TRANSITION: Former student holds onto religion while changing from female to male

Benjamin Kenner, who attended Shalhevet from 2011 to 2013 as Rochel-Leah Kenner, left in the middle of senior year to begin a gender transition. So far, worshipping on the men’s side of the mechitzah at a Portland Chabad has not been a problem.

January 28, 2016

Imagine waking up every morning and putting on clothes of the opposite sex. Imagine putting on a dress, or a suit and tie, and then going to work or school and being called a name of the wrong gender, and then being referred to with the wrong pronouns. Then imagine realizing you’re just in the wrong body for the gender you know you are. This is how transgender former Shalhevet student Benjamin Kenner explains being transgender. 

“Imagine that, whatever gender you are, everyone insisted you were the other one, and nothing you say seems to convince them otherwise,” Benjamin told The Boiling Point by telephone from Portland, Ore., where he lives now.

“You know deep in your heart that they are wrong, but for some reason they keep insisting that you are the one who is wrong. Imagine living everyday of your life like that.” 

Previously known as Rochel-Leah Kenner, Benjamin left Shalhevet in the middle of senior year to present as male. The girl he used to be came to Shalhevet in 2011 for a second junior year after leaving the Hebrew Academy in Huntington Beach, where she came out as a lesbian in 11th grade in early 2011.

At the time, Rochel-Leah thought wanting to be masculine and wear men’s clothing meant she was lesbian. As a lesbian, she didn’t personally experience any bullying, discrimination or animosity at Shalhevet from 2011 to 2013.

“It took me a while to feel brave enough to come out, but once I did people were pretty cool about it,” he said. “They were still as homophobic as they were in general, but none of it was ever directed at me.”

However, when the subject of changing genders came up, she felt different vibe.  One day, a video about transgender people was played in Ms. Tove Sunshine’s AP Psychology class. 

“I have a vivid memory of smiling at my desk, and the kid next to me recoiling in horror in his seat,” Benjamin said.  

Today, Benjamin works at a home for adults with developmental disabilities, a “dream job,” he said. After leaving Shalhevet, he eventually got a high school equivalency diploma (GED). 

At Shalhevet, then-Rochel-Leah was active in drama, Litmag and poetry readings, and was also one of the first girls to volunteer to carry the Torah through the women’s section during Shacharit.

Being part of both the Modern Orthodox and LGBT communities began to seem contradictory – and still does, he says, because he still believes in God. 

“Sometimes I was very angry at God, but I always believed in Him,” Benjamin says. 

He knows he would fit in better at a Reform or Conservative synagogue, but when he tried a few Conservative synagogues in Los Angeles, he always felt uncomfortable. Ultimately, he wants to find an Orthodox community similar to B’nai David-Judea, which he attended during high school.

When she arrived at Shalhevet as a lesbian in 2011, Rochel-Leah Kenner was already having much stronger inklings of being trans, something she had ignored since the age of 11, when she told her mother if there were gender-neutral pronouns she would use them. She also began wearing pants, something she had put off for years following her family’s religious practice.

Finally, in the first semester of senior year she could no longer ignore her transgender feelings. She came out to many close friends, including David Lorell ‘15 and Talya Joffe ‘14, who were all very accepting. 

“He — then she — told me, very emotionally, about the horrible struggle that he was having with being forced to adopt the practices of being female at school — wearing skirts, worshipping in the female fashion, etcetera,” David Lorell said. “It was really moving. I can understand why he felt the need to leave.”

Still, Benjamin decided not to come out as transgender to the wider community of Shalhevet, assuming it would amount to nothing.

Benjamin cutout copyPhoto Courtesy: Benjamin Kenner

“I thought, I’m still going to have to present as a girl at school, so what’s the point?” he said.

During winter break of 2013, Benjamin Kenner sent an email to some faculty and the administration, which then consisted of Head of School Rabbi Ari Segal and General Studies principal Roy Danovitch. He explained he would not return to school for the second semester. 

“I felt many conflicting emotions,” Rabbi Segal said in a recent e-mail interview about it with the Boiling Point. “For one, I was sad – sad that Benjamin felt that he had to leave Shalhevet and that we would not see him around school anymore.

“But I also felt really happy – happy that Benjamin was able to take that kind of step and begin the process of being truer to himself.  Ultimately, that’s what we want.”

Rose Bern ’13 remembered when she found out about Benjamin leaving.  The transgender part was not what stood out.

“I’ll never forget it–we were sitting in advisory with Mr. Buckley and he explained that the administration had recently received an email from Benjamin saying that he was leaving school, fled to Portland, Oregon, and ended the email by saying that his new name was Benjamin,” said Rose. “And my best friend, Brianna, and I were astounded – this individual who we saw every single day and acted with in plays was gone.”

