Eleven years ago, Jay Ladin *00 was a popular professor at Yeshiva University’s Stern College for Women in New York, a published poet, and a father of three. Ladin also was in constant agony over the thought of continuing to live as a man.

Since early childhood, Ladin tried “to be what people wanted me to be. I taught myself to be nice rather than good, to be accommodating rather than honest, to be male rather than female.” At preschool, “I tried to play with the girls — I saw them as my peer group. I didn’t understand why they were running away. That’s the first time I remember being aware that my sense of myself was at odds with the way people saw me.” By 8, Ladin had “devoted himself to passing as a boy” who soon “called himself a pacifist so that he wouldn’t have to fight” in the schoolyard and avoided participating in team games by taking on non-athletic roles.

The struggle continued for another four decades, even as Ladin married, earned a Ph.D. in American literature at Princeton, and built a career as a teacher and writer. Throughout, Ladin fought — and sometimes succumbed to — the impulse to dress as a woman and seek out women for close friendships. Being a man was a performance. “I had never lived a day, a moment, as my true self,” writes Ladin, who worked every day to overcome “the secret shame of presenting myself as someone I knew I wasn’t.”

Today, Jay is Joy. After going through a wrenching divorce and putting her job at Yeshiva — an Orthodox Jewish university — in jeopardy, Ladin is living as a woman, an “incredible miracle, something I never thought would happen,” she says. By sharing her story, she also has become an inspirational figure to LGBT Jews who are struggling to reconcile their religious faith with their identities.

In 2005, Ladin’s wife listened as her husband of 23 years explained a need to live as a woman. It was painful news. Despite the transformation, Ladin, then 45, hoped to remain married; for the next two years, the couple continued to live in their house in western Massachusetts — with their son and two daughters, then ages 11, 6, and 1 — as Ladin, while continuing to live as a man, gradually altered her appearance. They then divorced. Ladin recounts the experience in her 2012 memoir, Through the Door of Life: A Jewish Journey Between Genders.

In the book, Ladin suggests that the news should not have come as a surprise, explaining that the couple had first discussed Ladin’s transsexual feelings when the two were college sophomores. Ladin’s wife could accept the feelings but not any expression of them, Ladin writes. Suppressing those impulses led Ladin to contemplate suicide many times: “I felt that God, to spare my family the shame and pain of my transition, wanted me to die.”

When it became clear that Ladin would live as a woman, her wife was distraught. “You’ve destroyed four lives to walk around in a dress,” Ladin recalls her saying.

“My wife saw me as choosing self-mutilation over her, over the life we had painstakingly built up since we were teenagers, over our future, over our past, over the well-being of our children,” Ladin writes. “Day after day, I was forcing her to witness the slow erasure of the man she loved. The hair on my head got longer. My body hair disappeared. My voice and manner of speaking altered. I was destroying myself before her eyes for the sake of a game of dress-up. ‘It’s murder,’ she told me, ‘even though you will never be convicted.’”

Several months after Ladin’s book was published, Ladin’s ex-wife published her own memoir. Christine Benvenuto writes that she felt powerless, belittled, confused, and left without a way to live as a married couple. Their children’s experience of Ladin’s transformation and the parents’ breakup was “the ugliest and most painful aspect” of the story, she writes.

Ladin, still living with the family, started dressing in women’s clothing for short stints (though not in front of her family, Benvenuto writes) and began hormone therapy. She eventually rented a room in a house near her family but had to leave that dwelling and several others for financial reasons: “I didn’t have enough money to have a stable place.” She continued to teach at Yeshiva’s Stern College as a man; her finances were so precarious because of the pending divorce that she often served as an overnight volunteer at a New York City homeless shelter in order to have a place to sleep. At one point she received a summons from the sheriff and underwent an investigation after her wife filed a complaint stating that Ladin was a danger to one of their daughters. Ladin writes: “My gender identity crisis had destroyed my marriage, shattered my family, and turned me into an unwelcome stranger in my own home.”

Dana Bevan *73, a biopsychologist who is transgender and has written two books on the subject, says hiding one’s true identity for decades before coming out in middle age — as Bevan herself did — is common. “After the realization of being transgender at age 4 to 7, many transgender people go into the closet because of cultural rejection in school, work, and social relations,” she says. In Ladin’s case, her mother was supportive when, in 2007, she told her she was transgender, but her best friend abandoned her.

