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.

Photo 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.”