Transgender Jewish Educator Shares Her Rebirth in Torah

Chana Rosenson first saw Yiscah Smith from across the room at the Conservative Yeshiva in Jerusalem, where Smith was teaching and Rosenson was spending a year visiting as a rabbinical student.

Something about Smith struck Rosenson. She turned to a friend and said, “I don’t know who she is, but whatever she’s got I need to get for my soul.”

Smith soon became Rosenson’s teacher and mentor, and on a recent late-June evening she sat in Rosenson’s living room in Calabasas to lead a class on Chasidic wisdom and Jewish text. There was no institutional sponsor or promotional message for the event. Instead, Rosenson explained to her guests, “I just wanted to share her with as many people as I possibly could.”

Just over 25 years ago, when Yiscah Smith was still Jeffrey “Yaakov” Smith, with a long beard and six children, she left a life as a Chabad educator in Jerusalem. After 10 years living a secular life in the United States, Smith returned to religious life as an observant transgender woman and a nondenominational Jewish educator.

At the recent gathering at Rosenson’s home, Smith sat in front of a semicircle of about a dozen people from various L.A.-area neighborhoods and congregations, wearing an ankle-length blue dress that matched her eyes, her dark hair falling to her shoulders. For two hours, she wove together Torah passages, Chasidic teachings and her own personal journey in a lesson that was part Torah study and part self-help seminar.

“Authenticity is a process,” she said. “Trust the process — that God does not want you to live anybody else’s life.”

Underscoring her sermon was the idea that making peace with oneself is a prerequisite for fully understanding Jewish wisdom.

“God, Torah and the truth are aligned only when one is honest with oneself,” she said.

Smith came by that lesson the hard way. In an interview shortly before her lecture, she spoke with the Journal about her personal journey.

Jeffrey Smith grew up in a nonobservant Jewish household in New York. After visiting Israel for the first time as a college student in 1971, Smith became inexorably attracted to Jewish spirituality.

“I began to encounter my soul, and I really, passionately wanted to inquire more and practice more,” she told the Journal.

But she had known from early childhood that she identified more as a female than as a male. Delving deeper into traditional Judaism, she faced a spiritual paradox, trapped between her gender identity and her religious one.

“The more I started to access that place of inner truth, the more I felt like a fraud,” she said.

Back in the United States and studying toward a master’s degree in Jewish education at the Jewish Theological Seminary in Manhattan, Smith soon discovered the Chabad Lubavitch movement and became a regular at its headquarters in Crown Heights, Brooklyn. Smith recoiled from the movement’s strict gender roles but was attracted to the community it provided.

“The day I put on a black fedora and long black coat, the day I stopped shaving my facial hair to grow out a beard was one of the saddest days I can remember,” Smith wrote in her 2014 book, “Forty Years in the Wilderness: My Journey to Authentic Living.” “I looked in the mirror and all I could think was, ‘What have I become?’ ”

Still living as a married man, Smith moved to Jerusalem but soon found she no longer could keep up the charade. She built a home “that outwardly looked like the model Orthodox Chasidic family,” regularly hosting dozens for Shabbat dinner. Meanwhile, Smith said she felt increasingly isolated and alienated as a woman living inside a man’s body.

“There was no place for a transgender,” she said. “There was no place for me to go to the rabbis and engage them in the narrative of, Where do I fit in as a woman who senses I’m in someone else’s body? Where does Jewish law identify me? Where do I sit — what side of the mechitzah? Who do I study with? Who do I dance with?”

Smith went through a divorce in 1991m moved to the United States, and spent a decade living a secular life, languishing without community or direction.

“I felt I had the key out of the prison, but I did not yet have the wherewithal to actually put it in the door and let myself out,” she said.

She was working as a barista at a Starbucks in Colorado Springs, Colo., in 2001 when her 50th birthday came around and she decided she’d hit her “spiritual rock bottom.”

“That was the day that I decided, ‘I can no longer breathe any more breath into someone else’s body,” she said. “I had no more energy left to live a lie.”

Smith resolved to live as the woman she’d always known she was. One of her first acts after beginning her transition was to light the Shabbat candles, an act traditionally reserved for women. Though Smith’s childhood home had been mostly secular, both her mother and grandmother had lit Shabbat candles.

“I didn’t even have to really think about it — where else do I begin but light the Shabbat lights?” she said.

After that, “it just all came back,” she said. “That’s the road I’ve been on since.”

For the past 16 years, Smith, 66, has made “a daily commitment” to “becoming faithful to my inner core, my inner self, the image of God.”

These days, Smith teaches Chasidic texts at the Pardes Institute of Jewish Studies and the Conservative Yeshiva in Jerusalem and lives in Nachlaot, a warren of cobblestone alleys with a large population of American expatriates.

Though she no longer defines as Orthodox, she observes Jewish law as best she can. She hopes to carve out a new understanding in halachah that will account for a transgender woman living a Torah lifestyle. Despite the challenge, she’s confident that hers is a winning battle.

“The halachah has a flexibility to it,” she said. “It’s like a rubber band. It stretches, it contracts, it expands, with time it moves. And I didn’t trust that process because I myself was so insecure. Now, I’m able to say, ‘The rabbis need to address what’s really going on.’ And if it means a different interpretation, if it means an addendum, then that’s what we do. The halachah is strong enough. It has weathered 3,400 years of changes.”