Jason Rubenstein was giving a Rosh Hashanah sermon around the time he graduated from The Rabbinical School of the Jewish Theological Seminary. It started sinking in then that he could possibly consider himself a Jewish educator and leader.  

“There were no do-overs,” Rabbi Rubenstein said. “People weren’t there just for something interesting, but for the real stuff. I was there to help them find it and look it in the eye because it might be too big to see.”

“I can do the most intelligent, interesting, or creative thing. However, unless I’ve done the work of orienting people to the momentous work of being a person and the possibility and tragedy of it, then they didn’t get what they came for. Is that being an educator? I’m not sure. However, that was the first time I felt such weight of responsibility in what I was doing.”

Speak to Rabbi Rubenstein about his trajectory – from his youth in Washington, DC, to Harvard, to JTS, to the Hadar Institute in New York, and now Yale Hillel – and you will hear serious deliberation on moments that remain meaningful to him not only in their singularity, but also in the context of his life’s path and personal and professional evolution.

For example, he cites his participation as a teen in Operation Understanding – a leadership development program bringing together Jewish and African-American youth to confront racism and anti-Semitism – as quite seminal in his early search for Jewish identity and his relationship to Judaism.

“I think about my Jewish life around age 16. It always felt as if there was something beyond the door, but the door was locked,” he said. “Operation Understanding was a key to approaching rituals as serious and real human experiences. They weren’t just a means to focus on justice; instead, they were a way to create moments here and now of redemption, possibility, and reorientation. It was a big thing for me then and it still is now in what I do.”

As a social studies student at Harvard, Rabbi Rubenstein found a home at Hillel under the leadership of 2010 Covenant Award recipient Bernie Steinberg. He described the environment at Hillel as full of “voltage and tension” and “magically deep” immersion in study, learning, and pluralistic community.  While there, he served as Vice President for Education and organizer of the Student Conservative Minyan.

“It was a place where we talked about intellectual things, including Talmud, and people were generous and supportive; spiritual and ethical questions of the day were front and center in macro and micro ways – a holistically integrated experience.”

“I felt that I was not just a member, but a co-creator of a community of meaning. This was Judaism. There were no silos. Judaism was a matrix of different nationalities, ethnic backgrounds, family experiences, and politics, with people being intelligible to each other. This is the life I wanted and wanted to create for others.”

That finding and creating of communities of meaning, informed by an intense and evolving scholarship, is a thread throughout Rabbi Rubenstein’s life – from those searching teenage years through his time at Harvard, as a counselor working with youth through the Nesiya Institute in Jerusalem, and then at Hadar, where he served as Dean of Students and Alumni for eight years.  

Rabbi Rubenstein received the 2015 Covenant Foundation Pomegranate Prize for his promise and potential as a young Jewish educator during his tenure at Hadar. His work there as teacher, spiritual guide, pastoral counselor, and cultivator of participation and ownership positioned him, in his words, to “blossom as an educator.” It helped him find movement between Talmud and text and lives being lived, “using tradition to shed light on life, and life to shed light on tradition.”

“What is so powerful about Jason is the combination of being an incredible scholar, with so much Jewish knowledge, and a gifted relational guide, applying Jewish texts and wisdoms that speak to life issues and journeys with relevancy,” said Rabbi Elie Kaunfer, President and CEO of the Hadar Institute.

Rabbi Rubenstein joined Yale Hillel (officially as the Howard M. Holtzmann Jewish Chaplain at Yale) in the summer of 2018. Reflecting on the move to New Haven in the weeks leading up to the fall semester there, he described an opportunity to create and shape Jewish identities.

“If we do our job right, young people will emerge from their time here with a sense of how fulfilling and exciting and challenging and wonderful it is to be an active and contributing member of a diverse Jewish community.”

“What is always important is mentorship - helping people find their own voices and learn the craft of creating a Jewish life from the resources of Judaism. I have always gravitated toward this. The position at Yale appeals to me because it is not part of the work; instead, it is the work.”

Addressing his selection as a Pomegranate Prize recipient, Rabbi Rubenstein described multiple layers of meaning and honor. He also noted The Covenant Foundation’s convening power, describing it as nothing less than “head shifting” in terms of generated exposures, connections, and ideas.

“It is very clear to me that those who know the Jewish world very well and have an eye for creativity and dedication are excited about letting me do things that might not be institutionally necessary. These aren’t just side projects of mine; they will help me find ways to grow in a more self-directed way and be held accountable for it.”

He used resources attached to the Pomegranate Prize in a variety of ways, from work with a writing coach to complete a book on Jewish thought, growing out of his work at Hadar, to professional coaching to enable a successful transfer to Yale Hillel. He also used some of the resources for singing lessons, which he said “will never get me a job, but will change me for the better in Jewish spaces.”

The notion of being an “emerging” leader in Jewish education, as underscored by the Pomegranate Prize, is one that admittedly intrigues and challenges him.

“There are certain things that I have figured out and ideas that I have tested out enough times and trust. In ten years, I would like to be able to say the same thing. I hope that things that are embryonic now or that are in the background may be in the foreground and will inform my work and impact differently.”