In a polarized age, how do we raise young Jews who can think deeply—and listen across disagreement?

In this episode of Identity/Crisis, Yehuda Kurtzer talks with principal of SAR High School Jonathan Kroll about his recent commencement address to SAR’s graduating class of 2026, where he challenged students to embrace a “revolution of moderation,” and integrate conviction with openness. Together, they explore pluralism in Orthodox education, the formation of Jewish identity, and what it means to prepare the next generation for a divided world—without sacrificing commitment or clarity. 

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Strong Beliefs and Open Minds: A Graduation Challenge Transcript

Note: This is a lightly edited transcript of a conversation, please excuse any errors.

Yehuda: Hi, everyone. Welcome to Identity/Crisis, a show from the Shalom Hartman Institute, creating better conversations about the essential issues facing Jewish life. I’m Yehuda Kurtzer. We’re recording on Thursday, June 11th, 2026. 

My son graduated this week from high school. It was a wonderful and predictably emotional experience, both for me and visibly at graduation, for him. I’ve come to appreciate what seem like evolutionary anthropological behaviors in my children as they grow up, as they start to literally enact with their bodies the separation they’re making from family and into a newly defined self, the ways they start testing boundaries and bedtimes, changing the way they communicate with us. They do so much habituating to leaving that the ritual, like graduation, is better understood as a marker of new realities that have already kicked in than they are like turning points that are just starting to emerge. 

As my kids get older, I move from being more amused by them to just being in awe of them, although I’m still amused by them, don’t get me wrong. And when I get to witness their milestone moments, how other adults and their peers see them, to get to watch their life transitions, it’s intense and it’s awe-inspiring. Anyway, that was my mindset on Monday night, in addition to managing family, in from out of town, planning a dinner outing, finding decent seats in a crowded and frenzied venue with no assigned seating. I have some commentary about that. That was my mindset. I expected some of the whooping and the tears that would follow, the delight and the cringe that comes with the student speakers, and I was looking forward to some big hugs. 

But I didn’t anticipate being so thoroughly moved by the speech of the principal of the high school, Rabbi Jonathan Kroll, who’s joining me today as my guest. Rabbi Kroll, who shares leadership of the high school with Rabbi Tully Harcsztark, which is something maybe we’ll talk about, quoted from, I believe, his childhood friend, Jon Polin?

Jonathan: Yeah.

Yehuda: Who had come to speak at SAR this year with his wife, Rachel Goldberg Polin, and at one point in his talk made the case for a revolution of moderation. Jon Kroll then dug deep into this idea. He argued that Jewish tradition gave us one model to think about moderation, Maimonides’ famous golden mean to walk the narrow line between the extremes. 

But Kroll rejected this model. He said it took away the passions of the extremes, and instead, he cited approvingly the model advanced by Rav Kook in the 20th century of the unification of the opposite views, a way of thinking of identity and community as requiring our willingness to integrate into how we think and how we behave multiple, even competing, viewpoints and people.

This is an approach that generates humility against certainty. It fosters peoplehood over polarization. It invites the passions to guide our lives, but tries to put in place guardrails against their overreaches. And he challenged the students to think about this as the antidote to the algorithms, the divisiveness, the tribalism, the narrow thinking that plagues our society.

I was mesmerized by the speech, as was Stephanie next to me. I wondered at times whether the graduates, amped up by the whole experience of dancing into graduation, all of the excitement, all of their nerves, whether they were able to hear it then. I really hope that they did and I’m sure a lot of it got in, in the same way that much of our teens seem to learn is by some amount of passive absorption and osmosis.

It wasn’t so much that I loved it because I agreed with it. I mean, a passionate and learned pitch for pluralism? Yes, please. No, I loved it because I also felt there was something risky, even prickly, about the speech. See, when you speak to Jews who identify first and foremost as liberals, who are not necessarily good at pluralism, but ostensibly believe in it, well, that’s preaching to the choir.

But SAR is an Orthodox school connected to multiple different Orthodox communities. Orthodoxy, befitting its name, makes strong truth claims that are hard to juxtapose and to live together with counterclaims. Orthodoxy is rooted culturally and behaviorally in a measure of separateness from others. And while Rav Kook was an Orthodox rabbi, he was also an early, dangerous 20th century Palestine, where the matter of creating some alignment between secular pioneers and the small and fragile Orthodox community was a matter of existential necessity.

But today, in Riverdale, where I live, in White Plains, New Rochelle, Teaneck, Englewood, some of the core communities that shape the SAR world, you can live a life of modest but necessary integration with the non-Jewish or the non-Orthodox world, maybe at your place of business. But it’s also truly possible to live a life that is predominantly set apart from others. So to challenge a community like this to think differently about its responsibility to listen to and integrate competing ideas was courageous and provocative. 

