Abby Stein knows how to work a room. “How many of you have had a bar mitzvah?” she asks the audience at a session on the transgender Jewish community she led last winter at LimmudFest UK, the flagship celebration of Jewish education and culture held in Birmingham, England. Hands go up. “How many of you have had a bat mitzvah?” Other hands go up. “How many of you have had both?” Only Stein raises her hands and jokes: “As you know by now, I’m cooler than all of you!”

Stein, 28, is the first openly transgender woman who was raised Hasidic. Born into the Satmar community of Williamsburg, Brooklyn, she is a 10th-generation descendant of the Baal Shem Tov, the 18th-century Eastern European founder of the Hasidic movement. The sixth of 13 children and the eldest boy, Stein, by the age of 20, was ordained as a rabbi, married and had a son.

When she learned of the pregnancy, “Gender started punching me in the face,” she writes in her recent memoir, Becoming Eve: My Journey from Ultra-Orthodox Rabbi to Transgender Woman. She was no longer able to ignore the feeling she had experienced all her life—that she was a girl. After her son’s circumcision, she sequestered herself in a unisex bathroom at a mall, went online for the first time with a friend’s tablet and searched whether a boy could become a girl.

“I cried when I read the word ‘transgender,’ ” she says. “It was like being diagnosed. I found words to describe who I was.”
Stein left the community in 2012 and divorced a year later, with a joint custody agreement and visitation rights with her son, Duvid. In 2015, she came out as a woman privately to her father, then wrote a blog post that went viral. She has now transformed herself in ways beyond her physical appearance. She recorded the audiobook for her memoir—it was released this past April—and is working on a documentary about her life. She has been interviewed by numerous media outlets, from CNN to Elle magazine, and has thousands of followers on social media. Her Instagram (@abbychavastein) is filled with sensual, stylish poses from professional photoshoots and speaking engagements, a stunning contrast to her “before” photos in Hasidic garb, complete with beard, payes and fur shtreimel.

Stein has leaned into the publicity, using her voice for a host of causes. She raises support for awareness about LGBTQ issues, trans rights and those leaving ultra-Orthodoxy; she speaks out against anti-Semitism; fights for immigration equality and criminal justice reform; and advocates for better education in the Hasidic community. She served on the 2019 steering committee for the national Women’s March, which was controversial because of allegations of anti-Semitism among its founding leadership, and remains involved in the organization. She is a co-founder of Sacred Space at the Wing in Brooklyn, a multifaith forum for women, and hopes to continue writing books.

Most recently, she participated in numerous protests against racial injustice in the wake of George Floyd’s killing, including some organized by the New Sanctuary Coalition, which is made up of clergy from every religious background. She says she has re-embraced her rabbinic identity, realizing that clergy groups have the ability to impact change on the ground.

“It’s important to be out there not just as openly trans, not just as openly Jewish, but as an openly Jewish trans person,” she says of her activism. “It’s important for people to know I am who I am, and to make them comfortable with all that I am.”

Stein has given over 400 speeches at venues worldwide—more than half in the Jewish community. She spoke Yiddish almost exclusively until she was 20, also studying in Hebrew and Aramaic. Traces of her Yiddish accent still cause her to drop her “th”s (“dee” instead of “the”).

At the Limmud session in December, she was dressed in a fuzzy, glittery, cropped red sweater and slim black pants from a monthly POP Fit subscription. A slash of vivid lipstick almost always brightens her face: Her favorites are a hot-pink appropriately called “Eve” and a shade of red called “Lilith,” both from the Fempower Beauty line of cosmetics. Her clothing and makeup palettes of pinks and reds are self-admittedly stereotypical as well as a feel-good rebellion against the constricted male black-and-white world she grew up in.
“To embrace my femininity is an act of power,” she says.

She came “full circle” as an extra in Unorthodox, the popular Netflix show based on Deborah Feldman’s memoir that stars Israeli actress Shira Haas. For her scenes, Stein was asked to dress as a Hasidic woman, tichel (head covering), pearls and all, and that became a triggering experience.

“When I left the Hasidic community, my brain made one thing clear: If I wanted to avoid reliving my trauma, my gender and religious identities could not in any way be the same femininity and Judaism that I knew growing up,” she wrote in a post on Alma, an online publication for millennial Jewish women.

