OTD, Datlash, and the Religious Spectrum: When Orthodox Jews Leave Orthodoxy with Rabbi Alex Israel (CLASSIC EPISODE)
Release Date: 04/21/2025
Emergency Episode: The U.S. Attacks Iran — What It Means for Israel, Hamas, and the Future of the War (252)
Orthodox Conundrum
When the United States bombed Iran’s nuclear sites this week, the Middle East—and the world—entered a new phase of conflict. In this urgent episode, Scott speaks once again with Yaakov Katz, former editor of The Jerusalem Post, about what these strikes mean for Israel’s war effort, the potential consequences of regime change in Iran, the risks of escalation, and how this moment may redefine the geopolitical landscape. This is essential listening for anyone who wants to understand what’s really happening beyond the headlines. Check out the Tehillim Unveiled Podcast! Their episode on...
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The New Face of American Antisemitism: Violence, Politics, and Denial (BONUS EPISODE)
Orthodox Conundrum
Two Israeli embassy staffers shot in Washington. Jewish activists burned in Boulder. A mayoral candidate in New York who refused to condemn the Holocaust gaining momentum. Antisemitism in the United States is no longer hiding in the shadows — it’s on the march, in broad daylight. In this urgent bonus episode of Orthodox Conundrum, Scott Kahn speaks with Rabbi Chaim Steinmetz and Andy Weiss about the troubling rise in antisemitic violence and rhetoric, the mainstreaming of hate, and how American Jews are responding — with concern, activism, and a growing sense of alarm. From Zohran...
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Unscripted Reflections: Israel, Iran, and the Challenge of Faith in Wartime (251)
Orthodox Conundrum
In this spontaneous and unfiltered episode of Orthodox Conundrum, Scott shares heartfelt reflections on Israel’s war against Iran—not from a political or military perspective, but through personal experience and the lens of faith. What does it mean to believe in Divine providence during a time of fear and uncertainty? How should we grapple with the moral and spiritual implications of war? Without a script or agenda, this episode wrestles with the difficult questions that arise when religious conviction meets the harsh realities of conflict. Check out Orthodox Conundrum Commentary on...
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What Comes Next? Yaakov Katz on Israel’s War, Netanyahu’s Calculations, and the Search for an Endgame (250)
Orthodox Conundrum
Twenty months into the war with Hamas, many Israelis and supporters abroad are asking the same urgent question: how will this end? In this in-depth episode of Orthodox Conundrum, Scott Kahn is joined by Yaakov Katz, one of Israel’s most respected journalists and author of While Israel Slept, to examine whether Israel’s military goals are still realistic — or even defined. They discuss the uncertain state of the war, Netanyahu’s political maneuvering, the role of the Chareidi parties, international pressure, and the trust gap between the government and the public. It’s a sobering...
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From Beit Lechem to the Royal Ball: Comparing and Contrasting the Book of Ruth and Cinderella, with Rabbi Dr. Joshua Berman (249)
Orthodox Conundrum
Megilat Rut — the Book of Ruth — is one of the most beloved and widely read books in the Hebrew Bible. Because we read it annually on Shavuot, many people are familiar with its basic storyline. But its very familiarity can sometimes obscure its most powerful messages. In this episode, I’m joined by Rabbi Dr. Joshua Berman of Bar Ilan University, who offers a fascinating lens through which to revisit Ruth’s story: the world’s most popular fairytale — Cinderella. By comparing the two narratives, Rabbi Berman uncovers striking parallels and, more importantly, profound differences that...
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Can Physics Demonstrate God's Existence? (248)
Orthodox Conundrum
Can science be a vehicle to get closer to God? The Rambam famously answered in the affirmative. In the second of the 1000 chapters of his Mishneh Torah, Hilchot Yesodei HaTorah chapter 2, the Rambam writes, “What is the method towards loving and fearing God? At the moment that a person investigates His wondrous and massive actions and creations, and sees through them His endless and infinite wisdom, he immediately loves, praises, and extols, and desires tremendously to know the great Name. In the words of David, ‘My soul thirsts for God, the living divine.’ And when he thinks about these...
