the idea to write to President Wilson. Talmey’s article is perhaps most fascinating because it documents how connected queer people were becoming. Sexologists such as Talmey depended upon these preexisting networks to fuel their work, much as Ruth Fuller Field made Douglas McMurtrie’s writing on lesbianism possible, by introducing him to the wide world of women from whom he drew his observations (which included Field herself, as well as Johnstone Bennett, Vittoria Cremers, and Field’s girlfriend Emma Altman). Over the next two decades, Spengler would participate in sexological research studies of all kinds, and we will return to her experiences again in the 1930s, when she partook in one of the most groundbreaking studies of queer people ever attempted, undertaken by the Committee for the Study of Sex Variants. For now, though, her public defense of Trondle shows the extent to which queer people were beginning to actively find, recognize, and organize with one another.

The discussions around Trondle’s case make it clear the idea of queerness in women was becoming public knowledge that was both medicalized and stigmatized in ways that it simply wasn’t when Ella Wesner and Florence Hines were performing in theaters not far from the Adams Street Courthouse. This was part of a larger trend that was concerned with the rebellious sexuality of young women in general in the 1910s. The same Freudian theories of psychosexual development that began to shift discussions of queer sexuality from the body to the mind were also producing profound shifts in how teenage heterosexuality was viewed. Adolescence began to be seen as a time when teenagers needed to be assisted in order to reach proper emotional development. Those girls who failed to do so (prostitutes, lesbians, and others) were often labeled feebleminded, insane, or psychologically damaged. Increasingly, their minds, not just their bodies, were seen as broken—although that damage could still be divined from looking at their physical makeup. Adolescents like Trondle, who seemed inclined to go down a bad path, were increasingly brought under the thumb of the state—via the courts—who in turn handed them over to the emerging medicalized world of “mental hygiene” workers, such as the women who ran the Bedford Hills reformatory.

Medical and legal professionals made up two of the three pillars upon which the emerging regulation of queer sexualities was being built. The third? Civilian morality organizations. Trondle’s case shows the difficulties of attempting to prosecute queer people through the courts in the early 1900s. However, there was an active world of extrajudicial antivice organizations in New York City which dated all the way back to the Society for the Reformation of Juvenile Delinquents (the organization funded by the Concert Saloon Law). These groups were happy to step in and take up the slack. One of the most powerful was the Committee of Fourteen (so-called for its fourteen founding members), which formed in 1905 to shut down what were known as “Raines Law hotels.”

Raines Law was an 1896 state statute that banned the sale of alcohol on Sundays. As Sunday was the day most working-class men had off, this was an early form of pro-temperance social control, aimed at reforming the drinking habits of the poor. Tellingly, hotels with more than ten rooms were exempted from the law, meaning that traveling gentlemen could still partake as they saw fit. Saloon owners soon began to take advantage of this loophole by carving up their second floors or public halls into small rentable rooms. By 1900, Brooklyn had some 1,664 official hotels.³⁵ Sex work, which had been driven out of the theaters by earlier waves of reformers, relocated to these Raines Law hotels. These spaces also facilitated sex between unmarried heterosexual couples by providing cheap, easily accessible semiprivate space, which was rare in this time of crowded tenement living. Here again, the lines between sex work, casual sex, and dating blurred easily. Women who had premarital sex for pleasure at Raines Law hotels were just as likely to be arrested for prostitution as were women who actually exchanged sex for money.

To combat this new scourge, leading businessmen, clergy, socialites, doctors, judges, and politicians formed the Committee of Fourteen in 1905. By 1911, Brooklyn had such an active nightlife scene that it became the only borough with its own specific auxiliary branch of the committee. This branch worked primarily in two neighborhoods. The first was the waterfront district closest to Manhattan, from the Brooklyn Navy Yard in the east, down along Sands Street to the City Hall area (where the New Park Theatre stood) and over to Columbia Heights, the street that bordered the water on the western edge of Brooklyn Heights. The committee often referred to this area as “the Adams Street tenderloin district,” and it encompassed parts or all of the neighborhoods we now know as Dumbo, Vinegar Hill, downtown Brooklyn, and Brooklyn Heights.³⁶ The other area that had a particularly active underworld sex trade? Coney Island, whose reputation as a hedonistic playground had only grown since the days of Florence Hines. According to Timothy Gilfoyle, the historian of prostitution, in the early 1900s these two neighborhoods were “synonymous with commercial sex.”³⁷