She was able to unpack her feelings about covering her hair for Unorthodox with the help of a progressive Muslim friend who chooses to cover her head. When a woman on the Unorthodox set suggested that she must be against women covering their hair, Stein responded: “I am against women being forced or even just obligated to cover their hair.” The show, she contends, is extremely accurate in its portrayal of the Satmar community.

From a young age, Stein had a rule-breaking, almost subversive side. Not knowing how to rebel against being raised as a boy, she questioned religious authority. “I had no faith in anything I was told; if every authority in my life told me I was a boy, and I knew I was a girl, how could I believe the rest of their claims?” she writes in her book. “If they were wrong about my gender, they could be wrong about God, too.”
Though she wasn’t forced to become a rabbi, she says she was “groomed from birth” to follow the traditional path to rabbinic ordination, which she ultimately received at the Vizhnitz kollel in Monsey, N.Y. Along the way, she immersed herself in the culture as a “survival technique” to escape her identity issues. She was transferred from yeshiva to yeshiva and, using religious arguments to make her points, was dubbed by yeshiva officials as “the kosher rebel.”

“I knew that one day I’d leave the community,” she writes in her book, “and I wanted to know exactly what I was rebelling against.”

“I like to shake things up,” she acknowledges later in an interview in her Upper West Side apartment in Manhattan. “It’s a way of changing things. Making trouble is actually helping. It would be very easy to stay in my bubble,” in the overlapping communities of ex-Hasids, LGBTQ people and Romemu, a Jewish Renewal synagogue in Manhattan. “I’ve gotten enough attention without saying anything controversial ever again.” But, she adds, it’s a “responsibility and an opportunity to bring awareness and change.”

One topic that is off-limits is her son, in part because of a custody agreement that grants Stein’s former wife, Fraidy, the right to raise him Hasidic. “The only way I can make sure he has a better life than I did is to make some changes in the Hasidic community, and I think that has already happened,” she says. “No Hasidic child will grow up as I did where I didn’t know trans even existed. Because of what I did, people are talking about it whether they want to or not.”

She also won’t discuss her transition. Many people, she says, are only interested in the “exotic” aspects of her story: Have you had surgery? How do you have sex?

“I know people are curious, but tone down the exoticizing,” she advises. “Everyone’s experience is different. If you’re not sure if it’s O.K. to ask a question, ask yourself if you would ask it of a straight person. Unless I’m going to date you, it’s not any of your business.”
She describes herself as pansexual, meaning she is not limited in sexual choice and has dated people of all genders and people who don’t identify with any gender at all. “I care about the person, not their gender,” she says. She had a secret relationship with a male friend when she was in yeshiva. Today, she has a girlfriend, Brielle Rassler, a musician who is finishing her doctorate in clinical psychology and is also a rabbinical student at ALEPH: Alliance for Jewish Renewal’s ordination program.

Though Stein left the Hasidic community of her own volition, the island of Manhattan was as remote a world to her as a desert island. To find her way, she followed Footsteps, a Manhattan-based organization that helps people who leave the ultra-Orthodox world (a process dubbed “off the derech,” or OTD). The connection was lifesaving for Stein, who later helped jumpstart its Canadian counterpart, Forward. Footsteps, which counts over 30 percent of its 1,700 members as LGBTQ, taught her how to dress, talk to people of the opposite gender, eat out in restaurants and more. In 2014, she enrolled in Columbia University’s School of General Studies with scholarships, graduating with a degree in gender studies and political science.

Her parents cut her off financially when she told her father she was trans and no longer speak to her. Two of her siblings and a dozen of her 200 first cousins still maintain contact. Only the support of friends saved her from homelessness. Her apartment, which she rents and shares with a roommate, a trans man, is the first space she has lived in for more than a year since her college days at Columbia’s Bayit, a Jewish communal coop.

Her room is spare—bed, desk, bookcases crammed with Jewish titles, including The Bible Now, by biblical scholars Richard Elliott Friedman and Shawna Dolansky, and URJ Press’s The Torah: A Women’s Commentary, both of which she often pores over early on Shabbat mornings.
“I’m addicted to my books,” she says. A rainbow flag decorates the window. With a childlike eagerness, Stein shares her treasured objects: a stuffed Santa from her first non-Jewish friend; a few mugs from the 100-odd Hillels at which she has spoken; and a thick stack of boarding passes tied with a rubber band from her travels. Name badges from her speaking events dangle from hooks on the door. “To me, they are my biggest achievement,” she says of those talks. She has every magazine issue that has profiled her and opens them to show me. “I wish I had had the opportunity to see stories like these as a child. It’s very powerful, a strong proof of my work.”

