Prisoners, Doctors, and the Battle Over Trans Medical Care

Reiyn Keohane’s handwriting is tidy, with small, looping letters, lots of exclamation points, and the occasional smiley face. Months after I received my first letter from her, Keohane, who is 27, called me. At the time, she had been in the Wakulla Correctional Institution, just south of Tallahassee, Florida, for five months. In a lilting voice and a faint drawl she talked about growing up in Fort Myers. She told me how, as a kid who’d been assigned male at birth, she watched Ellen DeGeneres with her mom and thought, “I want to be like that when I grow up.” At 14 she came out as transgender. Her mom took her shopping in the women’s department at Macy’s. She grew her curly, walnut-colored hair out to her shoulders.

From that day forward, Keohane identified as a woman. In the coming years, she sought treatment for intense feelings of dysphoria, obtained a gender dysphoria diagnosis, and changed her legal name. Then, in 2013, she was arrested for stabbing a roommate. The evidence presented in the available court documents suggests that Keohane attacked the other woman, then fled the scene, and she pleaded guilty. (Since at least 2017, however, Keohane has insisted she was acting in self-defense, and she recently hired an appellate attorney in an attempt to overturn her plea.) After receiving a sentence of 15 years, Keohane arrived at the South Florida Reception Center in leg irons. She handed over everything she’d brought with her—legal papers, stamps and envelopes, bras, and underwear—to a prison employee and was handed a set of boxer shorts, a T-shirt, and a blue shirt and pants. Then she sat in a tattered chair and, as a line of men waited their turn and watched, a barber sheared off her hair.

More than 20 percent of trans women (and nearly 50 percent of Black trans people) have been incarcerated at some point in their lives, driven into the criminal justice system by over-policing and poverty as well as structural and individual discrimination. Once they end up behind bars, almost all are incarcerated according to the sex they were assigned at birth. That means being locked up in men’s facilities, where many experience long stints in solitary confinement and near-routine physical and sexual violence at the hands of both prisoners and guards.

Though she’d lived as a woman in the years preceding her arrest, Keohane had been placed in a men’s prison, where she wasn’t allowed to grow out her hair or get the clothing, body wash, or deodorant available at the women’s prison. These could be seen as inconsequential things, but to Keohane they were essential. As a kid, she says, her parents had refused to let her take hormones, but at least she’d had control over how she dressed and wore her hair. When she was 19, she started hormone therapy, but now the Department of Corrections, in apparent violation of its own policy, was denying her that treatment too. In a men’s prison, wearing men’s clothes, she felt severed from the lifelines that had sustained her.

In October, three months after she arrived, she ripped a shirt into strips to make a rope. She then tied the noose around a shower bar. Prisoners on the cell block could see what was happening, so they started yelling and pounding on their doors. A guard rushed in and cut her down. In the subsequent weeks, Keohane implored prison officials to let her dress as a woman. “I have lived my entire life past the age of 13 as female, and it is extremely detrimental to my mental health to forbid this practice; it is also well documented as a legitimate and proper treatment for a person who is transgender,” she wrote to prison administrators in December 2014. They denied her requests. A month later, she cut her scrotum with a razor in an attempt to remove it.

After recovering, she began to carry out a secret rebellion. She cut up the standard-issue clothing and sewed makeshift panties and bras, knowing she could get in trouble if she were caught wearing them. She lived in a constant state of vigilance, but following the rules was out of the question. In the fall of 2015, after failing to get prison officials to provide her hormones and let her present as a woman, she wrote to the American Civil Liberties Union of Florida asking for help. Daniel Tilley, now the organization’s legal director, agreed to take on her case.

An oddity of medical care in the US is that access to it is a constitutional right—at least on paper—for a single category of Americans: the incarcerated. Courts have long interpreted the Eighth Amendment’s guarantee against cruel and unusual punishment to mean that prisons must provide “adequate” and “medically necessary” care. Over the past 20 years, transgender prisoners have argued in lawsuits that gender-affirming hormone therapy and surgery should qualify. So should, they say, the ability to live according to their gender identity, what is known as social transitioning—to access the same clothes and cosmetics as people locked up in women’s prisons and grow out their hair just as other women prisoners do. States, balking at the cost or controversy of these treatments for their prison systems, have often fought these requests. In 2006, Wisconsin passed a bill barring prison doctors from providing hormones or surgery to trans prisoners; a federal court eventually struck down the law, concluding that it violates prisoners’ constitutionally protected right to medical care. Elected officials in Massachusetts tried but failed to pass similar legislation in 2009.