Two important inaugural figures in the Committee of Fourteen’s Brooklyn auxiliary were the husband-and-wife pair Sarah Truslow and Robert Latou Dickinson. Truslow was a steely-eyed social reformer who also founded the first YWCA in Brooklyn; Dickinson was a doctor specializing in gynecology and maternal health. Both were born and bred Brooklynites who grew up in the downtown waterfront area. Truslow remained active with the Committee of Fourteen for over twenty years, until it shut down in 1932. Dickinson’s involvement was briefer, but his experiences with the committee would spark an interest in queer and deviant sexualities, which would eventually lead him to help organize the Committee for the Study of Sex Variants (who would in turn examine Othilie Spengler in the 1930s).

These reform-minded upper-class men and women sought to bring their social power to bear against immoral activities in a variety of ways. Most directly, they employed informants who visited saloons throughout the five boroughs looking for unescorted women, prostitutes, pimps, degenerates, fairies, mixed-race socializing; hotels that rented rooms to unmarried couples; and saloons that served alcohol on Sundays, to men in uniform or without licenses. When they found these violations, they contacted the brewers connected to the saloons. Most saloons were “tied shops,” which meant they worked with a single alcohol supplier.³⁸ These breweries usually owned the bars that sold their products or had a controlling interest in them, but the bars were run by local managers, who applied for a state liquor license to do so. By shaming them or threatening legal action, the Committee of Fourteen forced breweries to withdraw their imprimatur from saloons the committee considered to be operating immorally. If the committee felt it had enough evidence to charge a saloon operator with actual criminal activity, it worked directly with the police (though those collaborations were often fraught, with the police viewing the committee members somewhere between helpful informants and moralizing zealots). Finally, the committee also heavily lobbied for laws that made it easier to arrest people for vagrancy, prostitution, solicitation, disorderly conduct, and the keeping of a disorderly house. (This phrase referred to any dwelling that was considered a public nuisance, be it brothel, private club, or simply a raucous home.) The law, they realized, was slow to change, but they could be nimble, following vice however it tried to escape the widening net of police repression.

In this, they were startlingly effective. By 1912, they had reduced the number of Raines Law hotels in Brooklyn to just three hundred, shuttering or driving underground more than thirteen hundred establishments in just seven years. In their success, the committee saw the opportunity to expand further. In an annual report issued in January 1912, Chairman Frederick Whitin wrote that the committee had “become conscious of the need of a much larger work which must be done.”³⁹ From this point on, the committee would combat any sexual vice in any commercial venue. This broader purview set them on a direct collision course with some of the earliest queer public institutions in Brooklyn: bars that served queer men around World War I.

In July 1914, just a year after Elizabeth Trondle was arrested, the “Great War” began with the assassination of Archduke Ferdinand of Austria. World War II is often cited as the moment when many men and women, uprooted from their homes and thrown together in single-sex barracks and factories, became cognizant of queerness (their own and others). But World War I had just as profound an effect on the lives of many gay men and lesbians, if on a smaller scale. Margot Canaday, in her book, The Straight State, argues that World War II was when “military officials developed and implemented a policy solution to deal with what they learned about perversion during World War I.”⁴⁰ Many people, not just in the army, were learning about homosexuality around this time. In the lead-up to World War I, The New York Times printed the word homosexual for the first time, in an article by playwright George Bernard Shaw. Shaw was a pacifist (and at times a vocal proponent of sexual rights), but in the final paragraphs of his article, he made it clear that didn’t mean he approved of decadent German society. Instead of war, he wrote, we needed “to trust to the march of Democracy” to condemn such institutions as “the forty tolerated homosexual brothels of Berlin … [to] the dustbin.”⁴¹ The war did little to Berlin’s queer subculture, which would flourish during the Weimar Republic of the 1920s. But it would prompt extensive collaboration among the Committee of Fourteen, the police, and the military, which led to the first recorded legal action against a gay bar in Brooklyn.

