As Caitlyn Jenner Dominates Discourse, Orthodox Jewish Woman Shares Own Trans Journey

Transgender woman Yiscah Smith’s journey was complicated by her Orthodox Jewish beliefs. Photo: Yiscah Smith

After a 40-year journey that started as a little boy, Yiscah Smith was finally ready to live as the woman she had always known she truly was. Much like the celebrated transgender woman of the moment, Caitlyn Jenner, she had always struggled for personal and wider acceptance. But unlike the celebrity’s transition, Smith’s trials were heightened by her Orthodox Jewish beliefs, and has led to a much more modest existence.

Yiscah Smith has had two seminal moments in her life, and both took place at the Western Wall in Jerusalem.

The first occurred in 1971, when the now 64-year-old Orthodox Jew stood in the men’s section of the gender-segregated holy site as Jeffrey Smith, the name and identity she was born with. The second was in 2011, a full 40 years later, after decades of soul-searching, a wrenching split from her family and a series of grueling surgeries to transform her body into that of a woman.

“There I was on the woman’s side at last, feeling everything I wanted to feel,” Smith says.

Transgender people have never been more visible in pop culture. From Bruce Jenner’s stunning coming-out cover as Caitlyn on Vanity Fair, to Laverne Cox’s soul-stirring, metafictional portrayal of Sophia Burset on the hit television show “Orange is the New Black,” Hollywood’s handling of gender dysphoria is proving to be, well, transformative.

For Smith, her coming out journey was never about raising awareness or amplifying a platform. If anything, it was about finding a place of sanctuary and quiet where she could be, in her own words, finally authentic.

“I was always wrestling with my own inner demons,” Smith says, seated in her cozy one-bedroom home in Jerusalem’s Nachlaot neighborhood. A cluster of ancient stone apartments, twisting back alleys and hushed green courtyards, Nachlaot is known as one of the most inclusive corners of the city, where seminary girls and tie-dyed hipsters stroll its cobblestones with equal frequency.

Born in Long Island to a secular Jewish family, Smith says she knew from the age of five that she was a woman trapped in a male body. This was long before the Internet made terms like “transgender,” “gender reassignment surgery” and “orchiectomy” accessible to anyone with a keyboard and a modem, and Smith’s story was at this point like a lot of people who identify as transgender: She was in hell, and she had no idea why.

“I knew I was suffering from this weird thing. I knew somehow that I was a girl, but I didn’t know how I knew it…. How could it be, I thought, that I was the only one who understood who I was, that even my mother was wrong?” she says.

At the age of 20, Smith—who had never been particularly religious—visited Israel for the first time. And it was here that her story started to veer down an unexpected path.

Drawn by the allure of the kibbutz movement, Israel’s famed socialist collectives, Smith bought a plane ticket to volunteer in the country for two months. On a day off, she visited Jerusalem, found her way to the Western Wall, and after wrestling with herself over which side of the gender barrier to stand on, walked up to the ancient parapet and rested her head against the stones.

This was the first moment in her life, she says, when she felt a sense of true belonging. Maybe, she thought to herself, religious observance would be the answer to the aching isolation she had been feeling for so long.

Smith—still living as Jeffrey—stayed in Israel and threw herself into the Orthodox Jewish world, adopting the black hat and strict dress code of religiously observant men, marrying an Orthodox Jewish woman, and eventually bearing no fewer than six children.

“I felt like Hashem was inviting me to be in a relationship with him,” Smith says, using a common Hebrew term for “God.” “It was the beginning of my transition without me even knowing it.”

Drawn in by the spirituality of religious Judaism and enamored with the scripture and history that are woven into observance, Smith convinced himself for a while that he could, in fact, live as a religiously observant man. But there was one major issue—the Orthodox Jewish world is wholly binary, with men and women segregated in nearly every social setting and quotidian daily tasks doled out based on gender alone. Sequestered among the men of his sect and fully dressing the part, he was further away from womanhood than ever been before.

“I didn’t realize what a gender-defined world I was going into,” Smith admits today. “I didn’t feel at all comfortable. I did with the women, but the men dress in such a definitive way—the beard, the hat, the long black coat. For me, it felt like one disguise after the next.”

She prayed, hard, for compassion. She prayed for something inside of her to change. But her prayer, she says, was like the age-old Jewish yearning for a messiah. It simply never came.

