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The Crease in My Kippah

How a truly terrible Hebrew school student grew up to become an Orthodox rabbi

Hayim Leiter
February 06, 2023
Tablet Magazine
Tablet Magazine
Tablet Magazine
Tablet Magazine

As I sat on my synagogue’s bimah wearing a standard-issue black satin kippah, I felt an awkward sense of relief. After 10 years of Hebrew school, our class had just led Shabbat services to cap off our confirmation.

The rabbi then ascended the pulpit to address the congregation. “Ladies and gentlemen, let me tell you,” he said, “this is by far the worst confirmation class in Adath Jeshuren’s history.”

In the rabbi’s defense, it was probably true. And to make matters worse, it was mostly my fault.

In many ways, I grew up in a classic Conservative family. I went to public school and attended after-school Judaic learning. We had Shabbat dinners and kept kosher—at home. But as I made my way through Hebrew school, I became more and more disenchanted with Judaism. I was a surfer and a skate rat and a bit of a troublemaker.

In those days, board sports were everything to me. If I had been left to my own devices, I would have been riding something all day long. These sports epitomized free expression for me—and Judaism was the exact opposite. Ritual practice felt like a set of rules to a game that I didn’t want to play. It was something only people my parents’ age did, and I couldn’t figure out why. Although I went through the motions of attending Hebrew school, I only did so because my parents required it. When I finally arrived at confirmation, I was so glad to have “done my time” that I didn’t set foot in a synagogue for the next two years.

The Holocaust unit was the only subject in Hebrew school that had caught my attention. I can remember my mother mentioning it every so often the summer before I first encountered the topic in middle school. I wasn’t sure why she did this but it felt like a coming of age—dealing with such sensitive material. As it was for many other American Jews, the Holocaust became the cornerstone of my Jewish identity, and it stayed in my mind even after I stopped going to Hebrew school and synagogue altogether. I was proud of my heritage and I was ready to fight antisemitism in all its forms, even though I never personally encountered it.

In my senior year of high school, two years after my confirmation, I participated in the March of the Living, a two-week program touring concentration camps in Poland and then traveling to Israel. To actually be where so many of our people were systematically slaughtered put many things into perspective for me. The trip not only set my moral compass but also made me question my assumptions about ritual practice.

On the march, I met the person who would become my closest friend. Akiva and I hit it off right away despite religious differences; he was Orthodox and I was a lapsed Conservative Jew, at best. But it made no difference. I like to say that because of our friendship, I became observant and Akiva became a surfer.

Our first stop in Israel was Tiberias, where Akiva asked me to join the minyan for morning prayers. I agreed, even though at the time I wasn’t keen on waking up early for much of anything. We congregated overlooking a breathtaking view of the hills around the Sea of Galilee. It was an awe-inspiring scene. As the participants began to mumble and sway, I waited for someone to announce the page number; it never happened. I imitated the people around me in the hope that no one would recognize my ignorance. I felt ashamed of this lack in myself and was certain that everyone would soon figure me out.

That moment on the hills of Tiberias awakened something in me. Maybe it was the surroundings. Maybe it was because it was my first visit to Israel. Or maybe it was because it was my first time seeing people my age voluntarily participating in Jewish observance. Whatever it was, all I knew then was that I wanted to do what they were doing.

While on Ben Yehuda Street in central Jerusalem, I purchased my first kippah. This shouldn’t have been such a significant event. I had always worn one when eating dinner in my parents’ home and when attending synagogue. But they were always the black satin type with a significant crease down the middle. They lived in the kitchen cabinet above the telephone in our house—and were only worn inside. The one I purchased in Jerusalem was knitted, perfectly flat—and it was mine.

When I stepped out onto Ben Yehuda, wearing it for the first time, I was nervous and jittery. I felt like I was outing myself as a Jew—a peculiar sensation to have while walking the streets of the Jewish state. But my direct exposure to Jewish suffering and observant living taught me how privileged I was to be free to practice my religion. The least I could do was not take it for granted.

When we returned home from the trip, I came off the bus wearing my kippah and dancing the hora with my new group of friends. Needless to say, because of my checkered past, my parents were—to say the least—surprised.

But despite this new connection to Judaism, I feared how people would look at me if I displayed my religiosity in such an overt manner. It was one thing to wear a kippah when surrounded by others doing the same thing; but the world I lived in and the environment I would be moving on to at college were something else. No one in my high school wore a kippah and the University of Rhode Island, where I’d start my undergraduate degree that fall, had no Orthodox presence whatsoever. This thought made me so uneasy that on the ride home from the bus, I folded my kippah into my pocket, creasing it for the first time.

The University of Rhode Island didn’t have much of a Jewish population. The vast majority of the Jewish students were aligned with the fraternity and sorority systems, which I wanted nothing to do with. It took some time, but once I found my footing on campus, I began frequenting the Hillel, along with other student organizations. I spent many Friday nights walking to and from Hillel with my kippah folded in my pocket.