Through a deal proffered by Chairman Whitin, the committee functioned as the “eyes and ears” of the military police at training camps throughout the Northeast, from Atlantic City, to Philadelphia, to Brooklyn.⁴² The committee was well aware that the war was causing an uptick in homosexual activity, which they blamed on “the great influx of sailors.”⁴³ Chairman Whitin was blunt in his belief that homosexuality “has been an evil among sea-faring men from time immemorial.”⁴⁴ Thanks to the Navy Yard, Brooklyn was flooded with sailors throughout World War I. At the start of the war, the yard was already the largest in the country, employing some five thousand men on its massive, hundred-plus-acre campus. By the time the war ended in 1918, its rolls would swell to some twenty thousand, according to labor historian John Strobo. As a result, the Navy Yard area would be “flooded with young men, far from home and lonely.”⁴⁵ One Committee of Fourteen investigator described the area as being overrun with rowdy sailors and loose women. In a report about street conditions on a random Wednesday evening, he wrote:

It seems to me that the sailors were sex mad. A number of the sailors were with other men walking arm in arm, and on one dark street I saw a sailor and a man kissing each other. I saw a few sailors enter one of the hotels with these men, who I judged to be perverts, and register for rooms. It looked like an exhibition of mail [sic] perversion showing itself in the absence of girls or the difficulty of finding them. Some of the sailors told me that they might be able to get a girl if they went “up-town” but it was too far up and they were too drunk to go way up there.⁴⁶

Instead, many of these men found comfort with one another in the saloons, hotels, and alleys of Brooklyn’s waterfront. In turn, the Committee of Fourteen found them.

On the evening of January 14, 1916, Antonio Bellavicini went to work at a nameless saloon at 32 Sands Street, about halfway between the Brooklyn Bridge and the Navy Yard. Located on the corner of Adams Street, two steps down from the sidewalk, this saloon was in the shadow of one of the elevated trains that prefigured the subway. Sands Street had a reputation as one of the worst streets in Brooklyn, where tattoo parlors and cheap chop-suey joints catered to sailors and sex workers all night long. Despite being a bitterly cold January night, with temperatures expected to dip into the teens,⁴⁷ the saloon was busy with sailors and civilians out for fun on a Friday. Unbeknownst to its patrons, the bar had been under the watchful eye of the Committee of Fourteen for “three or four weeks” because it was “frequented by degenerates.”⁴⁸ According to the committee’s records, it was a “resort of male perverts, catering to sailors,” one of the first they had come across in Brooklyn.⁴⁹ Under intense pressure to preserve the moral standing of the military during wartime, the committee was eager to shut the saloon down.

Photograph of 32 Sands Street in the year 1913, three years before it was raided by the police and the Committee of Fourteen for serving homosexuals. (Photo courtesy of the Brooklyn Historical Society. W.J. Mullen, [32 Sands St], 1911, photographic print, v1973.2.34; Brooklyn Historical Society.)

However, there was a problem: it was not illegal for homosexuals to gather in public, nor for bars to serve them. The year before, the committee had successfully worked with a Brooklyn assemblyman to amend the vagrancy law so that police no longer needed to prove that a woman exchanged sex for money, just that she was loitering with the intent of encouraging lewdness. This much lower standard of evidence allowed the police to arrest virtually any woman they deemed immoral. A “prostitute,” in their eyes, was no longer a woman who accepted money for sex, she was a degraded person who could be jailed for who she was, not for what she had done. But when it came to homosexuals, the law still revolved around sodomy, disorderly conduct, creating a public nuisance, and masquerading in clothing of the opposite sex—all specific, actionable activities that the police could be called upon to prove in court. If they were going to raid a bar such as 32 Sands Street, they needed to catch its patrons committing one of those offenses.

On that cold January night, they used a novel strategy to do so: the police disguised Officer Harry Saunders in a US Navy sailor uniform and sent him into the bar on an entrapment exercise. If any of the patrons hit on him, they could be arrested for disorderly conduct.

Around 10:00 p.m., Officer Saunders entered the bar and ordered a beer. Almost immediately, three men at a nearby table called out to him, saying, “Sailor, dear, come over and drink with us.” After a second round of beers, Officer Saunders asked why the men had called him over. A man named John Meehan responded by inviting Saunders to 170 Schermerhorn Street. “If you will come down there,” he offered, “we will suck your cock.” Meehan assured Saunders that everyone in the bar—some ten or twelve individuals, plus Bellavicini, the bartender—were “all the same.” After three men at another table also hit on Saunders, he dropped a quarter on the bar for his drinks, then promptly arrested all six men who had spoken to him (and Bellavicini). The entire raid took about fifteen minutes.

