What Happens When a Harvard Rebel Actually Does His Homework

Most people know Shabbos as the Harvard student who sued his university for its spectacular failure to protect Jewish students after October 7. He became a prominent voice in the American conservative movement, testified at high-profile congressional hearings on antisemitism, and emerged as one of the most articulate young defenders of Israel and Jewish identity on the public stage. All of that is true, and all of it matters. But it doesn't quite capture who he is.

What struck me most was the quality of his questions. They weren't the gotcha questions of someone looking for a headline. They were the questions of someone genuinely trying to understand — precise, intellectually honest, and often better framed than the questions journalists twice his age would think to ask.

He wanted to know why Jewish practice looks so different from the Hebrew Bible on the surface. He pressed me on the Talmud, not to score points, but because he'd actually read the attacks online and wanted real answers. He asked about the Messiah, about the meaning of "chosen," about the word goy (which simply means "nation" — Jews are called a goy kadosh, a holy nation, in the Torah itself), and about whether you can be Jewish and follow Jesus. These aren't fringe questions. They're the questions millions of people are asking, often with bad information driving the answers.

What made the conversation rare is that Shabbos didn't pretend to know things he didn't. He'd push back when something didn't add up, but he'd also say, "correct me if I'm wrong." That combination of confidence and intellectual humility is harder to find than it sounds.

At one point he asked me whether I see biblical prophecy being fulfilled in Israel today. It's a question that could easily tip into sentimentality or politics. Instead, it turned into one of the most honest exchanges I've had on camera. My answer was: yes, unmistakably, and also, we're not done. We've been brought back to this land with an enormous unfinished responsibility. The fact that we're back isn't the end of the story. It's the beginning of one we still need to write.

Shabbos gets that. He's the product of two years studying at Aish, and he knows enough to ask the right questions and he cares enough to take the answers seriously.

He closed our conversation by saying I was more interesting and more intelligent than he'd expected. I'm choosing to take that as a compliment.

What I'll say in return is this: in a world full of loud, shallow Jewish advocacy, Shabbos Kestenbaum is doing something harder and more important. He's trying to understand what he's actually standing up for. That, more than any lawsuit or Senate hearing, is what will matter in the long run.

Watch our full conversation below.