But when Ladin began going out in public as a woman — outlining her lips in red, clumsily clipping on earrings, putting birdseed in the feet of pantyhose to fashion breasts — she felt reborn, even as she struggled through “adolescence in middle age.” “Every time I put on skirt and blouse and makeup, I feel myself spreading out into my arms and legs, filling my body, shuddering from death to life,” Ladin writes. In her own book, Benvenuto remarks on how happy and energetic her husband appeared when preparing to leave the family home, though Ladin recalls feeling miserable at that moment. (Ladin declines to say whether she has had gender reassignment surgery: “Part of dealing with transgender people as people is giving them privacy, and in our culture, we don’t generally discuss our genitals in public.”)

There were many more hurdles ahead, but Ladin felt that at last she could live: “I had done it. I was out. I was free.”

In 2007, a few weeks after receiving tenure at Yeshiva, where Ladin had taught writing and American literature at the university’s Stern College for Women since 2003, she wrote to the dean and explained her transition. She was put on paid leave and was told not to return to campus — “the best-funded and most courteous form of discrimination imaginable,” Ladin writes in her memoir.

Yeshiva University is the oldest educational institution under Jewish auspices in the United States and the flagship school of modern Orthodox Judaism, which blends adherence to Jewish laws with a recognition of the modern world. Yeshiva’s undergraduates are mainly observant Jews who study the humanities and sciences as well as the Torah. The 1,000-plus women at Stern are required to follow a modest dress code, and many students are engaged to be married before they graduate.

Yeshiva is not the only religious institution to be challenged by transgender issues; there have been questions and legal clashes at Christian schools as well. At Azusa Pacific University in California, a theology professor who had taught for 15 years as a woman came out as a man in 2013 and was asked to leave; he and the school reached a confidential agreement. Also in California, a judge denied most claims in a lawsuit by a nursing student expelled from a Christian college after the school learned she had been born male. And a transgender student at George Fox University, a school with an “evangelical Quaker and Christian ethos” in Oregon, was denied his request to live in male housing and moved off campus. George Fox later released a policy statement saying the school would retain separate housing for men and women, but would provide private living spaces and restrooms for transgender students where possible. “A guiding consideration will always be ensuring that students remain connected to community,” the statement says.

Transgender people pose a problem for Orthodox Judaism, Ladin says, because gender is central to so many of its rituals — men and women sit separately in synagogue, for example. The Torah proscribes cross-dressing, and Ladin — who is not Orthodox but reads the Torah daily — points out that it is considered a sin for men to take female hormones. As these issues come to the fore, however, “Orthodox Judaism is in the middle of a slow but profound cultural shift,” Ladin says. Though not many communities are openly welcoming, a few are quietly accepting. There is a feeling that “even though this is a sin, we don’t push people out because of sins,” she says.

When Ladin revealed her transition to the dean at Yeshiva, she was told it was the school’s policy that a physically male person could not appear on campus in female clothing, and that students and parents wouldn’t be able to accept her. Students, however, were not as rigid as the dean might have thought. While Ladin was on leave, several of her former students learned of her situation and arranged a meeting with her off-campus. One told Ladin that while she was politically to the right, she was outraged that the professor had been barred from campus, Ladin recounts in her memoir. When Ladin met the group of students at a coffee shop, they said there was something they had to ask her: “Are men really as bad as they seem on dates?” “My devout, sheltered students could talk, laugh, and learn with a woman they knew had once been a man,” writes Ladin.

Ladin’s lawyers from Lambda Legal, a civil-rights organization that deals with issues affecting LGBTQ people, wrote to Yeshiva demanding that she be reinstated to teaching. The university agreed a few months later to let her return. (It did stipulate that she use the single-stall unisex bathrooms and adhere to a Yeshiva policy that prohibits teachers from discussing their personal lives with students.) Hayley Gorenberg ’87, the deputy legal director of Lambda Legal, points out that New York City’s laws specifically prohibit employment discrimination on the basis of gender identity. “Obviously the school had resistance and trepidation,” Gorenberg says. “We are thrilled it turned around and did the right thing. It is extremely telling that once she showed up on campus as Joy, her students didn’t have any problem. The sky didn’t fall.”