All six patrons were convicted of disorderly conduct, a misdemeanor, and sentenced to six months in the workhouse. Had the police contented themselves with this, the case of 32 Sands Street would have been lost to the view of historians, since these arrests generated no publicity and no trials, and the charge was no different from what other men might have gotten for public intoxication. But in this case, the police, most likely at the urging of the Committee of Fourteen, overstepped their bounds and arrested Antonio Bellavicini for keeping a disorderly house. On February 1, Bellavicini was tried, convicted, and sentenced to three months in the workhouse. Unlike the other men, Bellavicini—a married, thirty-four-year-old, Italian-immigrant father of five—fought back. He hired a lawyer named John J. McGinniss and appealed his case. The resulting trial transcripts were preserved by the New York State Court of Special Sessions, and they are a gold mine of information for the historian attempting to reconstruct New York City’s early, incoherent attempts to police homosexuality.

Bellavicini’s appeal rested on three points. One, that he hadn’t heard the men talking with Officer Saunders and therefore could not be expected to have known they were committing an offense. Two, that even if those men had said what Saunders accused them of, that was an isolated incident and the law around keeping a disorderly house required repeated, flagrant disorderly conduct. Three, that it was impossible for any judge to issue a fair ruling in a case related to homosexuality because “the character of the charge awakened their innate hostility to such vice as was alleged, created an irremovable bias in their minds and suppressed their judicial temperament.”⁵⁰ The court, unsurprisingly, was not sympathetic to this last line of defense, but it at least considered the other two.

During Bellavicini’s appeal, the three police officers involved in the raid suddenly shifted their stories in an attempt to undermine his defense. Now, they said, the men in the saloon had all been wearing makeup and carrying powder puffs. Moreover, two sailors were sitting on the laps of other men in the back room of the saloon. These details had never been mentioned earlier. Even if Bellavicini hadn’t heard the solicitation, the district attorney argued, he should have been able to tell that these men were degenerates by the way they dressed and acted. These behaviors inherently created a public nuisance, which meant Bellavicini was guilty of keeping a disorderly house. Multiple other men, including a sailor stationed at the Navy Yard, testified that no one wore makeup, and that only one person—other than Saunders—was in a sailor’s uniform in the saloon that night. The district attorney attacked their credibility in his cross-examination. In particular, he went after the sailor who testified that no other sailors were in the bar, and no men with “blackened eyebrows” or “rouged cheeks” either. The DA attempted to destroy the sailor’s trustworthiness as a witness by tricking him into admitting that he could not name the master of arms on his ship, then telling the judges that the position of master of arms had been abolished by the navy. When Saunders’s attorney objected and requested an adjournment for time to show that ships still employed masters of arms, the judges brushed him off.

Bellavicini lost his appeal, though two of the judges were persuaded by his arguments. Judge Stapleton, in writing the court’s dissent, said, “Although there is competent evidence of an isolated, indecent or obscene act … there is no evidence that painted men with effeminate voices resorted there with the knowledge of defendant.” The lead three judges, however, ignored this issue entirely, basing their verdict on police testimony that they had had the place under observation for weeks. What happened that night, the judges reasoned, was less important than the ongoing events that had attracted police interest to the saloon in the first place—even though no testimony or evidence from the trial related to those weeks of observation. Bellavicini was sentenced to three months in the workhouse for keeping a “place of public resort at which the decency, peace, and comfort of the neighborhood were disturbed.”⁵¹ After that, Bellavicini disappeared from public records entirely.

Slowly, the state was inching toward an understanding that homosexuality was an identity, not a set of actions, and that the mere existence of queer people in public was dangerous to the community—much like the existence of immoral women. In the cases of Elizabeth Trondle and 32 Sands Street, we can see the police bumping up against the limitations of the law, which had been written to deal with criminal behaviors, not criminal classes of people. Reform organizations such as the Committee of Fourteen would be essential in getting legislators to amend the necessary laws to account for this emerging new understanding of sexuality. It had taken the reformers nearly a decade to change the laws defining prostitution; it would take a little longer to change the laws regarding homosexuality. But they would ultimately succeed in the 1920s, as the Committee of Fourteen was nothing if not diligent. However, Bellavicini’s case also shows the extent to which the police were able to bend existing laws into service when it came to criminalizing queer people. More pointed legislation would make this job easier, but it wasn’t strictly necessary, as Bellavicini unfortunately discovered. Ultimately, what mattered was not whether he had broken the law (as the police were fully capable of manufacturing whatever evidence was necessary), but whether he was considered a priori guilty because of who (or what) he was. In other words, the law lagged behind social understandings of right and wrong.