In Portland, Benjamin has been working toward transitioning. After getting a letter of approval from his therapist four months ago, he began receiving testosterone injections. He is now a part of Chabad at Portland Campuses, a Chabad house near Reed College, where it is known that he is transgender. 

“The vibe I get is that they don’t want to put up a fight,” said Benjamin. “They let me stand on the men’s side, but they don’t count me in a minyan, they don’t include me in a lot of male things, they didn’t let me wear tefillin a while back. It’s clearly very uncomfortable for them.”

The Boiling Point contacted the Benjamin’s rabbi there, Rabbi Dov Bialo, who declined to be interviewed. In an e-mail he wrote, “Thank for reaching out to me, but I would like to shy away from this interview.” 

Benjamin plans on purchasing a pair of tefillin when he has the money to do so. He added he would like to eventually read from the Torah and lead a minyan, something he has wanted to do for years.

Benjamin’s parents are an Orthodox father and a liberal mother who converted in to Judaism before he was born. Benjamin says his mother has always been very supportive of him, and his father accepted him as a lesbian about a year after he came out.

“He still does not accept me as transgender, he refuses to talk about it,” Benjamin said. The Boiling Point tried to reach Benjamin’s parents but was unsuccessful.

He said his father does not believe transgender people exist.

While the rabbis of the Talmud recognized the existence of individuals who didn’t fit a strict gender categories, religious law on the subject is not clear. (See related story, below.) 

Benjamin is not the first Jew to stay religious after going through transition. Another is Rabbi Elliot Kukla, who currently works for the Bay Area Jewish Healing Center in San Francisco, became Reform. 

“A lot of people see me as a gray area, even though I don’t feel like a gray area,” said Rabbi Kukla in an interview with the Boiling Point.  “Still, in halacha, there’s an acknowledgment of those who don’t fit well in the binary … there’s acknowledgment we exist.”

Rabbi Kukla was ordained at the (Reform) Hebrew Union College – Jewish Institute of Religion (HUC-JIR) in Los Angeles.  Reform synagogues count both men and women in minyans, so there is no issue of his gender there.

Then there is Yonadav Kenyon, an Orthodox transgender man in Illinois who transitioned twice. Born male, Yonadav transitioned to be a woman in his mid-20s and lived as a female for 17 years before becoming ba’al teshuva, religiously observant, and transitioning back.

In an interview with the Boiling Point, Yonadav said he felt he could not become religious – as he put it, return to teshuva, or repentance — without returning to his gender at birth, the one he feels God intended him to be. 

But he does not regret his earlier transition and sexual reassignment surgery.

“I always say had it not been surgery, I would be dead right now,” Mr. Kenyon said. “The kind of person who needs to get the surgery starts engaging in self-destructive behavior, because they have anatomy their brain will just not accept.”

Mr. Kenyon says that his sense of yirat shamayim — fear of Heaven — was greater than the pain of reacquainting with his male self, which he said was ironically made easier by the surgery. 


Any remorse he has about his initial transition, he added, comes from its limiting of his marriage prospects, the possibility of raising children, and confusion he gets from people who learn of his past. 

Jenny Newman ‘11, a Shalhevet alumna who is lesbian, believes the passage for Orthodox transgender Jewish people will be upstream because gender roles are so clearly defined in Jewish law and practice. 

“You don’t really fit in any prescribed boxes, which makes it understandable that the Orthodox community has issues,” said Jenny. “I understand why, but it doesn’t bother me any less.”

Jenny said that while she was at Shalhevet, classes and sex ed assemblies never addressed what it meant to be gay, lesbian or transsexual. 

This year’s upperclassmen said it hasn’t come up during their time either.

“It is extremely problematic because it drives away young Jews away from Orthodoxy,” Jenny said.  

Benjamin Kenner agrees, and hopes that the peace he is finding personally in his new gender can one day be a characteristic of Orthodox Judaism in general.

“Orthodox Judaism has as many queer people as any other group, even if we don’t want to admit it, and they’re struggling,” Benjamin said.

“Our queer members are feeling like they have to hide, and that’s really hard when you want to be a part of a community.” 

For transgender, halacha ventures into unknown — or does it?

By Hannah Jannol, Staff Writer

Modern Orthodoxy has been considering the topic of gay and lesbian Jews for a while, but transgender Jews present a challenge which is just beginning to be explored. 

There’s no set dogma on the topic of modern day transsexual people, because the phenomenon postdates second- and third-century Talmud.