So now it’s the end of the school year. I’m so happy for everyone involved in that. I can see it on my friends’ faces who are school teachers as they encounter the break of dawn of summer vacation on their horizon. You see it in all the children slogging out these final weeks, desperate to be released, as the Midrash lamentingly describes the Israelites as they fled Mount Sinai like children fleeing from the schoolhouse. 

It’s as good a time as ever to pause and consider the question of what we are doing when we teach children, when we challenge them, when we challenge their parents, and when we have to distill our final messages for them when they’re about to encounter the world, ready or not.

So I’m delighted that Rabbi Kroll, Jon, if I may, agreed to be on the show today to talk about his ideas and leadership. It’s good timing that, like, school’s basically over, so actually he was available during the day. And I also just want to say at the outset, this is not the first Ives-Kurtzer-Kroll podcast collaboration. My son Jesse and Rabbi Kroll did a podcast together for the school over the course of this year. It’s a good listen. 

I’ll start just by saying this is a good time as ever to say thank you to you, Jon, to the school, and to the teachers for all that you gave to my son for the last four years. So thanks for being on the show today.

Jonathan: Thank you so much. I really appreciate that. And also, thank you for that plug for the Being podcast of mine and Jesse’s. That was really generous of you. 

I’ll tell you something interesting. I was not expecting to get as much positive feedback or interest following my speech the other night at graduation. I spent a lot of time thinking about it. And that’s something I’ve been thinking about for a few months actually, and I worked hard crafting the language, and revising, and thinking how I wanna organize my thoughts. Usually one person will say like, “Nice speech.” I had much more than that.

Yehuda: Wow.

Jonathan: A lot of grandparents who were in the audience. I got emails from them asking for a copy of my speech. I was very moved by it. I wasn’t expecting that, and I guess it must have hit a chord in certain ways. 

Now, I think what’s also really interesting, you framed it as very aligned with what’s, we’ll call it a more pluralistic community. I was getting a lot of feedback positively, both from people I would consider to be arch-conservative, you know, not liberal, not pluralistic in general. But people who like wanna engage the world of ideas. Almost like more like, I think Bret Stephens has written a lot about, like, the University of Chicago anti-cancel culture. I was getting equal measure of positive feedback from people who I would identify more along a conservative line of thinking as those who were amongst a more liberal line of thinking, because people want to be able to think seriously, to be challenged, to be confident in their beliefs it feels like.

And also, there is a sense of like people just gotta calm down a little bit, and relax, and like just be normal. People can engage in conversations without feeling like, that the stakes are so high, but just to actually engage and think. 

Yehuda: Yeah. There’s a lot of interesting observations there, and a lot to say about the ways that liberals hear this story, and the way that conservatives hear this story, and still the way they paint the other as being part of the problem.

And it’s like an interesting thing, like there’s probably a much larger coalition than is available to us in our partisan world of people who basically believe the same thing, but have different rhetoric about who’s causing the problem or what it’s supposed to look like. So we could talk about that.

What I wanted to start with is when you are crafting a message like that, I wanna talk generally about what you’re hoping to do at a graduation, right? But I also am wondering specifically about this speech, what you were seeing in your students that led you to say, “This is the message I have to give to them.” It can’t just be like when you encounter this stuff outside of the world. You’re obviously seeing things in them that this is your big opportunity, and your last bite of the apple to tell them, you know, a piece of mussar or a piece of guidance. 

Jonathan: Yeah. That’s a great question. You asked two questions—

Yehuda: I did.

Jonathan: So I’ll answer them both. I’ll say when I’m thinking about the message I’d like to deliver, I’m thinking about a message that people will feel resonates, something that the students will say, “Yeah, that’s right. I didn’t think of it that way before, but yeah, thank you for putting into words something that was sort of a theme that may have been present in my education or something that’s happening in the world right now that I can’t really articulate clearly, but yeah, that’s it.” That’s what I want my kids to say. 

I wanna do so in a way that feels like it’s a message that resonates with what I see as the school’s mission, so that the young adults, as they graduate will, like, sort of get a final message from the school, which is something that resonates with school values. 

I also think about the parents who are in the audience as well. I’m thinking that I want the parents to understand something about what I see as the school’s values, and what I also see as something that feels important. In other words, I’m not only trying to see a speech at graduation as a nice review and a PR speech for the school. I’ve tried, over the past years, to think of a message that I think people would feel is resonant with the times, and something that feels important.