Daniel, a transgender participant in a recent Footsteps conference at which Stein was a panelist, says that she was “the first trans person I knew existed and the first OTD person I was aware of. My first reaction was shock and horror. I couldn’t process it.” As he became aware of his own doubts about his gender and his religion, she became a source of hope and inspiration. “She is a true trailblazer,” says Daniel, who asked that his last name not be used. “She made the road map of what it means to be queer and OTD. Because she’s so vocal, she’s enabled me to find my voice, where before I was silenced. I never had a role model for any part of my existence.”

Part of Stein’s agenda is to motivate progressive communities, both Jewish and non-Jewish, to move from tolerance to celebration. “I like to say tolerance is meant for lactose or nuts, not for people,” she says. “When a teenager comes out to their parents, I don’t want the reaction to be, ‘I love you; I accept you,’ but rather, ‘This is so exciting! Let’s have a party.’ That is how we are taught to celebrate in Judaism. Go out of your way to show you want people not in spite of who they are but because of who they are.”

Stein celebrated her own combination bat mitzvah-coming out-naming ceremony in 2016 in her then-new Romemu community. Born Yisroel, the same name as the Baal Shem Tov, and nicknamed Sruli, she chose the name Abby Chava, which has biblical and familial connections but “doesn’t scream Hasidic.” A YouTube video shows her walking into the sanctuary to the song “Higaleh Na” (Reveal Yourself). She has posted the ritual she created with Romemu clergy on the TransTorah website, a collection of resources, books, texts, rituals and liturgy.

“I am struck by Abby’s kindness, her courage, her wisdom beyond her years, and her ever-evolving relationship with Torah,” says Rabbi Jessica Kate Meyer, a former co-rabbi and cantor at Romemu who is now part of the clergy team at The Kitchen, a Jewish religious start-up in San Francisco. “She has reached out to and cared for so many others, often at the expense of her own needs. Abby shares her boundless courage and light with those around her, and even those across the world who have read her words, or her story.”

Before she started transitioning, Stein battled depression and addiction to alcohol that had begun as a teenager and pills that started after oral surgery in 2013. She went sober during Hanukkah 2014, but the depression lingered. In addition to seeing a therapist, a simple ritual—lighting Friday night candles—helped to ground her, she says, forcing her to mark the week that ended and to do something to celebrate Shabbat. It became a mental health and spiritual practice. She now posts different pictures of herself lighting candles or at the Shabbat table on Instagram almost every week.

“My Judaism today is not remotely because of how I grew up,” she says. She no longer is Shabbat observant or kosher, but she loves Jewish holidays, Jewish texts, Jewish food—like latkes and schnitzel—and has visited Israel over a dozen times (her father and his family are Israeli).
“My family roots and heritage will always be a part of me,” she says. “Instead of fighting it I’m leaning into it and enjoying it. I love the power to pick and choose. Find what works, and whatever doesn’t—just let it go!”

What would the Baal Shem Tov say about his descendant? Stein doesn’t hesitate. “His message of unconditional love taught the equality of every person,” she says. “He would love me.”

Numbers and Resources

A 2016 study from the Williams Institute at UCLA, which focuses on sexual orientation and gender identity issues, found that just over half a percent of the adult population of the United States is transgender.

“No one knows how many transgender Jews there are,” says Rabbi Micah Buck-Yael, director of education and training for Keshet, a national organization that works for LGBTQ equality in Jewish life. “There are transgender Jews in every type of Jewish community, observing all types of Jewish practice and in all regions of the country, religious and secular, young and old, of all races, abilities and backgrounds.” Buck-Yael adds that a 2015 study by the National Center for Transgender Equality found that 19 percent of transgender people who had been part of a religious community left due to rejection, while 39 percent left because they feared rejection.

Other Jewish organizations that support LGBTQ individuals include Eshel, serving 300,000 Orthodox individuals and their families, and JQY, Jewish Queer Youth.

Rahel Musleah, a frequent contributor to Hadassah Magazine, runs Jewish tours to India and speaks about its communities.