Trans rights and prisoners’ rights are points of tension in America’s culture wars and lightning rods in the political sphere. When Keohane’s case landed on the desk of Judge Mark E. Walker, however, he was charged with answering questions that fall in the realm of medical science and legal obligation: Had the state provided the medically necessary treatments for her diagnosed gender dysphoria, or had it knowingly failed to do so?

Shortly after Keohane filed her suit, the Florida Department of Corrections resumed her hormone treatment but still refused to allow her to dress or groom herself as a woman. These accommodations were important enough to Keohane that she pressed forward with her case. For the proceedings, she would have to be evaluated by mental health providers—her own and the state’s.

On January 3, 2017, Keohane was brought into a small windowless room at the prison to be interviewed by the state’s expert. An older man, bespectacled and balding, stood waiting to greet her. He introduced himself as Stephen Levine. Facing Keohane in a chair across the room, Levine, a psychiatrist, started his examination. First he asked the standard queries about her early experiences with gender dysphoria. Then he peppered her with questions about her sex life, she says, including details on how she masturbated and whether she enjoyed BDSM. It’s not unusual for clinicians to ask about sexual development and practices, but Keohane had been evaluated for gender dysphoria before and tells me she had never encountered someone so fixated on her sex life.

After the interview was over, Keohane’s mind started racing. She’d read a lot about trans history and knew that psychiatrists had played a significant role justifying the denial of treatment. As the weeks passed and she waited for Levine’s report, Keohane’s anxiety grew. “He’s going to make this all out to be some kind of really weird sex thing,” she worried. That was the worst-case scenario.

Stephen Levine was born in 1942 in Pittsburgh. He wanted to be a doctor from the time he was a little boy; he saw how much his parents and people in his community respected the profession. At Case Western Reserve University School of Medicine, he decided to go into psychiatry, drawn to how the field explored human stories as well as biology. In 1973, as he was wrapping up his residency, Levine heard that his alma mater was looking to hire someone to develop a medical school curriculum in human sexuality. Levine got the job. Over the next few years, he helped establish several clinics focused on sexual disorders at the university. In 1974, he cofounded Case Western’s Gender Identity Clinic to treat people unable or unwilling to live as the gender they were assigned at birth.

In the 1970s, when Levine entered the field, scientists and physicians had spent years arguing about what “caused” transness—and thus how to treat it. As Joanne Meyerowitz describes in her 2002 book How Sex Changed, from the mid-20th century on, two schools of thought competed for primacy. The first saw the desire to change one’s body through a psychoanalytic lens, as symptomatic of an unresolved early-life trauma or sexual difficulty. Initially, most psychiatrists belonged in this group, believing that physicians who helped their patients to physically transition only enabled their delusions. The attitude was summed up in the words of prominent sexologist David Cauldwell, who wrote in 1949, “It would be criminal for any surgeon to mutilate a pair of healthy breasts.”

The second camp emphasized biological factors. While its adherents generally agreed that a patient’s upbringing and environment could affect their gender identity, they considered a person’s chromosomal or hormonal makeup to be more important. Prominent figures, including the endocrinologist Harry Benjamin, pointed out that “curing” transness through talk therapy was almost always unsuccessful, in which case he favored a different intervention: “If it is evident that the psyche cannot be brought into sufficient harmony with the soma, then and only then is it essential to consider the reverse procedure.”

As these camps emerged, some trans people continually pushed back against their perspectives, insisting that transness wasn’t a medical disorder and that access to hormones and surgery shouldn’t be predicataed on the approval of mostly cis and male doctors. In the late 60s and early 70s, some trans people attempted to organize their own treatment clinics, by providing peer counseling and support and referrals for surgery.