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Having “The Talk”: How Should Jewish Parents Talk to Kids About Sex? (Co-produced with Intimate Judaism)
Orthodox Conundrum
Please note that this episode discusses sensitive topics and uses explicit language. Listener discretion is advised. Today, the Orthodox Conundrum is releasing a new episode of Intimate Judaism that my Intimate Judaism co-host, Talli Rosenbaum, and I recorded with Yonina Rubinstein, where we explore how parents can approach conversations about sexuality with sensitivity, clarity, and confidence. How can we talk to kids about sex in a way that’s honest, healthy, and grounded in Jewish values? Yonina offers practical strategies for different ages and stages, explains the importance of modeling...
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The Pope, the Jews, and Israel: What to Anticipate From Pope Leo XIV, with Dr. Malka Simkovich (BONUS EPISODE)
Orthodox Conundrum
Last Thursday, Cardinal Robert Prevost of Chicago became Pope Leo XIV. While Jews may believe that this shouldn’t matter to us at all, this is most likely false. The pope commands the allegiance of well over a billion Roman Catholics worldwide, and his ability to help shape their opinions about the Jewish people and Israel should not be underestimated. To discuss what his election means for the Jewish people, and to review his predecessor Pope Francis’s record towards Jews and the Jewish state, I was honored to speak to Dr. Malka Simkovich. Malka has an interesting vantage point, as she is...
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"You Can't Suppress the Light": The Radical Messages of Rav Kook for Orthodox Jews Today, with Professor Marc Shapiro (247)
Orthodox Conundrum
The thought of Rav Avraham Yitzchak HaKohen Kook, who died in 1935, remains extremely influential today in religious Zionist circles. Rav Kook’s ideology, particularly as interpreted by his son, Rav Tzvi Yehuda Kook, in books like Orot, has helped to set the agenda for much of the dati leumi world. Over the past couple of decades, however, additional works written by Rav Kook have been published, and some of the ideas they contain are extraordinarily fascinating and at times radical, even as they often have little to do with the Land of Israel or Zionism. These ideas, far from being dated,...
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Inside the Real Rules of War: Colonel John Spencer vs. Media Myths About Israel and Hamas (246)
Orthodox Conundrum
Colonel John Spencer, one of the world's leading experts on urban warfare, joins me for a wide-ranging conversation about Israel’s war against Hamas. We dive deep into the realities of modern combat, the strict standards of international law, and the false accusations of "genocide" being leveled against Israel. Colonel Spencer also shares insights from his recent high-profile debate alongside Dave Smith on Piers Morgan Uncensored, where he pushed back against the misinformation dominating media narratives. We talk about the dangers of influencer-driven disinformation, the moral challenges...
info_outlineThe Orthodox Conundrum Podcast is off this week, and we'll be back next week with a brand new episode. In the meantime, enjoy this classic episode about Orthodox Jews who leave Orthodoxy.
There’s a phenomenon in the Orthodox world which is called by various names, though most commonly “Off the Derech” or OTD, and “Datlash,” short for “Dati Leshe’avar” - that is, formerly religious. For a community which prides itself on continuity and on passing the tradition from one generation to the next, the idea that people leave Orthodoxy is simultaneously painful and threatening. Why did he or she leave? What didn’t work? Why don’t they see what I see… or perhaps, if we’re being truly honest with ourselves, what do they see that I may be missing? And when the people who reject an Orthodox way of life are members of our family, the difficulties are compounded.
Rabbi Alex Israel has given a lot of thought to this issue and these questions, and his insights are humane, generous, and rooted in Torah. Rabbi Israel and Scott spoke about whether the terms OTD and Datlash - and even “dati,” religious - are helpful or misleading, whether the phenomenon of people moving away from Orthodoxy is becoming more common, how it may be different in Israel and in the United States, whether we should actively try to bring those who have left Orthodoxy back into the Orthodox fold, if an emphasis on dogma is partially to blame, how parents should navigate having a child who is less religious than they are, what we can learn from those who leave Orthodoxy, and more.
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