When Ladin walked onto Yeshiva’s midtown Manhattan campus in September 2008, a little over a year since she had been banned, she became the first openly transgender employee at an Orthodox Jewish institution. She also made the news — a story on page three of the New York Post headlined “YE-SHE-VA” said some at the university were “horrified” by her return as a woman. Several students publicly disagreed, one telling the paper, “This is a wonderful opportunity for the school to show students firsthand how you can respect and learn from someone who might be different from you.” But Rabbi Moshe Tendler, a professor of biology and Jewish medical ethics at Yeshiva, said Ladin was “not a woman. He’s a male with enlarged breasts.” He also pronounced her “in massive violation of Torah law, Torah ethics, and Torah morality.”

Ladin says she is glad Tendler’s comments were published: “Nobody talked about this before. Now they had to decide if this one voice represented them, and a lot of people said, ‘This is not how Orthodox Jews talk about another human being.’”

“It took a tremendous amount of courage” for Ladin to reveal to the Yeshiva administration that she was transgender, says Rachel Mesch, chair of the school’s Department of Languages, Literatures, and Cultures. “Yeshiva University is an extremely gendered place, but my sense is it’s dealt with very matter-of-factly, which speaks to her talents as an educator.”

Ladin’s highly publicized case may be helping to make the climate at Yeshiva more accepting. Since she returned to campus, a Facebook group launched for “Yeshiva University LGBTQ+ and Allies” and a Tolerance Club hosted a panel on campus about being gay in the modern Orthodox world. A Yeshiva student recently came out as bisexual in the student newspaper. Before doing so, she met with Ladin.

Since the publication of her memoir and her outing in the Post, Ladin has become a prominent figure in the Jewish community, though she is not well known beyond that circle. She has given more than 120 talks on transgender issues both to LGBT Jewish groups and heterosexual Jewish audiences. Skyler Clarke, a male transgender student from California, met her at a weekend retreat for LGBT Jewish youth: “She’s put herself at the intersection of these very difficult conversations about Judaism and transgenderism, and resisted the pressure to walk away. She’s continuing to struggle with the text and notions of God.”

“Joy is singular in this space and very much a courageous pioneer and an inspiration,” says Idit Klein, executive director of Keshet, an LGBT Jewish organization. At Temple Emunah in the Boston suburbs, a congregation affiliated with the Conservative stream of Judaism and where a handful of children and adults are transgender, a recent talk by Ladin left congregants “absolutely riveted — people were in tears,” says Rabbi David Lerner. “It is life-affirming and life-saving work Professor Ladin is doing by sharing her own narrative.”

These days, enrollment in her classes is half of what it was before she came out, says Ladin, who had been nominated for Professor of the Year by students in 2007. “No one has ever been rude or disrespectful. It’s probably hard to find a place that’s as safe to be a trans person because the idea of respect is embedded,” she says. “It’s not comfortable, but I’m as protected as anyone could be. But students do avoid me and feel uncomfortable. I can see it in their faces.”

Last year, Ladin published her seventh collection of poetry, Impersonation, which explores gender transition, and won a $25,000 creative-writing fellowship from the National Endowment for the Arts. Looking back on her transition with several years’ perspective, she describes it in the book’s author’s note as “a lifelong process combining shame with triumph, ecstasy with disappointment, the mundane humiliation of airport security screenings with the miraculous experience of incarnation and fully embodied love.”

Ladin is remarried — to Liz Denlinger, a curator at the New York Public Library — and continues to split her time between Manhattan and Massachusetts, where her children live, though her relationship with them is strained. “Two of my children have stopped talking to me. I’m down to one, my 12-year-old daughter,” who still calls her Daddy, she says. The fissure with her other children, now 16 and 21, is “unbearably painful.”

What brings her the most pride are her presentations about her experience: “Helping people understand is the most important teaching I do.” But her relationship to gender “still feels oddly unsettled. I still don’t fit into the gender binary.” She hopes for a future when the issues with which she grapples will not be so fraught with misunderstanding and fear. “Someday,” she says, “being transgender won’t be any different than any other way of being human.” 

Jennifer Altmann is an associate editor at PAW.