Yet these clinics did not survive, and the primary of the medical model continued to take hold. In his research and scholarly work, Levine leaned into the psychoanalytic approach, theorizing that the desire to transition was a way for his patients to “avoid painful intrapsychic problems.” He explored what he considered potential causes of these feelings, including “an overly long, excessively symbiotic” maternal relationship. When a person declared themselves transgender, he liked to say, it was the mind’s attempt to offer them a solution. In psychotherapy, patients could interrogate and resolve the problem that brought these feelings into being. As in other clinics across the country at the time, Case Western’s offered surgery to just a few transgender patients—about 10 percent as of 1981. Many trans people were frustrated by this approach, but at least they found a degree of sympathy and understanding at clinics like Levine’s. They were seen as people who needed treatment rather than as deviants.

Through the ’70s and ’80s, Levine’s stature grew. His clinic attracted patients and he published articles in prestigious journals. By the early 1990s, however, the scientific consensus among trans health care providers and researchers was starting to shift away from psychoanalytic theories. More people were seeing evidence of in-born, biological factors. A growing proportion of providers argued—with ever-growing quantitative data to substantiate their claim—that medical interventions were more effective than therapy in alleviating gender dysphoria. One area of the human brain connected to sexual behavior is larger in men than in women. In 1995, a landmark study published in Nature found that this area was the same size in trans women as in their cisgender peers, regardless of their sexual orientation or whether they had taken hormones. The finding suggested that “gender identity develops as a result of an interaction between the developing brain and sex hormones.”

Two years after the Nature study came out, Levine was named chair of a committee of the Harry Benjamin International Gender Dysphoria Association, the nation’s primary organization for medical providers who treat trans people. The organization’s most important role was developing and publishing a regularly updated document that outlines the best practices for diagnosing and treating trans people, called the Standards of Care. Levine was invited to lead the team producing the next update, the SOC 5.

Revising the standards was a years-long process. In 1997 the organization held its biannual conference in Vancouver, British Columbia. Jamison Green, a trans man and a health activist then living in San Francisco, arrived at the event to find he was one of only a few trans people in attendance. It “wasn’t a welcoming environment,” he tells me. “They weren't happy to see you.” Levine was due to lead a Saturday afternoon session on the proposed draft of the standards. Green was sitting in the auditorium, waiting for the event to begin, when he heard a commotion outside. Technically, the meeting was open to members of the public, but there was a costly registration fee. Many other trans activists, especially the ones who lived locally, were outraged that, because of the hefty price, they were essentially being excluded from a meeting that would directly affect their care. They “started pounding on the doors and demanding to be let in,” Green says.

After a brief stand-off, the organization’s leadership agreed to open the doors. When they did, they ushered in a striking change. Trans people were demanding a greater say in the rules that governed transition-related care. In 2001, when the organization met in Galveston, Texas, Green noticed a difference. After he presented his research on how patients can be harmed when health professionals put their names in quotation marks or refer to them by the wrong pronouns, other presenters started to cross out what they’d written on their overhead slides and corrected their language. “It was a turning point,” he says. Medical providers “were starting to get it, that we were not just objects of study.”

The 2001 conference was a turning point for Levine as well. He saw the influence of trans patients and activists as veering the professional organization away from its intended purpose. “Advocacy meant that science was secondary to these poor, suffering people needing to have exactly what they want,” he says. Shortly after the Galveston meeting, Levine decided to cut ties with the organization.

About a month after she met with Levine, Keohane was called to pick up a letter. It was from her attorney; in the envelope, she found Levine’s evaluation. As she flipped through the pages, she saw her worst fears in writing. Levine had suggested that a deviant sexual impulse was driving her desire to transition. He wrote that she had “sublimated what was, for a number of years, overt sexual masochism into a long-suffering non-sexual adaptation.” Gender dysphoria is a psychiatric condition, he insisted, not a medical one. Having longer hair and access to women’s undergarments would likely help Keohane feel better, he acknowledged, but he went on to add that “there is nothing medically necessary about hair length. Women have short hair!” The psychiatrist proposed a semantic swap: “I suggest replacing the term medically necessary with psychologically helpful or psychologically pleasing would help all concerned to see the matter at hand more clearly.”