To the extent to which that works, I’m happy, but I don’t assume that it necessarily will land, but I did feel like it landed pretty well with a lot of people I heard from. That’s in terms of, like, what I’m thinking about in crafting. 

Yehuda: What is it about these students that you see in them that demanded this kind of message at this time?

Jonathan: Okay, so this is gonna sound funny, because we are, on a certain measure, for an outsider, our school is an extremely homogeneous environment. You know, we’ll call it sort of Modern Orthodox, suburban, upper middle class demographic, which to an outsider it’s like everybody’s exactly the same. 

If you live inside the building and inside our school—I think it’s probably this way with many institutions—the diversity feels like it is overwhelmingly enormous. Diversity of family backgrounds, of political views, of religious attitudes, and that kind of thing will show up in, like, very simple things, when you have mock elections for a presidential election. You know, just like in America writ large, there is a divide, which I think is a little bit different in our school. It reflects a little bit more of that divide, I think, than you have in some other Orthodox yeshiva high schools. It is a little more wide-ranging. And so that is something that I think our students have encountered as a challenge that they’ve liked. 

In other words, this was coming as much from my thinking about being open to many ideas, even those you don’t agree with, but to certainly listen and allow yourself to be challenged even if you’re not going to accept another opinion, as much by, like, my thinking almost, like, philosophically, as it was by trying to put words to what I think our student experience was over the past number of years, which is, you can have a kid who might be a Trump MAGA guy with the red Make America Great hat, Again, and somebody who was a supporter of Mamdani running for mayor in New York. Those two kids could be in the same class, and they may totally disagree with each other. I’m painting two extreme pictures. Most of them are in the middle between those two. 

Yehuda: Sure.

Jonathan: Those two kids could be in class with each other and really vigorously disagree with each other, but to do so when talking about ideas and not ad hominem, and to feel that they’re better for it. In other words, this was considered to be not a flaw, but a feature of their education. 

Kids, when you put them in the position of an environment that fosters respectful debate, civil discourse, they may at first, your initial reaction if you’re a kid is to, like, you know, wanna deny a validity of somebody else’s argument, to almost, like, deny their space to make that argument. But eventually our experience has been that the kids value it, and they feel that they’re smarter for it, and they feel that they’re nicer for it, and that they want to reject that algorithmic echo chamber that they’re getting on their social media feeds which just feeds the rage. And there’s something about school feeling a little bit of an oasis or a refuge from that world that feels like it’s just so angry and unpleasant.

Yehuda: In other words, you were saying to your students, like, this was a feature of your experience. You will enter into many environments of your own choice where you could actually avoid this, like opt back in to the kind of environment we’re creating. 

Jonathan: Yeah. Yeah, the opt back in, I’d say, is to create those spaces to make sure that if you liked this, keep it going and don’t assume that that’s something that was gonna naturally happen. You can do real things that would foster that environment. 

Yehuda: It reminds me actually of something that Dr. Rivka Press Schwartz, administrator, colleague of yours at the school, and was a Hartman fellow for a number of years with us. She said this a few years ago that, certainly in the Jewish community and maybe even beyond, Orthodox day schools, especially like SAR, are among the last remaining bipartisan spaces in the Jewish community, that they are still laboratories, because, you choose an Orthodox day school because it’s in your area and it connects to the larger Jewish values you want to educate towards, and some parents I’m sure are like, “I don’t want to send my kid to that school. It’s too liberal.” “I don’t want to send my kid to that school. It’s too conservative,” on the American political side. But it’s oftentimes a much more alchemy of considerations of why people go there and what the opportunity that then creates for the educational system. 

Jonathan: Yeah, I think that that’s right. I’ll also point out, as you said in your introduction, this is an Orthodox school and there are positions, beliefs, philosophies that we believe to be true and we want our kids to engage, and we’d love our kids to adopt and value the school’s values. In other words, I want to be very clear. It’s not like, you know, it’s not—

Yehuda: Yeah, I want to dig on that.

Jonathan: It’s not, it’s not like an “anything goes.” For example, let’s say in terms of, you know, Jewish practice. So the school’s position is that you’re supposed to be halachically committed, following halacha in all regards in life. 

Now, I also think, though, it would be critical for students to be able to have exposure to ideas that don’t fully agree with what we’re saying, and to, like, allow that exposure to happen in a real way, both for the sake of, like, seeing whether there are aspects of a philosophy that you may reject as your own philosophy, other aspects of it that you actually can learn from. That’s more the Rav Kook piece, I think, of the achdut ha-avachim, the unity of opposites. 

