How Hasidic rabbis helped an Orthodox father of six become true to herself

In 1991, Yiscah Smith left Israel as a Hasidic man. Exactly 20 years later, she returned to the Holy Land as an observant Jewish woman. Her radically different external changes were mirrored in her newfound spiritual contentment, Smith told The Times of Israel ahead of the Haifa Film Festival premiere of a documentary charting her journey.

Smith’s transition from male to female, and from a life of loneliness and confusion to one of authenticity and contentment, is chronicled in a film by Rachel Rusinek and Eyal Ben Moshe titled, “I Was Not Born A Mistake,” screening  on October 17. The documentary on Smith, a noted Jewish educator and spiritual mentor, will also air on Israel’s Yes Doco channel later this year and be screened at the New York Jewish Film Festival between January 15-28, 2020.

When The Times of Israel recently met the warm, grandmotherly Smith, it was hard to imagine her as a young, bearded Chabad scholar. The father of six was constantly fighting the pernicious effects of gender dysphoria that forced her to leave Israel and her family, and put a pause on her Jewish observance for over a decade.

“I left Torah observance when I left Israel. I felt there was no place for me in the Torah observant world because I was filled with these demons inside. I thought I was the only person suffering from this. I didn’t even know there was a name for it. It was just my reality of disconnection and loneliness,” the American-born Smith told The Times of Israel in an interview at her home, a small stone building with a large garden entrance in Jerusalem’s Nachlaot neighborhood.

Yiscah Smith (Yaakov) as a young Torah scholar and educator in the Old City of Jerusalem in the late 1980s-early 1990s. (Courtesy)

Smith came out as gay while living and working in the early 1990s in the Chabad community in the Jewish Quarter of Jerusalem’s Old City and was shunned and deprived of continued employment. She had no one she could talk to in an effort to sort out her feelings and did not realize she was actually transgender and not homosexual.

“I did not trust the rabbis. Because of my experience with them, I couldn’t really open up to them. And as much as I felt close to my mom, I couldn’t talk to her. I felt that whoever I could open up to would think that I was mentally challenged and would have me committed,” Smith said.

Even as a young child Smith, now 68, did not feel comfortable in her male body. “I used to lie in my bed when I was five, seven, 10 years old saying, ‘What’s wrong with me? I’m not connecting to anybody.’ I knew I didn’t belong with the boys. I want so much to always be with the other gender, but I knew I couldn’t be — not in the pink and blue world of the 1950s,” she said.

It took 50 years for Smith to fully come to terms with her gender dysphoria and embark on a gender transition process. It occurred gradually over the two decades she lived in the US before returning to Israel.

She refers to the process as a tikkun ruchani, a spiritual correction or repair. “The gender transition was the misgeret [framework] and the tikkun ruchani was the tochen [content],” she explained in her New York-accented Hebrew.

Smith draws upon the spiritual journey she has made to help others get better in touch with their “inner core being” and the “divine spark within.” She does this by teaching Judaism as a meditative, contemplative practice, using Hasidic texts as a jumping off point.

She is quick to emphasize that she is no longer associated with Chabad or any other Hasidic sect. When she uses the word hasidut (Hasidism), she does not refer to Hasidic Jews, but rather to “spiritual Torah.”

“What that means is to encounter the divine presence within a person, to encounter the spiritual center, to encounter the still small voice within. It’s something deeper inside oneself, rather than a theology believing a God out there,” she said. “It’s really making contact and touching that part of us that’s bigger than our ego and bigger than our limited place in time and space.”

From Jeffrey to Yiscah

Yiscah Smith when she was a young man named Jeffrey. (Courtesy)

Smith first visited Israel as a 20-year-old college student in the summer of 1971. She was then known as Jeffrey, and was studying education and sociology at The George Washington University. Inspired by the Israel visit, Smith took as many Jewish religion-related courses as possible upon her return to school. Immediately upon graduation, Smith married a young American woman she had met on her Israel trip.

On a return visit to Israel in 1974 to do preparatory Jewish text study for a graduate program at the Jewish Theological Seminary in New York, Smith started observing Shabbat.

She found her MA in Jewish Education program too much focused on a “worship of academia and lacking in spirituality,” making her ripe for her encounter with Chabad. “It really pulled me. It really spoke to my soul,” she said of the Hasidic movement’s outreach efforts.

By the time she graduated from JTS, she was fully part of the Chabad community in Crown Heights, Brooklyn and became known as Yaakov, the Hebrew name she was given as a baby. Contrary to what some have written about Smith, she never attended yeshiva full-time, nor did she receive rabbinic ordination. She supported her family by teaching, and continued to study as much as possible.

In 1977, Smith and her wife moved to Safed in Israel with their first child. The family moved back to New York in 1979 because their second child had a medical challenge that could be better treated in the US. Smith and her wife had four more children while living on Long Island, and then returned to Israel in 1985, settling in Jerusalem’s Old City. Smith worked in education and community outreach at the Chabad synagogue and community center there.

Yiscah Smith (right) when she was a Chabad educator named Yaakov speaking to the Chabad Rebbe Menachem Mendel Schneerson. (Courtesy)

After coming out as gay, divorcing her wife, and being shunned by Chabad colleagues, Smith left Israel in early 1992. Dropping all connections to an observant Jewish life, she reverted to calling herself Jeffrey and worked at a travel company specializing in Israel tourism.

“I didn’t find a place in the Jewish world and I missed it. I longed to have Shabbat again. I had loved learning Hasidut and spiritual Torah,” she said.