“Halacha doesn’t have a prescribed category for these issues,” said Judaic Studies teacher Rabbi Ari Schwarzberg. “So the issue is how do we apply other halacha categories.” 

Most rabbis are not well-acquainted with the issue, and have likely not met a transgender individual. Even those who could rule on the topic of transsexualism are limited to the worldview of their particular yeshiva or university or community, said Rabbi Schwarzberg.

Similarly, a lot of the technology, techniques and medicine used in modern day gender transition didn’t exist even five or 20 years ago, which makes it increasingly difficult for rabbis to pasken, or halachically decide, what to do when transgender individuals are in their communities, Schwarzberg said. 

However, there are commandments that might discourage a halachically observant person from transitioning to a new gender. In cases of male-to-female transitions, castration, or sirus, is prohibited in Leviticus 22:24. For female-to-male transitions, this is only a rabbinic prohibition. 

Based on Deuteronomy 22:5, a natal man or woman wearing the clothing of the opposite sex is also against the law, and “an abhorrence unto Hashem.” 

Male-to-female sex changes may also be prohibited by Leviticus 18:22, the verse famously interpreted as forbidding homosexuality. A commentary by Ibn Ezra quotes Rabbeinu Chananelben Chushiel, an 11th-century rabbi from Tunisia. “There is one who took on the anatomy of a woman, which is not naturally possible,” Rabbeinu Chananel writes. Therefore, he said, this person is now not a woman, but “an androgynous.”

Judaic Studies teacher Morah Atara Segal says this does not necessarily extend to female-to-male sex changes.  It’s possible Rabbeinu Chananel was speaking about men transitioning, she said, because biblical Torah speaks about humans as men as the default – but it’s also possible he was specifically talking about people born as males. 

“It’s also important to note that this is not a Torah prohibition – it’s a biblical commentary that is interpreting a verse in the Torah,” Morah Segal said. 

On the other side is the principle in Jewish law of pikuach nefesh — literally “saving the soul” — which states that saving human life is more important than following any halacha except for laws against murder, adultery and idolatry. Some say that would justify gender changes because for most transgender people, transitioning is a matter of life or death. Prior to transitioning, and at the height of feelings of being in the wrong body, many trans individuals become suicidal.

 “The risk of someone seeing Jewish law in such a way that could potentially cause even one person to damage themselves, hurt themselves, kill themselves, that becomes something Jewish law takes the most seriously,” Rabbi Schwarzberg said.

“The Gemara says you should live by the mitzvot, but you should not die by them,” he continued. “That’s the way we understand the Torah — the value of life, of pikuach nefesh, is paramount.”

Rabbi Yona Reiss, who is currently the Av Beth Din of the Chicago Rabbinical Council and from 1998 to 2008 was the Director of the Beth Din of America, agreed with Rabbi Schwarzberg, while noting that pikuach nefesh is not a consideration that would create permanent law.

In a telephone interview with the Boiling Point, Rabbi Reiss said that even though pikuach nefesh is not enough to change the law, which is immutable, it can be applied where it is relevant to a certain individual – just as it is permissible for an individual to eat non-kosher meat to save his life, but that doesn’t change the law to permit non-kosher meat to all. 

“The goal is to safeguard halacha while at the same time helping people, regardless of their challenges, to live positive and fulfilling lives within that halachic framework,” Rabbi Reiss told The Boiling Point.

The suicide statistics involving transgender people, Jewish or not, are staggering. According to the National Transgender Discrimination Survey (NTDS), 41 percent of transgender individuals attempt suicide at some point in their lifetime, compared to 4.6 percent of the overall population of the U.S. (The same figure among lesbian, gay and bisexual adults is 10 to 20 percent.) 

Benjamin Kenner, who attended Shalhevet from 2011 to 2013 when he was still female, was not immune.

 “I was talking to a friend of mine and said ‘I want to die, I can’t do this — I want to transition and I can’t,’”  Benjamin said he told a Shalhevet friend early in 12th grade. At the time, then-Rochel-Leah Kenner felt trapped out of both her community and her religion, he said.

What turned the switch, he recalled, was when the friend replied: “I think God would prefer you trans and alive than dead.”   

 “If God cares about me, then God wants me to be alive and okay,” Benjamin said last month.

Benjamin says his mental health has never been as good as it was the week of his first shot of testosterone, and every week he keeps getting better, making him a literal example of pikuach nefesh.

But Benjamin doesn’t believe Judaism should wait for a transgender person to become suicidal — to enter that territory of risking their life — before being allowed to transition. 

“We need to not think of transition as the last option,” Benjamin said. “We need to actually love and accept our trans community members and listen to what they say they need.” 