There is truth in many different places, even if you are in a position where I accept this sort of truth and this is the community that I’m living in and I want to promote the modern Orthodox philosophical approach and the way of life.

At the same time, as I mentioned when I was speaking, I can take a look at, I want to understand, let’s say to my right, a Charedi position. I’d like to take it seriously, even if I reject it. I’d like to understand where they might be coming from, see whether there’s aspects of it that I think maybe I can learn from and see certain truths in it.

And similarly, I would like to see other denominational beliefs. What do Conservative Jews believe in? What do Reform Jews believe in? What do Reconstruction—What do they believe in? 

It’s not, “Here’s a palette of ideas. Please choose a la carte what you’d like to believe, because anything goes.” I’m not saying that. I’m saying, this is what we believe in. I also want you to understand your own beliefs, and you’ll understand them a heck of a lot better if you understand what they are not accepting, and you can contrast your beliefs with others’. So again, there is an element there that has pieces of pluralism in it, but it’s also a little more circumscribed than that.

I’m happy to, to dig further in that, which I think—

Yehuda: Yeah, let’s dig into that a little bit more because it’s a very tricky piece of business. Because the bad way of doing it is basically like Hasbara, which is, I’m gonna explain these other positions in such a way that it is gonna kind of predetermine that this is the best outcome, or it’s even phrased in Jewish tradition like, “da’ama la’hashiv la’apikoros.” You should know what to respond to a non-believer or a heretic, so that means you have to kind of understand their arguments, but you have to come back with a counterargument, which is very different from the genuine open encounter to different possibilities and beliefs about the revelation on Mount Sinai, the authorship of the Torah.

And the school does have its thumb on the scale, and this is not a criticism. It’s like—

Jonathan: Yeah.

Yehuda: It’s what you pay for.

Jonathan: Right.

Yehuda: Of a worldview and a viewpoint. So you’re not gonna go with this, but I wonder whether it’s just more possible at a school like this for that to happen in the secular studies classrooms, in an English literature classroom, than it might be in a Talmud or a Bible classroom. Because the weight of getting it right or getting people to the right conclusion is much more severe when it comes to the kind of Jewish commitments of the school. 

Jonathan: I think it’s an interesting question. I would say, yeah, you’re right. Our thumb is on the scale. The boundaries are looser when it comes to certain things like political discussions, although I would say that I’m not entirely sure that’s true. I say this all the time, in our community, sometimes I do get frustrated and feel that certain orthodoxies about political beliefs seem to be more orthodox than religious practice. 

Yehuda: Than religious beliefs, yeah. 

Jonathan: Religious belief. I, I think that that frankly is new. When I say new, certainly not when I started in education 30 years ago. It didn’t exist. And it’s not just ’cause I was a younger educator. Nobody knew who was conservative, who was liberal, who voted Democrat, who voted Republican. Those were interesting parts of a person’s personality, but they weren’t identifiers of who they are. That is different nowadays, and that—And so I’m, I’m—

Yehuda:  And it’s not just you. That’s borne out by all of the research on this, yeah. So go ahead, sorry. 

Jonathan: Yeah, and it’s not so clear to me that having that openness in the general studies classes is easier to pull off than doing it in Judaic studies classes. But you’re right in saying Jewish studies classes, there are boundaries that we’re not gonna cross.

As a grown-up adult who has read a lot and, like, learned a decent amount, I’m familiar with, like, you know, let’s say approaches towards authorship of the Torah, that I’m not sharing developmentally with students in high school to look at it as here’s one approach is to say that Torah is Mi-Sinai, Torah Min Hashmaim, and there’s another approach that would say that it is multiple authors over a period of time. We’re not teaching those as viable options in the same way we would be teaching, let’s say, in the history class, what this is, what’s happening right now in the matter of a debate about immigration policy or something like that. 

But I do think as opposed to teaching something as, here are a few options of things you might want to think about, there’s somewhere in between your characterization of, like, here’s a pluralistic palette of ideas, versus you should da’ama la’hashiv, know what to say to the heretics. There’s something in between those two, which is to say, “Here’s what we believe in. Here’s why we believe what we believe in. There’s also value in understanding what other people believe in, even if you don’t believe in it.”

Ultimately, people are gonna make decisions about what they believe in. I don’t control people’s minds, but I do want to convey to them what the school’s philosophy is, what we think is right. It’s different than da’ama la’hashiv. There is a value in being able to respond to critics. I understand that. But I also think there’s a value in, I mentioned it in, when I was speaking the other day at the graduation, I think I used language that I probably had taken from Daniel Taub’s book. 

Yehuda: Yeah.