In 1997, Smith moved to San Francisco, and then moved to Colorado Springs a few years later. There, she started working for Starbucks, which  “not only had an incredible benefits package, but also a diversity policy that was part of the company’s core values.” This was fortunate, as it was at this point that Smith decided “to go into high gear” with her transition — including surgery and name change. While working for the company, she went into management training as Jeffrey and left it as Jessica (Yiscah is the Hebrew version of Jessica).

Smith, who transitioned at age 50, said she was fortunate not to have experienced transphobic threats or behavior. “I passed very easily very soon. People started ma’am-ing me instead of sir-ing me pretty quickly,” she said.

Smith left Colorado for Seattle in 2005 so that she could experiment with living as a woman in a city where nobody knew her. She continued to work for Starbucks for a while, and then went back into Jewish education before returning to Israel in 2011.

Yiscah Smith at her Jerusalem home, August 2019. (Renee Ghert-Zand/TOI)

“The first night in Seattle that I started lighting Shabbat candles was a very big moment for me. I really felt that God had guided my whole transition, because I had done it differently than anything else in my life,” she said.

For once, she had done things without running away or rushing, and by being present in the moment.

“It really created inner shifts in my whole personality. I am a very relaxed, calm, gentle soul now. That took years of practice. I don’t believe I’ve changed. I believe I was revealed the potential to be that once I was able to slay the dragons that had put me in a constant survival mode,” Smith explained.

The four fathers

Smith draws on wisdom she gleans from studying the lives and writings of rabbis she admires, such as the four whose photos she has displayed on a shelf in her living room: the Lubavitcher Rebbe Menachem Mendel Schneerson; Rabbi Abraham Isaac Kook (the first Ashkenazi chief rabbi in British Mandatory Palestine in the Land of Israel); Rabbi Shlomo Carlebach (“The Singing Rabbi”); and Rabbi Kalonymus Kalman Shapira (known as the Piaseczner Rebbe, and a victim of the Holocaust).

Photos of (from left) Rabbi Menachem Mendel Scheerson, Rabbi Abraham Isaac Kook, Rabbi Shlomo Carlebach, and Rabbi Kalonymus Kalman Shapira diplayed in Yiscah Smith’s living room, August 2019. (Renee Ghert-Zand/TOI)

Smith shares her spiritual approach to Judaism by teaching at Jerusalem’s Pardes Institute of Jewish Studies, podcasting on her “Authentic Jewish Living” website, mentoring individuals in person or virtually, and by speaking publicly around the world. She has also published a memoir, “Forty Years in the Wilderness.”

“Yiscah is a very deep thinker and she has unique way of bringing meditative practice and her personal narrative into text learning. She has awakened in me a profound interest in the text and has inspired me in terms of my own personal religious growth,” noted Rabbanit Nechama Goldman Barash, a scholar of rabbinic texts and halacha (Jewish law), who is one of Smith’s colleagues at Pardes.

It was the Hasidic masters who helped her come back to Judaism

“She doesn’t take a critical, academic approach to the text. You are learning it with her. She has you going in deep. This is the kind of learning that allowed her to transition. It was the Hasidic masters who helped her come back to Judaism,” Barash said.

Jason Gusdorf, a 26-year-old Georgetown University Medical School student, came away inspired from a class with Smith when he recently studied at Pardes. He said he was struck by how genuinely and “straight from the heart” she taught the material.

Inspired by how Smith had connected to her authentic self, Gusdorf started writing music a year ago. “Yiscah’s class helped me uncover what was inside me,” he said.

Others also perceive Smith’s calm, gentle focus. “Yiscah is inspired and inspiring. She brings fullness of heart and mind to every encounter and moment,” said Rabbi Ami Silver, one of Smith’s study partners in Jerusalem.

Smith said she never considered coming back to non-halachic Judaism. However, she does not see herself as part of any Jewish religious movement, but rather as a post-denominational Jew.

A woman, period.

In terms of the movement for LGBTQ rights, Smith said she is not particularly politically committed. She sees herself as pro-human rights and a spiritual activist more than anything else.

Despite being labeled by some as the grandmother of the Israeli transgender community, Smith refers to herself as a woman, and not a transgender woman. “I was born transgender, and for me, being transgender was the problem. My transition was the solution to the problem,” she explained.

American-born religious transgender Jew Yiscah Smith spoke to Mekudeshet participants on Journey 4 about her own search for truth (Jessica Steinberg/Times of Israel)

Smith also does not agree with lumping transgendered people together with lesbians, gays and bisexuals. She is supported in this by her friend and neighbor Sarah Weil, at whose marriage ceremony to another woman Smith officiated in 2017.

“Yiscah believes that trans is distinct, and I agree. Any intersectionality erases individual experiences. LGBT is not a value system. Judaism is Yiscah’s value system. She identifies with the Jewish community and universal human values. That is why so many people relate to her and are inspired by her,” Weil said.

Smith’s transition and spiritual return has moved her from a life of loneliness to one filled with friends, colleagues and students. Most importantly, it has brought her back in touch with some of her family members. She reconciled with her late mother, her father and one of her two sisters.

She is also reestablishing relationships with some of her children — none of whom are still part of the ultra-Orthodox community. It is difficult for Smith to think back on the bad parenting decisions she made, but she is making amends for them now.

“By not living an authentic life and being in a lot of pain, I put myself first at times. I wasn’t there for [my kids] in the way they needed. I really didn’t hear them,” Smith said.

“I still make mistakes, but they are not because I am running away from my truth. My children see that I am there for them now,” she said.