What happened in 1991 bore all the makings of a Jerusalem scandal: the Hasidic father of six sat down with his wife and family and said he was leaving them to go live as a gay man in Tel Aviv.

“Everything fell apart,” Smith says. “Divorce, breaking up my beautiful family, leaving Jerusalem, living a Torah way of life. I felt there was no place for me…it was a spiritual earthquake.”

Today, Smith hesitates when asked about her family. Her children, she says, took the news hard. She is closer to some of them than others. She declines to speak about her ex-wife.

After earthquakes, however, comes rebuilding. Smith wandered from Tel Aviv to New York to San Francisco, dating men and trying to live as a homosexual man. In each relationship, she says, she found herself being told she was too much of a woman. She was still on the outside, looking in.

“Not only had I given up my Jewish way of life, I didn’t connect to these gay guys,” she says. “Because I’m not gay. I’m a heterosexual woman. I felt as disconnected from them as I did on the men’s side of the [gender barrier].”

About 0.3 percent of people identify as transgender, but openly trans people experience significantly higher incidences of violence and prejudice than the broader LGBT community. In Israel, more than half the transgender population has reported experiencing some sort of hate crime, while crimes against the broader gay community are considered rare.

This week, the Tel Aviv Gay Pride Week and Gay Pride Parade is being held as a show of support toward the city’s transgender community, with the tagline “Tel Aviv Loves All Genders.” Smith is speaking at a symposium on gender issues and sexuality as part of the festivities.

In 1992, while reading a newspaper article, Smith saw the term “transgender” for the first time. It was, she says, like being handed a key out of prison.

“I had no more energy left to continue breathing life into someone else’s body,” she says. “My journey was as much a spiritual and healing one as it was of a gender transition.”

Today, Smith is back in Jerusalem and living a life typical of an Orthodox Jew, dressing in a modest fashion and praying—on the woman’s side of the gender divider—at a local synagogue. She serves as a spiritual advisor and educator, and has written a memoir, “40 Years in the Wilderness: My Journey to Authentic Living,” about her transition.

In 2011, 40 years to the week from the day she first visited the Western Wall, Smith returned to the site and walked to the woman’s side to pray. Her transformation, she says, was finally complete, and despite the fact that she was 60 years old at the time, it was one of the first moments in her life where she felt she was truly being honest about who she was.

As part of her journey, she’s become a counselor and advisor for people seeking authenticity in their lives, be they trans or straight, Jewish or gentile. For Avi Leeker, a recent immigrant to Israel who met Smith during a Jewish studies class in Seattle, and seeks her spiritual advice, her trans identity is irrelevant.

“I do not see Yiscah as a trans woman,” Leeker wrote in an email. “I see Yiscah simply as Yiscah.… Authenticity, truth, love, acceptance—these are the things you feel and experience in her presence, and you are inspired to try and achieve these attributes in yourself.”

Leeker points to Smith’s own personal journey and says it serves for him as a guide in living a more intimately Jewish life.

“The Torah teaches us, commands us in fact, that we are to love our fellow [man] like we love ourselves, and Yiscah is helping all of us understand with our hearts what we all know to be true in our heads: that you cannot truly love your fellow [man] until you love yourself,” he said.
That focus on knowing your inner self is a major piece of Smith’s message today.

She says she appreciates the progress transgender celebrities have made in creating more visibility for the community, but is less enthusiastic about the highly sexualized nature of more visible trans people, especially Caitlyn Jenner.

“She’s not a role model,” Smith says, “because she’s unreachable … I don’t think for 15-year-olds or 20-year-olds, hers is a healthy image. She can do whatever she wants and it’s her journey, and it may be authentic to her, but for most people, it’s not something they can aspire to.”

Smith, who dresses her tall, muscular frame in simple skirts and modest, colorful tops, says she prefers the idea of female modesty.

“I navigate the space of modesty the way I navigated my entire journey. Clothes are just a dimension of it,” she says. “Of course I believe your external matters, because if it didn’t, I wouldn’t have transitioned my body. But the message you send has to be done with sensitivity. I want to put out a message that is real. I don’t feel that’s what Caitlyn Jenner has done.”

But then Smith smiles. “She’s only at the beginning of her journey. Maybe in a year or two, she’ll change her style, and she’ll put out an image that feels more real.”