On a sunny Sunday afternoon in late April, a group of people gathered in a small house in Crown Heights, Brooklyn to listen to Yiscah Sara Smith read excerpts from her memoir.

The audience, mostly young adults of various Jewish denominations, as well as members of the LGBTQ community, listened enraptured as Smith spoke of her transition from life as a man to a woman.

Smith, 63, is a Jewish educator, author and spiritual mentor. She was born Jeffrey Scott Smith in Patchogue, New York, a small town on the South Shore of Long Island. She became religious as an adult and later joined the Chabad movement. She married and had six-children with her then-wife.

Smith’s journey began in 1971, when a young, 20-year-old Jeffrey visited Israel for the first time. As he stood in front of The Western Wall in Jerusalem, he was forced to decide between the men’s and women’s section. “I felt forced to choose,” she said at the event, “to announce to the world whether I was male or female.”

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Fifteen years ago, after a long struggle with gender dysphoria, she underwent gender reassignment surgery.

She now lives in Jerusalem as a woman, and prays regularly at the Western Wall. But this time in the women’s section, on the right side of the segregating partition.

Last month Smith toured the United States to promote her new memoir, "Forty Years in the Wilderness: My Journey to Authentic Living."

“It is the story of a man, facing his truth, embracing the woman she was always meant to be and returning to her faith with wholeness and authenticity,” she writes on her blog.

For Smith, it was not her first visit to Crown Heights’ Chabad enclave. The event was held just down the road from the house she lived in for a few years with her wife at the time, and the older of her six children.

For many years Smith identified as a Chabad hasid but suffered under the cloud of her gender dysphoria. She recalled fondly her meetings with Rabbi Schneerson, the grand rabbi of Lubavitch over 20 years ago, and said that she believes he knew about her internal suffering at the time, about her struggle to be true to herself as a woman in a man’s body.

“It wasn’t in what he said,” she said, “but what he didn’t say.”

Smith recalled one of her earliest memories of her gender dysphoria as a 5-year-old boy watching her mother put on makeup. When Smith’s mother suggested the child watch his father shaving instead “because you’re a boy,” she recalls beings confused and dismayed.

She recalled a later period as a teacher at an all-girls, orthodox school in Israel. “Think of the Irony!” she laughed. “They think I’m the only man and I’m not. It was a dream come true.”

After Smith’s marriage disintegrated, she stopped practicing observant Judaism. But she says it was also her search for a spiritual connection that led her to transition from Jeffrey to Yiscah. In her book she writes about her struggle with her religious beliefs, alongside her gender dysphoria.

Now, Smith identifies as an orthodox Jew and with the launch of her book she has become known as somewhat of a transgender activist in the orthodox community.

“It’s God who is talking,” she said at the event, “but I’m the mouthpiece.”

She says the reaction from the orthodox community hasn’t always been welcoming. “The Rabbis … have always been a beat behind society, and as society progresses faster, it’s three beats behind,” she said. Other members of the orthodox community have cut ties with her and provoked what she calls “verbal violence" with her.

But she has received a wealth of support from others. "I’ve been very pleasantly surprised that the majority of the religious people in Israel that I interact with, respect me for wanting to be honest with God," she said.

When an attendee questioned the possible contradiction between her journey and her faith, Smith said that the community needed to create space for everyone. "Everyone comes into the world needing to do a tikun," she said, using the Hebrew word for repair. "None of us come into the world perfect. So the challenge, is 'What is my tikun?' Your soul needs to achieve something it can only achieve with the combination of your soul and your body,” she said.

"I no longer live with secrets,” she said.

editor@jewishweek.org