Jonathan: Actually, Jon Polin had mentioned that when he spoke at SAR on Yom HaZikaron, so I went out and bought that book. It was a great book. 

Yehuda: Yeah, it’s a nice book. We had him on, too.

Jonathan: Yeah. Beyond Dispute. I appreciated a lot of what he had to say in that book. One of the things he mentioned there, he quoted somebody talking about creating, not straw men when you engage in conversation of, of people you disagree with, but creating steel men. Maybe you’ll be convinced of some truths in it, but at the worst-case scenario, you’ll better understand what you believe in because you’ll see what the other approach is. 

So I get, do you understand what I’m saying? That there’s somewhere in between?

Yehuda: Yeah.

Jonathan: Total openness and da’ama la’hashiv which is let’s understand what other people say even if you don’t agree with them, just for the sake of understanding. 

Yehuda: Yeah, nobody out there is that radical of a pluralist when it comes to ideas and knowledge. Because if you’re that radical, you don’t hold any commitments, in which case that’s not interesting either. Right?

I mean, David Hartman wrote about this once in a volume that was collected by Rabbi Jonathan Sacks, where he says something to the effect of like, “If I don’t talk to people who I disagree with, how will I convince them that they’re wrong?”

Jonathan: Right. 

Yehuda: That’s like a laugh line. But then he goes on to say, “I also am aware that in that encounter there’s a possibility, a risk, that I will have my own viewpoints changed, but I choose to put myself in that environment of risk,” and he has a whole variety of reasons to do so. 

Jonathan: Yeah, I totally agree with that.

And like, this is what I was trying to go back to in the Rav Kook idea of the achdut ha-hafachim, is that even if I’m not going to radically change my mind and adopt somebody else’s philosophy, I can see truths in somebody else’s philosophy. It’s not zero sum. I might still believe what I believe in, but you know what? Hey, I hadn’t thought about a point that you’re making. I feel like I’m a better person having heard what you said and adopted something I would not have adopted into my sort of like view of life in a way that I feel grateful to you for having shared that with me. I don’t think I would’ve thought of that if, had I just remained in the algorithmic echo chamber.

Yehuda: Yeah, even though you haven’t necessarily altered your major life choices as a result. 

Jonathan: Yeah. Correct. 

Yehuda: So I did the closing charge a few weeks ago at the Hartman Teen Fellows Shabbaton, and I, the question I got, I got it more directly from the students, which was, “What do you want from us?” Like, what are you hoping for us in the world? 

And it was actually, like it really gave me pause. You know, of course, part of me was like, “We have great ideas. We want you to embody them,” but we’re not a denomination, and I actually want the Orthodox kids to not feel like I have to change denominations and join this Hartman one. I want them to be serious Orthodox kids, and that’s ultimately what I said. 

I said, “Whatever kind of Jew you are, I want you to be the most serious version of it.” 

And that includes, right, integrating the relationships that you have with others, making informed, serious Jewish choices, affirmed choices, and continuing to learn. That’s like a big piece of what it is to be.

But it is more specific in an Orthodox school. And I know you did at the senior Shabbaton a discussion with your students on what does a… I heard it was, “what does an ideal graduate look like?” but I know that’s not what you said. It was, “what does a successful graduate look like?” 

And I’d love for you to talk a little bit about that, because it’s not just what you said in the speech at graduation. That’s only one piece of this. So what does a successful graduate look like? 

Jonathan: That’s a great question. I’ll point out something interesting. We do get feedback sometimes. We got this from, as you referenced, we had a Shabbaton the weekend right before graduation, and we talked about what does a successful SAR graduate look like? What are sort of, sort of final messages we’d like people to take with them? 

And we had a number of staff members who shared. One of the things that emerged after that conversation that we heard from some students is, “We like it when you tell us specifically what you want us to do.” As I said to people, yeah, I think you like that now because you didn’t get that so strongly beaten over the head with this is what you’re supposed to do to. So there’s always something of a, you know, a waxing and a waning of how you manage that. 

I became very enamored over the past year or so, I’ve been reading a lot, there’s a guy named Barry Johnson. Barry Johnson wrote a book called Polarity Management. It’s about business management. It’s not necessarily about schools or about religion, but I have come to believe that it’s the answer to every single question that exists in life.

He talks about polarity management, that, like, the problem that many businesses have, and I think also many schools and any organization has, is seeing issues as a problem to be solved rather than as a polarity to be managed. So for example, in schools, there’s always the tension between do you care more about the individual student or more about the community of students?