For their part, the committee was overjoyed that they were able to help “get the perverts” at 32 Sands Street, and Chairman Whitin personally sent a note to the acting police commissioner congratulating Officer Saunders on his undercover work.⁵² Whitin also wrote to the head of the State Excise Department in Albany, which oversaw liquor licenses, to ensure that 32 Sands Street was shut down for good.

Throughout the 1910s, similar raids appear to have been conducted by the police and the Committee of Fourteen, but because they generated no trials, there is almost no information about them. For instance, a small note in the committee’s files relates to a similar case in 1913, where the police, in cooperation with the military, also used an officer dressed as a sailor to entrap men drinking at 36 Myrtle Avenue, a saloon-hotel “used by male perverts.”⁵³ Since no one challenged these arrests, they generated no other paper trail—although someone in the committee did scratch an angry message in pencil at the bottom of the page to note that using a sailor uniform in this way was in “flat disregard” of federal law and should be discontinued. A few years later, in a list the police shared with the committee on August 23, 1915, it’s noted that the Commercial Hotel, located in downtown Brooklyn at 254 Fulton Street, was a “meeting place for degenerates.” The undated notes of one of the committee’s paid informants briefly mentions a saloon at 1120 Myrtle Avenue in Brooklyn, where a man named Harry, “said to be a fairy,” performed women’s songs in an effeminate voice and manner.⁵⁴ But there’s little other information about any of these places.

Of slightly more interest is the case of Bonner’s Saloon, located not far from 32 Sands Street and the Navy Yard. In 1910, Bonner was listed in the US census as being a single, twenty-five-year-old black man from North Carolina who was living across the street from his saloon, which was on the second floor of a nondescript building on Myrtle Avenue. Bonner was the rare black bar operator who came to the committee’s attention. In their reports, the committee noted that it was hard for them to gain access to establishments for people of color, since almost all of their investigators were white, and they devoted little resources toward policing the bars and neighborhoods where people of color congregated (another reason why the queer history of people of color in Brooklyn lacks records).

The earliest public mention of Bonner’s Saloon is a newspaper report from 1910, when a card game gone wrong led to a shoot-out; Bonner killed the gunman and was acquitted for self-defense.⁵⁵ Two years later, the police attempted to frame the saloon for illegally serving alcohol on Sunday, but the case was dismissed for lack of evidence, with The Brooklyn Daily Eagle going so far as to call the police a “strong arm squad.”⁵⁶ However, by 1913, the Committee of Fourteen crowed in their bulletin that they had succeeded in having the place shut down and reopened under new ownership, though just how they did so is a mystery.⁵⁷

Clearly, Bonner’s was a thorn in their side. But why exactly? Two reports from committee investigators suggest some answers. In a visit in 1912, the investigator noted that the “tone” of the saloon was actually “above the other places observed.” Although the bar was playing ragtime—a distinctly black style of music that was considered racy and sexual—it was not “out of the ordinary or vulgar.” This was in sharp contrast to the supposed immorality the investigator observed. He seemed particularly upset by the bar’s distinctly interracial clientele. He saw black men drinking with white women (three of who, he noted, seemed to be there expressly to “solicit colored fellows”), and white men hanging out with black women (who were having a “very big and loud time”). Later, when two black women came to sit with him, he inferred that they were prostitutes because they invited him home with them after he purchased a round of drinks. All unescorted women in bars were generally assumed by the committee to be prostitutes, or at least prostitute-adjacent, but black women came in for particularly harsh scrutiny.

In a separate, undated report, a different investigator commented with horror that blacks and whites at Bonner’s were “mixed in with each other like hash.” This investigator also noticed another kind of immorality: “the presence of fairies.” Fairies, he explained, were “a very effeminate type of man.” As in the case of 32 Sands Street, the mere existence of gay men in public was seen as an indicator of criminality. “Whether or not they were soliciting trade I cannot say positively,” the investigator wrote, “but I am not willing to give them the benefit of the doubt.”⁵⁸

(The term trade, as used here, was a common way of referring to the customers of sex workers, which would later be extended to refer to any masculine and/or straight-identified men who had sex with men. Just as fairies were seen as equivalent to prostitutes, the men who slept with them were considered the same as johns.)