To Keohane the problem was obvious: Levine still viewed gender dysphoria through a psychoanalytic lens rather than as the product of neurobiology. She felt Levine was trivializing the harm of being forced to present as a man. Growing her hair was one important step in social transition. Private insurance, for example, will often cover the costs of wigs for women undergoing chemotherapy. Levine and the prison system just didn’t “want to consider me by the same standard as other women,” she says.

As Keohane and her attorney researched the psychiatrist’s history, they learned that Levine had evaluated a number of trans prisoners—including one of the first to file a lawsuit seeking gender confirmation surgery. In 2000, Michelle Kosilek sued the prison in Massachusetts where she was incarcerated. In 2006 the court asked the parties to submit names of potential experts. Both Kosilek and the prison system listed Levine. When he evaluated Kosilek, Levine backed the state’s position: Surgery wasn’t necessary to meet the standard of adequate care.

After the Kosilek case, other prison systems started calling on Levine. The Massachusetts Department of Corrections asked him to reevaluate 12 prisoners who had requested gender confirmation surgery; the health clinic the state used to provide care for trans prisoners had recommended surgery for all of them. “The Department of Corrections was outraged” by this, Levine told me. Levine recommended against surgery for all of them, though he says he laid out treatment plans that could lead to surgery in the future. “I think her [Gender Identity Disorder] is a product of her horrendous childhood,” he wrote in his 2011 evaluation of one Massachusetts prisoner. Surgery would not undo the consequences of her abuse and might cause “profound harm.” Over the next many years, Levine got calls from correctional systems in Virginia, California, New Jersey, Washington, and Florida to evaluate trans prisoners. Danny Waxwing, a trans attorney with Disability Rights Washington who represents prisoners, read Levine’s evaluations of his clients. “They were so shocking,” Waxwing told me. In one evaluation I reviewed, Levine characterized one prisoner’s sexual abuse as “pleasing”; the abuse had started when the prisoner was just 3 years old and lasted until they were 11.

Levine wasn’t altogether opposed to surgery, and he occasionally wrote letters in support of a patient’s request. But he believed it was misleading—and potentially dangerous—to suggest the procedure was medically necessary in the same sense as other necessary surgeries, like an appendectomy. If transness was the “solution” to a psychological issue, he claimed, surgery might ameliorate someone’s immediate suffering, but it wouldn’t address the root cause.

At the same time that Levine was making his mark as the go-to expert for prison systems, his peers began to publicly affirm that the medical consensus on trans care had changed. In 2008 the American Medical Association and the American Psychological Association issued statements affirming the medical necessity of hormones and surgery and calling on private and public insurers to cover the treatments. Doctors were adopting a “triadic care” protocol: First a patient spends time living in the world according to their gender identity; those whose symptoms are not resolved through social transition then advance to hormone treatment; if those two steps do not resolve the gender dysphoria, then they become eligible for gender confirmation surgery.

Scientists have also continued to explore possible genetic roots that may give rise to gender dysphoria. In a small 2013 study of pairs of twins, one or both of whom were transgender, researchers at the University of Hawaii at Manoa found identical twins were far more likely than fraternal twins to both identify as transgender: 33 percent versus 4.8 percent in twins assigned male at birth, and 23 percent versus 0 percent in pairs assigned female at birth. This was an intriguing indication that transness has genetic roots. In 2017, a study at New York’s Albany Medical College suggested a potential connection between differing levels of exposure to hormones in utero and gender dysphoria. And last year, researchers at the Medical College of Georgia at Augusta University found, in a study of 30 trans men and trans women, evidence that genetic variation in how our bodies process estrogen might contribute to a sense of gender incongruence. While far from conclusive, a growing corpus of work is exploring a biological basis for transness.

In May 2014, a Medicare board reversed a long-standing ban on coverage for gender confirmation surgery, pointing to the “consensus among researchers and mainstream medical organizations that transsexual surgery is an effective, safe, and medically necessary treatment for transsexualism.” The most recent version of the Standards of Care allows patients more agency and flexibility in the transition process and stress that being transgender is “not pathology.” That document explicitly applies to people living in prison.