And it’s not an answer. There’s no answer to that question. You’re always gonna have to manage the tension between two sort of points that are always going to be in tension. There’s no solution. You’re always figuring out how to optimize the management of going between those two poles. You never want to lean too much in one direction because those things are ultimately part of life and part of what’s intention.

So I think also in an institution, giving kids freedom and giving kids guidance is not a problem to be solved, but a polarity to be managed.That being said, I think sometimes we do err on the side of giving freedom and opening up people to ideas. I think that sometimes, you know, it’s important for us to also take into account and realize we have to also be telling kids what we think they should be doing, what we hope for you, what we believe is a life that will bring you great joy and fulfillment, and this is what you should be doing.

This comes up when we’re teaching things like Halakha. Like, you’re teaching Halakha, you know, at some point, it’s like, it’s much easier to teach pluralistic openness to ideas when you’re learning Gemara. 

Yehuda: Sure. 

Jonathan: Rav Kook talks about that in his achdut ha’afachim, and I think Tal mentions that in his book as, like, the Gemara as a template for, you know, hearing different debates. When you get into actual practice, I don’t have the luxury of saying, this is okay. Look, what am I supposed to do? Please tell me, Rabbi. So that comes up sometimes. And I think that as a school, we set those standards, set those expectations, and sometimes a lot of kids want some more of that than I think we give them. 

I once heard a teacher of mine say that people should be much more focused on the vertical axis than on the horizontal axis of ideas. And what he meant when he said that was these sort of hot topics that create a lot of tension and heat and almost anger that divide us between left and right, whether it be political or he’s speaking more religiously within our Orthodox community, is often much easier and more fun, and it draws more people in.

His argument, which I found very compelling, was to stop focusing too much on the horizontal, looking at the other, but to actually figure out where you are and do what you believe in maximally, more vertical axis than horizontal axis. 

And so I believe that every student, when he or she comes into SAR as a ninth-grader, comes in as a particular place, they should feel like they have grown religiously, intellectually, academically, socially. Wherever you start out, you have to have been at a constant rate of growth, and you should be improved, which means that by definition, every single person comes in somewhere else, so every single person is different. So there’s no such thing as ideal. What is, I think, uniform is that everybody should be engaged in that process of growth and development on all of those different planes.

Now, I will also say, I hope that the graduates of our school have bought into and will continue to buy into the school’s commitment to a modern Orthodox Hashkafa, a modern Orthodox worldview, which is to say there’s a strong commitment to Halakhic practice. There’s a strong commitment to Am Yisrael. There’s a strong commitment to Medinat Yisrael. There is total involvement in seeing your Jewish identity not as the second part of who you are, but as the primary part of who you are. And respecting everybody makes different decisions. 

We talked at that panel about students who have made decisions to go outside of what we’ll call the modern Orthodox community. To the left is one way, but also to the right. Both those things happen. 

Yehuda: Yep. 

Jonathan: Somebody raised the question, “Would you be proud of those people?” I found that to be like a, like an interesting question, but also I didn’t like the question, ’cause I felt like proud of… like, you guys make your own decisions. Like, I feel bad that somebody wants almost like their validation from me, a grown-up in their 30s. I wasn’t sure if I liked or didn’t like that they wanted to know whether I was proud of them, if they were to ask that question. 

Yehuda: But you know, though, what that’s about. They’re asking about whether you love them.

Jonathan: Yeah. So they—

Yehuda: And that’s what they’re really asking. 

Jonathan: Yes, 100%. So I tried to say, I love you. I think you’re the greatest. You are a grown-up, you are an individual, you’re gonna make decisions. If you make decisions that are different than decisions I chose in my life, I can, like, live with that. I love you. You’re great. I may not hold you up and bring you back as an alumni speaker to share with the students, like, what I hope you would aspire towards, ’cause there are things we believe in. 

That being said, you go far to the left, far to the right, I love you. You’re great. You make decisions. You have autonomy and agency, and, like, that’s great and terrific.

Of course, again, I would feel very differently, if the majority of our students didn’t buy what we were selling here, I’d have to go back and rethink the whole project. I think that’s true. 

Yehuda: Yeah, in some ways, what you’re saying is, I’m not gonna change. I, Jon Kroll, I have my commitments. This is what I believe in. This is what I’m trying to convince you of these commitments. And maybe even some of the successes, wherever you wind up going, I want to be in your head so that the choices that you’re making are in relationship to the things that you learned, right? And they’re not a radical rejection of the sincerity of the things that you were taught.

Jonathan: Yeah, I think that that’s a fair description of it. I would love to take a look at the numbers of this. I’m not sure whether there are more kids who have moved far to the right or far to the left amongst our graduates. I really don’t know the answer to that question or how many people are sort of, like, within, what we’ll call our spectrum within this world. I’m not sure I know the answer to that question. I do think it’s a really interesting question. 

