People of the Book

I’ve admired Shabbos Kestenbaum for a while.There are obvious reasons for this. He sued Harvard. He has become one of the most recognizable young Jewish voices in America. He is willing to walk onto stages where neither Jews nor Israel are especially welcome, wearing a yarmulke, and say plainly what he believes.But that isn’t really what I admire most about him.What I admire is his clarity. Shabbos seems to possess something increasingly rare: a willingness to decide what is true before deciding what it will cost him to say it.At one point in our conversation, I asked him where he gets his courage.He resisted the question.He doesn’t experience himself as courageous. When it comes to Israel, the Jewish people, and the 3,000-year-old story he inherited, he doesn’t feel that he is bravely defending some controversial position. He believes these things are true. He feels profoundly fortunate to belong to this story. And standing up for it is, as he puts it, simply “what you do.”I found that answer striking, because it gets at something deeper than courage.Courage suggests overcoming fear. Shabbos was describing something that comes before fear: knowing who you are.That became, for me, the thread running through our conversation.We spoke about his unusual childhood and Jewish upbringing; Harvard and October 8th; Israel; Kiddush Hashem; the story of Yonah; and what Jewish resistance actually looks like. Sometimes resistance means taking Harvard to court. But it can also mean wearing a Magen David. Dating Jewish. Learning Torah. Building a Jewish home. Becoming, quietly and deliberately, a little more Jewish than you were yesterday.And beneath all of it was a question I kept returning to: What happens when a person knows who he is deeply enough that he no longer needs the world’s permission to be it?This is a conversation about courage, although Shabbos might reject the word. It is a conversation about conviction, responsibility, Jewish pride, and the peculiar freedom that comes from knowing that your life belongs to a story that began long before you and, God willing, will continue long after you.

Almost everyone I know who takes their emunah seriously has, at some point, gone through a stretch where the ground felt less solid than they wanted to admit — not necessarily a crisis, just a season of questions that didn't come with tidy answers. I don't think we talk about that enough in our world. We speak about emunah as if it's something you either have or you don't, when for many people it's closer to a current running through a life: it moves, it gets tested, and it comes back different than it left.Rav Norman Lamm once defined emunah as "the continuous tension between itself and the doubt within itself." And the Alter Rebbe points out in Tanya that emunah shares its root with oman — the Hebrew word for artisan, for art. Emunah isn't a fact you accept once and set down. It's something practiced, something honed, something that grows in nuance and richness across the whole journey of a life.Rav Sholom Kesselman directs the OK on the West Coast and serves as a mashpia in the Chabad community here in Los Angeles. I deeply admire him for the clarity of his thinking — the depth and spaciousness he gives to nuanced ideas, and the precision with which he articulates them without ever flattening what makes them nuanced in the first place. That quality runs through this entire conversation. If it resonates with you, you'll find more of his thinking on his substack, Rethink.We don't resolve the tension neatly, because I don't believe it resolves neatly. But I want to say clearly, up front, what I hope this episode says on its own: if you've had questions about your faith, you are not broken, you are not alone, and there is room in Yiddishkeit for you and for your process.I hope you find this conversation as meaningful as I did.

Prof. Benjamin Brown is a Professor in the Department of Jewish Thought at the Hebrew University of Jerusalem and one of the world's leading academic experts on Orthodox Judaism, its ideology, and Halacha. He is the author of many books, among them a towering intellectual biography of the Chazon Ish, and his warmth through a screen and across an ocean was as palpable as his brilliance. We trace the evolution of Daas Torah, the idea that Torah speaks to every facet of life, even beyond the strictly halachic. We explore the revolution of Chassidus and how revolutions mature and stabilize over time. And we arrive at a perspective on change within Yiddishkeit that I found profound: that we evolve precisely in order to remain the same. I found this conversation deeply enjoyable and illuminating, and I hope you do as well.This episode is dedicated in honor of the birthday of my dear Bubby, whose birthday was on Yud Aleph Tammuz. May she have a beautiful and blessed year, full of health and happiness — physically and spiritually — and filled with nachas from her loving family. Bubby, all my love.

Professor Elliot Wolfson is one of the most remarkable minds working in Jewish academic thought today. A scholar, philosopher, poet, and artist, Wolfson holds the Marsha and Jay Glazer Chair in Jewish Studies at the University of California, Santa Barbara, and has spent decades mapping the innermost terrain of Jewish mysticism with a rigor and depth that few can match. Born on the nineteenth of Kislev — the holiday known in Chassidic tradition as the Rosh Hashanah of Chassidus, the day the Alter Rebbe was released from Czarist imprisonment and the inner teachings of the Torah were given new license to flow into the world — one might say his birthday itself portended a life devoted to the depths of Jewish mystical thought. We speak about mysticism and philosophy, paradox, the unspeakable, and what this lifelong quest means to him personally. Thank you for listening!

Rav Shlomo Einhorn is a talmid chacham, a master educator, and one of the most dynamic Rabbis I have encountered. For years he served as dean of Yavneh Academy in Los Angeles before stepping into a world most rabbis haven't touched — artificial intelligence. He is the founder and CEO of Mallacore, an AI consulting firm, and has been thinking and writing seriously about what this technology means for Torah, for learning, and for what it means to be human.What I love about Rav Einhorn is that none of this feels like a contradiction. For him, the move from yeshivah to AI was not a departure — it was a natural development. Because he sees in the architecture of the Talmud something that the builders of AI have been trying to approximate without knowing it.In this conversation we explore his claim that the Talmud is humanity's most sophisticated training manual for artificial intelligence, what AI can and cannot do when it comes to learning Torah, what a yeshiva might look like in 2036, and what will be gained and lost when the next generation learns with tools we can barely imagine today. We also talk about what all of this means for what makes us irreducibly human.This was a genuinely fun conversation. I hope you enjoy it.

Friends, I am so excited to share this next episode of People of the Book — a conversation with someone I truly admire and who has been especially important and transformative in my own life. Rav Schneur Kessler is the Rav of the New Haven community and Rosh Kollel of the Kollel there. He is a talmid chacham par excellence, and one of the rare people whose depth of learning is matched only by his largesse of spirit. We talk about what it means to be a rabbi, how to maintain openness and curiosity amidst the specificity of one's own tradition, how to cultivate interiority in one's Judaism, and so much more. I hope you enjoy.

There are two kinds of holiness in this world: the kind that is given to you, and the kind that you claim for yourself. Shabbos arrives like a gift, and then withdraws when the sun goes down. But the sanctity of Pesach, the added soul that a Yom Tov awakens, is something you reach for from within. Once you claim it, it can never be taken away.Based on a teaching from the Kedushas Levi, and a machlokes between Tosfos and Rashbam about the Neshama Yesaira.