At first, it seemed the courts would recognize this evolving consensus. In September 2012, a district judge found Kosilek’s Eighth Amendment rights had been violated and ordered the Massachusetts Department of Corrections to provide her with surgery. The ruling was upheld on appeal by a three-judge panel. But then, in December 2014, Kosilek was dealt a blow: The First Circuit Court of Appeals, meeting in its entirety, reversed the initial decision. Citing Levine’s testimony, the full court held that in providing Kosilek with hormones, women’s clothing and hygiene items, and facial hair removal, the Massachusetts Department of Corrections had done enough to meet the Eighth Amendment standard. Surgery, the court ruled, wasn’t a necessary next step. Joseph Sulman, the attorney who represented Kosilek at the time, says that Levine’s testimony was “everything” in this decision.

As long as scientists and medical experts have sought to classify those who don’t adhere to gendered norms, trans people have engaged with and challenged these efforts. For decades, activists protested the inclusion of “gender identity disorder” in the Diagnostic and Statistical Manual of Mental Disorders. The term “disorder” was stigmatizing, they argued. (The diagnosis was renamed gender dysphoria in 2013, when a new DSM version was published.) Some trans people have welcomed research on the biological roots of transness, but others view that research with suspicion, suggesting it continues to identify transness as an abnormality or aberration. Either way of looking at transness could be framed as pathologizing. Yet for trans people who want to undergo medical transition, these frameworks are also inescapable: Obtaining hormones or surgery inevitably requires a diagnosis. When trans prisoners make Eighth Amendment claims to get hormones or surgery or to transition socially, the “cause” of a person’s transness can become part of deciding whether treatment is medically necessary.

Keohane knew she wasn’t going to like what Levine had to say on that score in court, but she steeled herself. At 3 am on July 19, 2017, Keohane was awoken by guards. At 6 am they loaded her into a van for the hour-long drive to a federal courtroom in Tallahassee for the first day of testimony. Exhausted, she sat next to Tilley and her other attorneys. Her parents sat just behind her. When she was called to the stand, Keohane talked about the hopelessness that had driven her to attempt suicide. “There was no way I could possibly face as long as 15 more years being forced to live as something similar to male.” The medical expert hired by the ACLU told the court that he’d evaluated Keohane and determined that social transition was medically necessary.

The next day, Levine took the stand. He described Keohane as a “tragic person” whose “transgenderism is tied very much up to her narcissistic character, her demanding character, her sense of superiority.” He acknowledged that the ability to transition socially might be pleasing to Keohane but added, “The word ‘medical’ in a professional context has to do with the body. It’s physiology and it’s anatomy.” Keohane’s gender dysphoria, he suggested, had psychological roots.

On cross examination, Leslie Cooper, one of the ACLU lawyers, asked Levine about testimony he’d given earlier in a deposition. “You’ve opined that if she is unable to get access to the hair and clothing she’s seeking, she could be vulnerable to acute decompensation?” she asked, referring to a term for a steep decline in mental health. He answered simply: “Yes.”

More than a year after the trial ended, in August 2018, the lieutenant charged with overseeing Keohane’s dorm pulled her aside, and, as Keohane recalls, told her, “You won your case.”

On a spring day in April 2020, just as the Covid-19 pandemic was starting to rage, I called Levine on FaceTime. After a ring or two, he picked up. He was at his home outside of Cleveland, a slight, bald man in a black sweater and round-rimmed glasses.

Levine has a firm manner and an impressive memory. I asked him how he’d become an expert for prison systems, and he told me about the letter he received from the judge in the Kosilek case in 2006. The judge wrote that he was seeking a medical expert for a case that had “profound human consequences and may be valuable to the development of the law concerning transsexual prisoners.” The potential stakes of the case drew him in. The judge “appealed to my narcissism, and I couldn’t say no,” he told me. Soon, lawyers employed by corrections departments across the country were reading the Kosilek case testimony. Levine became a sought-after expert.