And I look at these kids, and it’s like, okay, I love you. You’re fantastic. The kids who are learning in Haredi yeshivas, like, yeah, I hope that you will look with fondness upon your experience at SAR when you learned here. I hope that you will experience what you learned. I hope you will experience certain commitments to Judaism, the Jewish people, Israel, that you will take seriously as who you are, to the kids on the right and the kids on the left as well. 

Yehuda: Yeah, I think that one of the things that afflicts me a little bit about this in the Orthodox educational system is, and this is a little bit old data. I don’t know what’s changing. A lot of this stuff is changing very fast. Post-October 7th, I think student behaviors are very different. 

But there was some good data for a long time that when, there’s always drop off from one denomination to the other, right? But when a Reform Jew becomes less observant, they still call themselves a Reform Jew. When a Conservative Jew changes their practice, they may identify as a Reform Jew or something else. But when people leave Orthodoxy, not becoming Charedi, but becoming not-Orthodox, not observant, that is the highest risk of going from one denomination to none, is actually from Orthodoxy. 

And one of the reasons I’ve always hypothesized about this is because the Orthodox schools are not invested in giving their kids a ladder. They don’t wanna say, “If you’re not Orthodox, you could be Conservative, or you could be Reconstructionist.” They’re not invested in that because they don’t wanna give choice. But it leaves this possibility that someone will say, “I can no longer adhere to the commitments that I was taught for X, Y, Z reasons, and now my only option therefore is to be not connected to my Jewishness.” And that makes me worried. 

Jonathan: That might be true. I could also, again, I haven’t really thought about it all that much, but I would hypothesize another hypothesis. It’s almost like the opposite of what you’re suggesting, which is that I think you find this sometimes within the more Masorati community, amongst Sefardim in Israel, which is the Judaism that I’m not choosing to practice is the Orthodox Judaism.

Yehuda: Is Orthodox. Yeah. 

Jonathan: When I go to shul, I’m gonna go to the Orthodox shul, but I don’t really believe in, in this stuff so much. I suspect there’s a piece in that as well, but I, I’m not entirely sure. 

Yehuda: Yeah. As a parent, Stephanie and I talk about this all the time, we have kids in multiple day schools, as you know, and we always talk, both with ourselves and even with our kids about the fact that ultimately, I don’t know what it is, 85, 90% of what’s taught in the school we’re all in line with. And then there’s probably 10 or 15%, and part of the responsibility of parents is to do some counter-educating to the school. 

And I actually think that’s even a low percentage relative to Jewish history, given the fact that for most of our history, the expectation was the primary teachers of Judaism to their children were parents. Schools were not the apparatuses that they once were. That’s where the mitzvah lies. Like, it’s a mitzvah for you to teach my children only ’cause I’ve asked you to. 

Jonathan: Correct. 

Yehuda: Right? My responsibility is here. 

What do you think about when it comes to how the school recognizes, understands that there’s counter-education taking place, actually on multiple value systems by parents all the time as the school is teaching its curriculum?

Jonathan: Yeah, 100%. I liked the idea of giving our school a lot of credit for our students’ successes. That makes me feel good. But when I look in the mirror or when I think about what the reality is, what is the extent To which a parent’s home, the influence that kids have outside of school makes them who they are versus the percentage of what happens inside of school makes them who they are. 

This is my job. I get, like, a salary to make sure the schools have that kind of impact. I think the biggest influence is the family that one grows up in is far, you, you talked about, you know, 85% you might agree with the school and 15% you might not agree. Yes, I totally buy into that, and I think that’s true, and I think every family will have something like that. I’m not sure that every family is gonna be as intentional as you and Stephanie might be about recognizing what that is and intentionally sort of, like, conveying messages to your kids about that. 

I think in a parallel sort of way, I look at, I’m not sure what the numbers are. I feel like if you have asked me to quantify, feels like shaping who students are, I don’t know, 75%, it’s like what goes on in the home and who the parents are and the upbringing and, and school can enhance that or can mess things up a little bit with kids. We can give them a great education and help them learn ideas, but in terms of, like, their core sense of selves, who they are, we can make it a little bit better, and we can make it a little bit worse on the margins. 

But I think so much of that is the partnership between parents and kids. And who kids are is so much more seriously defined and foundation of what their family’s like and what the messages that their parents and their friends are giving them. 

Yehuda: Yeah. I have a thousand things I wanna ask you, but ask you one more big question, and it’s a complicated one. Obviously, the best thing that you said in your speech was when you said to the kids, “Please consider a career in Jewish education.”

