In the mid-1870s the police regularly arrested a person called Jeanne Bonnet who always wore “male attire.” In contrast with DeWolf’s dress reform clothing, Bonnet preferred the stylish “hoodlum” suits worn by the city’s young and rowdy working-class men; with her short hair, narrow build, and a penchant for hard liquor, she regularly moved through city space as a man. Bonnet hung out in the bars and brothels along Dupont Street, befriending Barbary Coast women and persuading at least one local sex worker, Blanche Buneau, to leave prostitution and her exploitative lover. The police arrested Bonnet more than twenty times for cross-dressing and occasionally brought additional charges. For example, when the police realized that the masculine figure drinking at the bar was a woman in men’s clothing, they arrested Bonnet for violating not only cross-dressing law but also the local dive laws that banned women from entering bars. This harassment ended only in 1876, when an unidentified gunman shot and killed Bonnet in Blanche Buneau’s bed. The murder was never solved, and Buneau disappeared from the historical record. [...]

In October 1890 a judge sent Dick/Mamie Ruble to the state insane asylum because of “a hallucination that she should wear men’s clothing and wants legal authority for doing so.” Ruble was arrested for violating cross- dressing law, but the case took a dramatic twist in court, when Ruble refused to identify with available gender categories and explained to the judge, “I’m neither a man nor a woman and I’ve got no sex at all.” While many cross- dressing offenders pled for mercy and claimed their crimes were innocent “pranks,” Ruble challenged the judge to locate femininity on his/her muscular body: “Did you ever see a woman with a hand like that Judge . . . ? Look at that muscle. Oh I tell you I couldn’t pass for a woman anywhere, even if I tried.” Unimpressed by Ruble’s declarations, the judge called in the police surgeon, who referred the case to the Insanity Commission, located in a small basement room in city hall. The two-member commission reviewed the case, declared Ruble insane, and ordered his/her indefinite commitment to the Stockton Asylum, where the admitting doctor noted that Ruble “imagines she is a hermaphrodite. Wears male clothing. Wishes to have legal authority to wear men’s clothing.” Such “evidence of insanity” doomed Ruble to life in the asylum; s/he remained there for eighteen years, until dying from tuberculosis in 1908. [...]

Similarly in 1899 the commission found Sophie Lederer to be insane, noting that the twenty-three-year-old domestic worker “talks irrationally— acts silly and claims to be a boy.” Pohlmann spent two months in the Stockton Asylum before being deported to Germany, while Lederer effectively received a life sentence, dying in the asylum of heart disease in 1908.

Although Murray always denied being a lesbian, she occasionally admitted to “homosexual tendencies” as the only available descriptor that people would accept. As for the report that she was taking hormones, nothing in her correspondence with doctors supports that claim. She wanted testosterone badly enough, however, that she may well have told the corrections officer that doctors had agreed to give it to her. Barry did not arrest Murray for hitchhiking but rather escorted her to the New York City Police Department, where officers decided to take her to Bellevue Hospital. There, Murray poured out her story to a psychiatrist, who gave her a diagnosis of “schizophrenia.” In the doctor’s view, she suffered from a delusion: she believed that she was a man. Permitted to call a family member, Murray contacted her “cousin” Mac. The next day, Mac checked her out of Bellevue and, probably on the recommendation of Dr. Chinn, took her to a private psychiatric facility, Dr. Rogers’s Hospital, at 345 Edgecombe Avenue, on the corner of 150th Street. Murray was lucky. If Mac had not come to her rescue, Bellevue psychiatrists were prepared to seek her commitment to one of the vast, overcrowded state hospitals for the mentally ill. On the typewriter Mac brought to her, Murray itemized the causes of her “nervous collapse”: overwork; lack of desire to either eat or sleep; anxiety over parental responsibilities; and the “temporary disappearance of a friend.” All of these factors played a part; however, Murray believed that the principal source of her emotional crisis was the same problem with which she had wrestled for a decade: the fact that she repeatedly fell in love with women without having any “opportunity to express such an attraction in normal ways,” that is, as a heterosexual male in love with a heterosexual female. The only people who seemed to accept her for who she was were “the unsophisticated people in the environment” [people like her aunts and the ever-loyal Mac] who “accept me pretty much as one of nature’s experiments; a girl who should have been a boy, and react to me as if I were a boy.” Doctors at the Rogers hospital proved no more willing to cooperate in Murray’s efforts to become the man she knew herself to be than those elsewhere. When they released her in mid-March, she had nothing to show for her stay beyond a medical bill for $80, which she could not pay.

Alison Stewart: You were able to access your medical records and you put them actually in the memoir. Dylan Scholinski: Right. Alison Stewart: What did the medical records reveal to you about how the medical establishment was thinking about you and then they were thinking about your treatment? Dylan Scholinski: Well, some of it was very diagnose-based. Like I said, I think they saw the cure for my depression if I would just learn how to be more feminine. That was the treatment that I was supposed to learn about what boys like. They actually put me in some really unsafe situations, hoping to inspire sexual behavior in order for me to be more feminine. They were putting me in situations that seem really unreasonable and unsafe. Alison Stewart: Could you share a few? Dylan Scholinski: When I was put into my third hospital, they put me on an all-male unit. I was the only girl on an all-male unit. I was the first girl to be. That's when it switched to not being an all-male unit. That in and of itself, you're like a little piece of meat there in the middle of 20 young men. That would be an example, or having me in four-point restraints and having male patients sneak into my room while I had no way of defending myself. Alison Stewart: At one point, you had to start wearing makeup in order to gain good points for good behavior. Dylan Scholinski: Right. Alison Stewart: What did it feel like when you wore makeup? Dylan Scholinski: Oh, my God, you feel dead. It causes a separation from your body. That is kind of hard to explain. I was on a point system. I would receive points for good behavior and lose points for bad behavior. My treatment was I was supposed to learn how to apply makeup and then say something nice about myself. Nice not being like I'm really good at baseball or I can really hit the ball or I can run really fast or any of these other things, or I can draw things that I was really proud of. Instead, I had to say things like, "I love looking pretty." I would feel like such a liar that I was performing and deceiving. I think they were hoping if I repeated it enough that it would change who I was going to become.