Despite the fact that I wasn’t hiding my Judaism, I still didn’t feel like I could display my religious self for all to see. My identity was split in two: There was my public persona of being involved in many different campus organizations and my Jewish side that came alive at Hillel—when I was indoors.

Throughout college, I wasn’t sure what my career path should be. I tried being everything from a stand-up comedian to a radio disc jockey to a professional surfer, but nothing seemed to fit.

In the hope of getting some guidance, I filled out a computer questionnaire at career services. I answered in the affirmative to such questions as, “Do you like speaking in front of a group?” and “Do you want to be a leader?” The computer’s top suggestion was “clergyperson.”

I couldn’t believe what I was reading—a rabbi? Really? There must have been something wrong with the program. I felt like I knew so little about Jewish ritual and practice that I could not take on such a public role. Still, the idea, much like my experience in Tiberias, continued nagging at me until my senior year.

For the second half of my college career, I volunteered, along with my close friend Mike, to be Rhody the Ram, the University of Rhode Island’s mascot. (We took turns wearing the costume.) The night of Midnight Madness during my senior year was the start of something new. For the first time, the men’s and women’s teams would be practicing together.

In honor of this joint practice, Mike and I organized a skit. As we completed our preparations the night prior, Mike mentioned that he was going out with his friend Fitz on his way to the event. He assured me he would arrive on time.

On their way to Midnight Madness, Fitz took a corner too fast and wrapped the car around a tree. Mike, who walked away with cuts and bruises, didn’t make it to Midnight Madness. Fitz never made it anywhere again.

The following week was a bit of a blur. It was Homecoming, and I was to be crowned Homecoming King at the football game. As it turned out, the game and Fitz’s funeral overlapped. I chose to travel to Massachusetts to pay my respects and be there for Mike.

I never had the chance to get to know Fitz. We were only acquaintances through Mike. But at the funeral, the eulogies made clear to me the depth of what we had lost. In his short time on earth, Fitz had already done missionary work around the world through his Catholic Church. If things had been different, he may have become a clergyperson himself. I was deeply saddened to see someone with such promise cut down way before his prime.

As the memorial was winding to a close, Father John Soares, the head of the URI Catholic Center, rose to speak. “I have a lot of faith in the student body today because the Homecoming King, who’s meant to be crowned right now, is here to pay his respects.” I was overcome with emotion, feeling partially honored that Father John would make this pronouncement—and partially embarrassed that my actions were on display for all to see.

That week taught me more about who I should be and what I should do than at any other point in my life. Fitz taught me that good can be done even in a short amount of time. It still pains me to know that his impact ended so soon.

Father John taught me the importance of being an example for the good you want to see in the world. He showed me that if I genuinely cared about the Jewish people and their future, my impact would be greater if done openly. But beyond that, he helped me understand that Judaism needs to be more than just reactive. It’s not enough to simply defy those who oppose us, I needed to build a positive expression of Jewish living and that meant incorporating Jewish tradition into my daily life. I had to become a rabbi.

I applied to the Jewish Theological Seminary. I had always been a Conservative Jew, so it seemed the logical choice. But my time at JTS was short-lived because I didn’t fit in. I wanted to learn and observe Jewish law in a traditional way and, at the time, JTS resembled a graduate school program. Much to my dismay, I realized that the Conservative movement could no longer provide for my religious needs. I left for the Orthodox world.

The move scared me. Thankfully, my parents have always been open and supportive, from my surfing antics to my religious tendencies. But my move would likely lead them to places they might never have gone otherwise. And I feared my religious observance and the rigidity of Orthodoxy could create tension between us.

Luckily, as my time at JTS was coming to a close, Yeshivat Chovevei Torah, a left-leaning modern Orthodox rabbinical school, was in its infancy. YCT provided me with a safe space to question the larger issues of living a traditional life in the modern world.

Ultimately, my studies led me to the place I now call home: Israel. Here I completed my rabbinic education at Yishevat HaMivtar in Efrat while concurrently learning to be a mohel. It’s as if that first shacharit in Tiberias planted a seed in me of not only the Jew I would become but of where I would one day live.

Akiva and I remained close throughout the years. Our rabbinic learning even overlapped for a year at YCT. A few months ago, he made aliyah with his family and moved to the first floor of my building. It’s hard to explain the feeling of watching our children become friends. We spend many mornings praying together in the Judean hills but we also spend mornings surfing along the Mediterranean coast.

A lot has happened along my Jewish journey. My rabbinical search has been influenced by many other friends and leaders throughout the years. But as crazy as it may sound, I believe I have Fitz and Father John to thank for helping start me on the path. It is because of their inspiration—and Akiva, who originally set me on my way—that there is no longer a crease in my kippah, because I never feel the need to hide it in my pocket anymore.

Hayim Leiter is a rabbi, a wedding officiant, and a mohel who performs britot (ritual circumcisions) and conversions across the world. Based in Efrat, he is the founder of Magen HaBrit, an organization protecting the practice of brit milah and the children who undergo it.