So I don’t know if you noticed, like, there was tepid applause, but some of us in the balcony were going nuts. That was, like, the best line. 

Jonathan: Oh, that was you? 

Yehuda: And the faculty section was—that was us. 

Jonathan: I heard somebody in the balcony hooting and hollering. 

Yehuda: Oh, yeah, we were … That was us. 

Jonathan: Oh, okay. 

Yehuda: Of course. Like, you have to say that over and over again, like, choose careers with values. I’ve said this before, I think, but my kids, our boys staged an intervention with us a few years ago where they were like, “We feel pressured by you guys to have meaningful careers.” And I was like, “Correct.”

Jonathan: Good. 

Yehuda: “Correct.” I was like, “I’m not dictating what it is, but it is correct.”

But there was also this weird undercurrent of like—because of the socioeconomic realities of being a modern Orthodox Jew, because of, as one of my kids said to me recently, he was like, “Yeah, there’s only really four options that are seriously thought about for people in this community, and it’s pervasive, which are finance, real estate, law, and medicine, but less and less medicine.” That’s it. 

And it even came across in, like, the little student bios that you do of, like, how many kids where it was referenced that they were going into careers in finance. I was like, it was, like, mind-boggling. At 18. What do we do about this, Jon? Like, we are in a crisis for our people about talent and continuity and the pipeline, and this, you can only give your life to it with a sense of mesirut nefesh, that I’m actually sacrificing something in an environment where you know that the struggle will be very different.

How does the school take this on, especially when it’s also the hand that’s feeding you, right, in constructing the community? 

Jonathan: Yeah, absolutely. For the past three years at graduation, I’ve included a message like that, and I will continue to do so every year because I think it’s the kind of thing that needs a little bit more indoctrination as that being something that is a real value and people should think about it seriously.

I’ll tell you a funny anecdote. After the speech, after graduation that night, I got an email from a, I will not say his name, I got an email from a graduate of SAR High School from a few years ago who was in the audience, and he said, “Thank you so much for saying that. I want to go into chinuch and my parents are very hesitant about allowing me to do so, and this made me feel like you gave me more permission to have a serious conversation with my parents about choosing this as a career,” and the kid thanked me. 

I wasn’t thinking about him when I gave my speech, but that’s great. There’s nothing more powerful than being able to hire, as teachers in your school, graduates of your school. Unbelievable. We have a few of them, and it’s, like, so powerful, and it’s such a great statement. 

I do feel like, delivering the message. I’m hoping to get a few kids who will go, go for it. I’m not worried, Yehuda, about having all of a sudden drying up any sort of tuition dollars because everybody’s going into chinuch now. 

Yehuda: Right. I’m not worried about that either. 

Jonathan: Halevi. No, like, that’s not my concern. I do think, though, that there are plenty of people who would really have meaningful lives contributing to the Jewish community, whether it’s in a school like SAR, whether it’s in Jewish communal life in other ways, and there are ways that you can make ends meet in a way that is dignified, and I like having those conversations with kids about that.

But it is mesirut nefesh. You could probably make a lot more money and have a more comfortable lifestyle if you are going into other professions. That being said, I noticed there wasn’t, like, raucous applause at the “go into Jewish education.” I do think, though, that when I talk about this with kids, I don’t only say it at graduation. I try to deliver that message, pepper it throughout conversations I have throughout the regular school year. Kids see the value in it. 

And I get into real practical things, like there are tuition discounts for people who go into education. People work in summer camps, and that is not just a way of making a few more bucks. It’s a lifestyle that is very wonderful for raising children if you work in a summer camp. And there are lots of things about the lifestyle that are not pure mesirut nefesh. There are aspects of this mesirut nefesh, but it also is many ways like a real, great lifestyle choice. 

Yehuda: Yeah. Yeah. Well, there’s a lot more to say about that in terms of what we need to do in terms of our community itself and its values, but for another time.

The only last decent question one asks of a principal or a teacher is what are your plans for summer vacation? 

Jonathan: Oh, well, I have great summer plans. I have a daughter who lives in Israel who will be having, she’s in her eighth month of pregnancy right now.

Yehuda: B’sha’ah tovah.

Jonathan: So my wife and I are planning on being in Israel for a few weeks there, mid-July and August, and I also have a third child who’s getting married at the end of August. So good simchas in the Kroll family. 

Yehuda: Amen. Jews should have many more. Thank you for your leadership and thanks for coming on the show. 

Jonathan: Thank you, Yehuda. Thank you. Really appreciate it.