Although they may seem only slightly related, fears about “race mixing” and queer people were intimately connected, flip sides of the same eugenic coin. Both fears, ultimately, were about preserving the “white race.” Black people represented an external threat to whiteness; queer people represented an internal one. After emancipation, white scientists, lawmakers, and doctors saw a looming threat of extinction, through the degeneration of white bloodlines via interracial relationships on the one hand, and through sterility and enervation via homosexuality on the other. Because these were ultimately sexual issues, it’s no wonder that American sexology, even more so than its European counterpart, was deeply racist. Some of the same eugenic scientists who were defining “homosexuality” in this era were also (re)defining whiteness, primarily by promoting the idea that black people were both a physical and existential threat to the so-called white race. They argued that ethnic differences among Europeans were nothing when compared to the differences between whites and blacks. Whiteness at this time was a less unified identity, with much being made over intra-European ethnic divisions. Irish people, southern Italians, and Jews of European descent were only tentatively considered white by most New Yorkers. Only once larger numbers of black Americans moved to the city during the 1920s did whiteness come to be understood as the pan-European identity it is today (and still today, European-descended Jews are often viewed as racially other). Sexologists would be integral to this unification of the “white race.”

The 1910s were still a very white time in Brooklyn’s history; marginal gains had been made in the population of people of color around 1900, but by 1910, Brooklyn was once again 98.54 percent people of European descent, according to the US census—about the same percentage as Staten Island, slightly whiter than Manhattan, and a little less white than the Bronx or Queens. In real numbers, this meant some 22,000 black people in Brooklyn; 1,000 people of Asian descent; 146 people listed as “other”; an uncounted number of Latinx people; and 1.6 million whites.⁵⁹

R. W. Shufeldt, the doctor who photographed Jennie June and Loop-the-Loop, was prototypical of the doctors involved in racist American sexology. In his 1915 book, America’s Greatest Problem: The Negro, he argued at length that “the black races of mankind came nearer the anthropoid apes than any of the white races did.”⁶⁰ In Shufeldt’s view, black men were violent rapists, and black women were licentious, promiscuous, and purposefully trying to seduce white men. Or as he put it:

It is the aim and highest ambition of the negresses to have children by white men, for the reason that such children, by the superior intelligence coming from their white fathers, will command better positions when they grow up than the pure blacks, and in so doing will powerfully further the interests, political and otherwise, of the African population in this country.⁶¹

Shufeldt believed that white perverts were helpless before their “sexual disability.” He argued therefore that homosexuality, pederasty, sodomy, and transvestitism (among other “disorders”) should not be criminalized. Instead, he believed in a dystopian future like that which Aldous Huxley would soon describe in Brave New World. Only science, Shufeldt thought, could save white people from queers:

We will continue to breed millions of sexual perverts and inverts—psychopathic types—just so long as any ignorant priest, justice of the peace or other party, is permitted to give people permission to breed them, that is, without the would-be parents having first been examined by a competent medical expert.⁶²

In other words, to prevent homosexuality, it was necessary to more closely police heterosexuality, which was work that doctors such as Shufeldt and reformers such as the Committee of Fourteen were more than happy to take on. Throughout the 1910s, a series of state laws were introduced with the aim of controlling reproduction—and thereby saving the white race. In both 1910 and 1913, New York State tried to pass a law requiring that couples obtain a physician’s certificate before getting married, as Shufeldt wanted, although it failed both times. In 1912, the Committee of Fourteen worked with doctors to pass the McClellan-Brush Bill, which empowered a three-person board of medical experts to examine and sterilize “the feebleminded, idiotic, epileptic, and a certain class of criminals confined to state institutions.” In their bulletin, the committee noted that similar legislation had already been passed in Indiana, Connecticut, New Jersey, California, and Michigan.⁶³ Throughout the decade, as previously discussed, the committee also pushed for stricter laws regarding heterosexual prostitution. None of these laws directly addressed queer people or desires, but preventing the birth of “sexual perverts and inverts” was an explicit goal of the men and women who created these laws. Just as queer people were becoming more connected, a parallel and increasingly tight web of sexual control was being woven among doctors, the police, and upper-class moral reformers.

