The Rabbi Who Chose Trans Orthodoxy

Shortly before the 1991 Gulf War, Rabbi Yaakov Smith, a father of six and an emissary of the Chabad Hasidic movement in the Old City of Jerusalem, hosted a Shabbat dinner. As the guests were leaving, one took Smith aside and said something that would reverberate with his host: “That was an amazing act you performed. Whatever is wrong, take care of yourself.” Fast forward thirty years and Yaakov has become Yiscah Smith, a transgender person who still lives and teaches in Jerusalem. Smith’s transformation is the subject of the documentary I Was Not Born a Mistake, created by the Israeli filmmakers Rachel Rusinek and Eyal Ben-Moshe. The film premiered at the Jerusalem Film Festival this past Hanukkah and made its U.S. debut in January.

I Was Not Born a Mistake is, on its face, a story of self-realization. Narrated almost entirely by Smith, and set to the backdrop of springy music and carefully selected photographs, it describes the long and winding journey of a person in search of an identity. Yaakov/Yiscah was born Jeffrey in 1951 into a secular Jewish home. In the 1970s, Smith travelled to Europe, making a chance stopover in Israel, which, in the film’s telling, ignited a spiritual awakening and a desire to explore Judaism.

Though the movie glosses over the next several years, Smith describes this period in detail in a 2014 memoir, Forty Years in the Wilderness: My Journey to Authentic Living. Stops included a kibbutz, the Jewish Theological Seminary in New York, and Safed, the Galilean city of mystics and artists. Smith was eventually drawn to Ḥasidism, and soon joined the Chabad-Lubavitch movement. Along this meandering path Smith married, fathered six children, and lived in the Crown Heights neighborhood of Brooklyn and later in Jerusalem’s Old City. Yet twenty years after beginning this journey toward religion, Smith abandoned Orthodoxy and embraced a secular gay lifestyle, severing ties with the wife and children who had faithfully accompanied him for many years.

Smith subsequently spent a long stretch in New York City and then California. After a former boyfriend commented on Smith’s feminine qualities, Smith gravitated toward transgenderism and began dressing and living as a woman. The film emphasizes how this embrace of a new “gender identity” dovetailed with a return to Jewish observance. The connection between these two most recent changes may strike viewers as contradictory. But Smith suggests that a person struggling with the relationship between inner and outer self may reflect upon the mystical relationship between body and soul as understood in Chabad Hasidism. Eventually Smith moved back to Jerusalem and now appears to the outside world as a put-together Orthodox woman, complete with wig and nail polish, ready to teach and inspire.

Despite the straightforward and sharp biblical prohibition of cross-dressing, Smith’s attempt to live as a woman involves an attempt to develop a theology of transgenderism. Smith draws on idiosyncratic interpretations of the kabbalistic idea of tikkun, or “repair,” to explain why even God’s own precious creations may require additional refinement and perfection. In traditional Jewish mysticism, tikkun proposes that human actions, prayers, thoughts, and speech can restore the cosmos to its prelapsarian state. Smith understands tikkun more as a course-correction or dramatic change. For instance, Smith dubiously reimagines God’s commandment to Abraham to circumcise himself and his sons as demonstrating that physical mutilation may sometimes be exactly what God wants, traditional Jewish prohibitions against such practices notwithstanding. In speaking engagements and one-on-one sessions, Smith urges listeners to search inside themselves to find what sort of “spiritual tikkun” they need to make.

This message may not be much different from what many self-styled self-help gurus offer spiritually hungry audiences. But after years of anonymity as a gay man working for Starbucks, Smith’s adoption of a female identity opened up professional opportunities within a certain niche of the Jewish world: prestigious teaching gigs at the Pardes Institute of Jewish Studies and elsewhere, a motivational podcast, and the publication of a memoir.

In recent years, conversations about transgenderism have played an outsized role in American public discourse, sparking debates over the ethics of giving hormone-altering medications to children, or the fairness of allowing men who identify as women to compete in women’s sports. This is less the case in Israel, where most of the film is set. Although the film makes joking reference to the issue of sex-specific bathrooms, it elides controversial issues and instead focuses on one person’s quest for truth and authenticity—perhaps as a result of the filmmakers’ Israeli perspective.