 Once transgender Jews fully transition, even more halachic questions come up. Can a trans man wear tefillin and read from the Torah? What side of the mechitza do transgender Jews stand on? Are transgender men counted in a minyan? Are transgender women, even if they are on the women’s side of the mechitza, exempt from time-bound commandments?

Rabbi Reiss said this all depends on whether or not a transitions “works.” 

In an email to the Boiling Point, he referenced an article by Rabbi David Bleich in Contemporary Halakhic Problems, saying that the normative halachic view says that a sex change operation would be halachically ineffective in changing a person’s gender. 

“Rather, a person would be halachically considered as remaining the same gender as they were originally born,” Rabbi Reiss said. 

But there is evidence for exceptions even to this. Rabbi Reiss brought up a case decided by Rabbi Asher Weiss, a Haredi posek in Borough Park, Brooklyn, of two Jewish people who were getting a divorce. The husband’s father, Daniel, had transitioned to become a woman. For the purpose of finalizing the get, or religious divorce, he decided, the scribe should not write “son of Daniel,” but use the father’s new name and say “son of Ronit,” because Daniel is no longer in use.

Rabbi Reiss also quoted the Tzitz Eliezer – Rabbi Eliezer Waldenberg, a halachic medical ethicist who died in Israel in 2006.

“Even the Tzitz Eliezer, who articulated the minority opinion that a sex change operation can alter a person’s gender from a halachic perspective, only addressed the issue of whether the wife of a man who became a woman would require a get,” Rabbi Reiss said in an email to the Boiling Point. 

“Any extrapolation of his opinion with respect to other halachic ramifications, such as obligations in mitzvot,  ‎is speculative in nature since he did not explicitly address those issues.”‎

All this illustrates Rabbi Schwarzberg’s point that rabbis have few cases and minimal real life experience to base decisions on, and the law is still evolving.

“Your average rabbi who might be a great scholar and might be very knowledgeable might not have a lot to offer on this topic because of lack of experience,” Rabbi Schwarzberg said. “They were certainly never educated on it, and the issue probably hasn’t come to their office, to their shul, to their community yet.”

What if a transgender student came to Shalhevet, or if a student who was already here decided to transition in one direction or another while attending the school? 

Rabbi Segal says he would consult with the poskim. 

“If a student at Shalhevet came out as transgender, regardless of their original sex, which I think is irrelevant to the question, I would consult with my halachic mentors in order to address particular policy issues,” Rabbi Segal wrote in an e-mail. “As an Orthodox school, that’s always an integral part of any plan of action.”

Although obeying halacha is important to Rabbi Segal, inclusion of transgender individuals within that halachic framework is significant as well.  

“It’s our job to consult with our poskim and to maximize our inclusion of all people within a halachic framework, when it comes to policy decisions that affect the school,” Rabbi Segal wrote. 

While even the most authoritative poskim, such as Rabbi Reiss, do not have a clear answer to many questions about what might be called “transgender halacha,” Rabbi Reiss says the answers needed will be found, situation by situation.

There is a rich halachic literature, he said, capable of eventually addressing whatever comes up.  

“There is the human element in every single case, it’s very difficult to look at it solely from a clinical and technical perspective,” Rabbi Reiss said in a phone interview last month. 

“In every individual case one has to address the individual questions, and be very sensitive toward the situation regardless of what the halachic answer is going to be. Ultimately, of course, we have to follow the halacha.” 

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  • Y

    Yonadav KenyonMar 13, 2016 at 5:39 pm

    I would like to clarify a few things, here. I feel a bit misrepresented in this article. I would not have agreed to be interviewed for this article, were it not for the fact that I felt that it was important to impress a very important point on the writer. The greatest cause of stress on transgendered people, is people who won’t mind their own business. Whatever one’s opinion is on gender identity disorders, it doesn’t change the fact that the transgendered have a right to basic dignity and privacy. After all, when I see someone eating a bacon cheeseburger or driving on Shabbat, I don’t go around telling everyone. Likewise, if I know that someone is transgendered, I keep it to myself. I treat them in accordance with the gender that they self-present as.

    I agreed to be interviewed after a person outed me to the writer without my permission. I was outraged by this, and really intended for the point about respecting the privacy and dignity of people who suffer from gender identity disorder to be my primary point in the interview. All that made it into this article, were the few words that could be used for a particular polemic spin.

    I realize that the writer is a teenager. But I think that her teachers should be teaching her journalism, and not polemics.

  • H

    Hanna TürFeb 7, 2016 at 4:16 pm

    Terrific story by a very promising writer.