During this period, psychological and medical experts became intimately involved in the criminal justice system at every level, from running reform institutions such as Bedford Hills, to testifying as expert witnesses in cases such as the murder of James Vickers, to sitting on parole boards, to performing studies on incarcerated people. From these newfound positions of power, they attempted to enact their eugenic ideas about sexuality and race. Elizabeth Trondle and Antonio Bellavicini had been prosecuted using inexact laws that were not created to police sexuality; over the next two decades, the triumvirate of police, doctors, and moral reformers would create laws and policies that explicitly targeted queer people.

By July 1919, the Committee of Fourteen was well aware of the growing queer community and the limits of the law. In one of their regular internal bulletins, they wrote that “the number of convictions for degeneracy was very much larger than here reported,” but that without better legal tracking, it was “impossible to learn the number of such cases.”⁶⁴

At the same time, however, it was becoming increasingly possible to live a queer life in America, in New York City, and in Brooklyn. Attempts to repress sexuality were becoming more complicated and powerful precisely because queerness was becoming more common and well known. The scattered moments of queer sexuality that had existed in earlier decades had begun to coalesce into a critical mass. The idea of a “gay man” or a “lesbian woman” had become thinkable in America in a way that it simply wasn’t before this time. Brooklyn’s next crop of queers would in many ways share our current understanding of sexuality as a fixed part of one’s psychological makeup, which was distinct from, but related to, gender. Perhaps the critical difference between this new generation of queer people and those who came before them, however, is that queer people post-1920 found one another in dense enough numbers that their stories have been preserved not just by doctors or court transcripts, but by their own words as shared with other queer people. The private lesbian theater circles of Ada Dwyer and Johnstone Bennett, the transgender networks of Othilie Spengler and Loop-the-Loop, and the small-time saloons run by Antonio Bellavicini and Robert Bonner were the precursors to a more robust and self-organized queer world that would grow in the 1920s and 1930s.

Brooklyn was also changing. From 1900 to 1920, the borough nearly doubled in size, until it was home to more than two million people. Although the original waterfront—the downtown area nearest Manhattan—would remain important, the booming population meant that other areas of Brooklyn were developing the kind of urban density that allowed queer life to flourish. Moreover, during the 1910s, the New York City subway finally penetrated Brooklyn in a meaningful way. Previously, the borough’s mass transit had been a patchwork of trolley cars, elevated trains, horse-drawn omnibuses, ferries, and sloops. Starting with the Brooklyn Loop Lines (which opened in 1913), subway cars were sent over the bridges and into downtown Brooklyn for the first time.

These initial lines made the Brooklyn waterfront more attractive to potential residents and businesses, by making them less remote. A number of artists would leave Greenwich Village for Brooklyn Heights in the 1920s, cementing its reputation as Brooklyn’s bohemian enclave. However, the subway also contained within it the seeds of the waterfront’s downturn. In the latter half of the 1910s, new subways would be built to connect these first Loop Lines to other areas of Brooklyn, as well as to Queens and Manhattan. This was a conscious attempt to reorganize the city’s population and reduce the density of areas such as lower Manhattan and downtown Brooklyn. Within a decade of the first subway’s coming to Brooklyn, seven more lines crossing the East River would begin operation. Laborers who once needed to live near the water to be near work could now easily move into farther-flung parts of the city.

All of New York was suddenly vastly more connected than it had ever been. Thanks to the subway, in the coming decades, a queer Brooklynite would be able to loaf about at a bathhouse on Coney Island, get a drink at a saloon in Greenwich Village, stop by a rent party in Harlem, and then cruise for sailors at the Brooklyn Navy Yard, before easily returning to his apartment in Brooklyn Heights. Prior to this, all commuters had to stop at the edge of the East River and switch from one mode of conveyance to another, but the subway allowed for one continuous ride. Soon, people would not only not need to live near the waterfront, they would no longer have to stop there at all.

However, the subway didn’t just connect preexisting queer spaces; it also created them. The subways accidentally provided a vast network of sexual hot spots for queer men, in their public bathrooms. If subway cars were like packed clubs, tossing New Yorkers against one another millions of times a day, then the men’s room was decidedly the after party. The subways are a perfect metaphor for queer life in the Roaring Twenties: new, exciting, fast, vast, and growing.