I Was Not Born a Mistake is, among other things, a documentary about performance. It concerns an individual who painfully tries to perform a series of identities to make up for a void within. Though the film’s narrative arc presents Smith as experimenting with a series of identities we are now meant to regard as inauthentic vis-à-vis the current one, it is not at all obvious which steps in Smith’s journey will last and which are passing phases. The Shabbat dinner guest’s remarks about playacting haunt the film to a degree perhaps unintended by the filmmakers. It is by no means a stretch to imagine that Smith is simply playing at being a woman after playing at being a gay man or a Lubavitch Ḥasid—that this identity is as tenuous as those that preceded it.

One of the roles Smith plays best is that of victim. In a visually appealing segment wherein the newly transgender Smith and a friend visit the Jerusalem synagogue where Smith formerly officiated, Smith gazes through a lattice m’ḥitsah—the traditional barrier between the sexes—into the men’s section with an air of wistfulness, mentioning that it is now off-limits. This moment is perhaps the best expression of the incoherence of the film, or of Smith’s vision. Smith, after all, chose the women’s section.

As for Smith’s theology, on the rare occasions when the film quotes a Jewish thinker, it is to present a watered-down version of such kabbalistic concepts as the shedding of klipot, the impure husks that surround an essential and holy core. The analogy is obvious. But how, we might ask, are we to distinguish between these impure husks and the necessary parts of our physical and spiritual identities that ultimately require a kind of reconciliation? 

In classical Kabbalah, it’s much easier, since the Bible and Talmud delineate what is holy and what is not. A Chabad Ḥasid, similarly, is taught to interrogate constantly whether impulses for change emanate from higher, godly faculties or lower, animal ones. Without any external measure, be it biology, tradition, religion, or anything else, how can we distinguish inner truth from a set of delusions?

The emptiness of Smith’s theology is less troubling than the most urgent question the film raises: What human wreckage is left in the wake of an adult’s quest to discover an elusive self, when that quest overshadows obligations to others? The film implies that while living as a secular gay man and even after adopting the identity of a religious woman, Smith maintained a relationship, however strained, with his children, all of whom remained Hasidic. But when Smith’s children begged for their father’s memoir not to be published, lest it humiliate them, Smith, after vacillating, ignored their concerns. In Smith’s own rather disturbing words, “I am not going to go out of tune so they can be better.” Only two of the six children remain in contact with Smith. Despite this, the audience for the screening at the Jerusalem Film Festival gave the film a standing ovation. I would like to believe that I was not alone in wondering about those children and whether viewers might have been better served to hear some of their voices.

Although Smith comes across sympathetically in I Was Not Born a Mistake, the film’s vision of womanhood as defined by lipstick, colorful formfitting clothing, and standing on the women’s side of the m’ḥitsah is shallow and brittle. Orthodox Judaism seems to appeal to Smith in part because it offers a role to play. A secular woman can dress androgynously in a T-shirt and jeans and do most public things that a man does. In contrast, in order to appear as an Orthodox woman, Smith must wear long skirts or dresses, pray in the women’s section of the synagogue, and perform rituals reserved to women (such as lighting Sabbath candles) rather than those reserved to men (such as putting on t’filin). Motherhood, and motherly devotion to children, are absent. For Smith, it seems, Orthodoxy is a bit like the exaggerated femininity of the drag queen.

One need not claim that God made Smith, or anyone else, a “mistake” to reject the film’s assumptions about gender identity. Life provides myriad opportunities for embracing the “male” and “female” aspects of the personality, if we conceptualize them as just that: attributes, rather than all-encompassing identities. The failure to integrate these attributes is cause not for celebration but for concern. Smith’s story illustrates the rupture of those relationships that demand that we transcend ourselves, and are therefore the most meaningful—such as that between parents and children. That rupture opens up an endless void, which the new-age spirits of self-discovery will never be able to fill.

Sarah Rindner teaches English literature at Lander College in New York.

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