Levine still holds his position as a clinical professor of psychiatry at Case Western and spends the majority of his time treating people in his local community. He continues to evaluate prisoners for state corrections departments. For years he has served as the gender dysphoria consultant for the Massachusetts Department of Corrections. He still plays a major role in the state determining whether to approve or deny trans prisoners’ requests for transition-related medical care.

He also provides training to prison staff in transgender care. In a PowerPoint presentation to correctional staff in Idaho in 2016, Levine described the latest professional Standards of Care for trans people as “politics masquerading as science” and in another slide suggested that gender confirmation surgery ought to be conceived not as “life-saving … but as life-enhancing, as is providing augmentation for women distressed about their small breasts.” By then, every major medical association had issued statements in support of the standards and the medical necessity of surgery.

When I asked him about his status as an outsider in his professional community, Levine grew animated. I had it the wrong way around. The mainstream medical establishment, not he, had moved to the fringe. Groups that have endorsed the standards, such as the American Psychiatric Association, did so “on the basis of civil rights” rather than scientific evidence, he said. It was to the detriment, not the benefit, of trans people to presume that transitioning in any form was the best sort of treatment, he added. While noting that he believed the existing body of science was still limited, he cited studies indicating that trans people who’ve undergone medical transition still have poorer life outcomes than the general population, including higher rates of suicide and unemployment.

Many experts attribute this gap in life outcomes to the transphobia people face in almost every area of their lives, both pre and post transition. According to the National Center for Transgender Employment, for example, more than one fourth of trans people have lost a job due to anti-trans bias and more than three fourths have experienced workplace discrimination. But when I suggested this causal relationship as a possibility, Levine disagreed. “The advocates say there’s nothing inherently wrong with someone who wants to change their gender,” he said, but that’s “not what I see when I take care of these people.” When someone declares a transgender identity “thoughtlessly,” he told me, life doesn’t only get more difficult because of discrimination. “It’s also because one of the things that stabilizes human beings throughout our life is a loving, secure relationship with another person,” he said. “The pool of people who are available to love and abide by, not simply have sex with on a weekend, but who will connect with and stay with a trans person, the pool is very low.” (I know many trans people in loving committed relationships, including my partner.)

Levine has suggested that some prisoners come to a trans identity in hopes it will grant them an escape from the moral opprobrium of their crimes, some of which are brutal and violent. Sexual reassignment surgery “represents starting life anew without aggression,” he wrote in an evaluation of one California prisoner in 2015. “A rebirth cleans their internal moral slate.” Levine told me that he sees trans populations inside and outside of prisons as fundamentally different. “The people I see in the community haven’t raped, and they haven’t murdered.”

Randi Ettner, the psychologist who heads the medical organization for transgender health providers, has evaluated many of the same prisoners as Levine. “As medical providers, we treat medical conditions the same whether a patient has gotten a parking ticket or committed a murder,” she told me, whether the diagnosis is diabetes or gender dysphoria. Over the course of her career, Ettner says, she has visited around 50 correctional facilities across the country and has seen prisoners with severe gender dysphoria who are denied treatment. She says generally their mental health deteriorates, they attempt self-surgery, and sometimes they attempt suicide.

That was the story of Michelle Angelina, a trans woman incarcerated in New Jersey who was denied surgery after Levine evaluated her. In the years that followed, she severed her scrotum from her body and later took a razor to her penis and tied it off with a shoelace. Only after this second self-surgery did the state corrections department agree to have her operated on by a gender confirmation surgery specialist.

This spring, Levine and I talked again by FaceTime. I asked him if he felt responsible for what had happened to Angelina. He rejected this idea, pointing out that she had a complicated disciplinary and psychiatric history. Angelina was locked up for the brutal 2002 murder of a sex worker and continued to have violent outbursts for years behind bars. Levine viewed Angelina’s psychiatric problems and her gender dysphoria through the same lens. She’d attempted self-surgery because of her mental illness, not because she was being denied medically necessary care. “The fact that that person castrated himself [sic], if that’s what he did, is not that surprising, but self-castration in a person like that does not change policy—that is a disordered mind.” I could see Levine’s body tensing. “Don’t make me out to be some kind of bastard who’s withholding treatment from these long-suffering trans people,” he said. “I’ll be very disappointed if in reading your article there is not an appreciation for the human complexity here.”

A professional peer who knew Levine from their days at the Harry Benjamin International Gender Dysphoria Association told me that he found it bewildering to see his expertise leveraged by prison systems to deny treatment to trans patients. “I respected him a great deal. I learned a lot from him,” this colleague said. “But early on I thought that his views were affected from a very negative experience with a patient.”

One of the first patients that Levine treated at the Case Western gender identity clinic was a trans woman who eventually went by the name Ruth. Several years after Ruth came to the clinic, Levine approved her for surgery. About seven years later—after a series of emotional ups and downs post-recovery—she died by suicide. The former colleague, who asked that his name be withheld, says that from conversations with Levine he understood that the psychiatrist blamed himself for Ruth’s death. When I asked Levine about this, he said it was possible that her suicide had influenced his views but had not, he insisted, marred his professional opinion. He stressed that he has recommended other trans patients for surgery since. Yes, Levine said, Ruth’s death had introduced him to the stakes. “But why shouldn’t a doctor be careful?”

Michelle Kosilek, the Massachusetts prisoner whose 2006 lawsuit launched Levine as an expert witness, learned about Ruth’s suicide when the psychiatrist was asked about it during a deposition in her case. “If I could speak to Levine, I would remind him … that he knew at one time that when we are denied access to treatment that can make us whole … we experience an oppression of our being that few who are not so afflicted can truly understand or appreciate.”

Kosilek may soon be the first transgender prisoner in Massachusetts to get gender confirmation surgery while in custody. In April 2020, the members of the Gender Dysphoria Committee—including Levine—finally gave their approval. “Concepts about transgender have been changing dramatically, very quickly,” he told me about the committee’s change of heart. Then he added that he wasn’t permitted to comment on an individual case.

Keohane was thrilled that her Eighth Amendment claims had won the day. The federal court judge had come to the conclusion that she would suffer emotional harm without hormones and social transition. “It was an enormous relief,” she says.

But the relief wouldn’t last long. In March 2020, a prison psychologist visited Keohane in her cell. He had bad news: The Eleventh Circuit Court of Appeals had reversed the district court judge’s decision. The court lambasted the notion that the “Constitution should be read to require prison officials to provide every convicted inmate—at taxpayer expense—with any treatment that is ‘psychologically pleasing.’” The psychologist asked Keohane if she was suicidal and reassured her that, reversal or not, the prison wouldn’t take away her clothing or shave her head.

Levine’s words played a “decisive” role in the reversal, says Tilley, Keohane’s attorney—the court even used the “psychologically pleasing” language from his testimony. In the past 15 years, three circuit courts, all citing Levine, have ruled that transition-related care wasn’t medically necessary. Not all courts have found Levine’s evaluations to be persuasive: In 2015, a California judge found “serious weaknesses in Levine’s report that undermined his credibility as an expert” and ruled that a trans prisoner was entitled to obtain surgery, and in 2018 a district court judge in an Idaho case similarly gave “virtually no weight” to Levine’s opinions. With appeals courts in disagreement about the medical necessity of gender confirmation surgery, it’s possible the Supreme Court could take up this issue in the future. If it does, Levine’s testimony will undoubtedly be on the table.

In recent years, Levine also has become an expert in other cases and bills involving gender nonconforming people. In Idaho, he submitted an affidavit in support of bills that would ban trans youth from playing on the sports teams that match their identity; in Washington, he’s serving as an expert witness in support of litigation to overturn the state’s ban on conversion therapy; he testified in a British high-court case to limit trans kids’ access to gender-affirming care. One of the downsides of the Kosilek case, says Joseph Sulman, Kosilek’s former attorney, “was bringing Dr. Levine into the legal world and giving him a stamp of approval as a court-appointed expert.”

Today, the Florida Department of Corrections has a policy that explicitly permits trans people to dress in accordance with their gender identity. Keohane says that half a dozen trans women who are behind bars in Florida—women who’ve benefited from the change—have reached out to thank her for her efforts. She’s glad for her commissary items and the chance to grow her hair long. But it’s a tentative grip. She knows that those are privileges that can be taken away.

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