OTD, Datlash, and the Religious Spectrum: When Orthodox Jews Leave Orthodoxy with Rabbi Alex Israel (CLASSIC EPISODE)
Release Date: 04/21/2025
Hostility, Confusion, and Ideological Pressure: Outreach in a Changing World, with Rabbi Mark Wildes (269)
Orthodox Conundrum
Zohran Mamdani - a politician who openly rejects Israel’s right to exist as a Jewish state, yet insists that this has nothing to do with antisemitism - is now the mayor-elect of New York City. He points to a small number of Jewish supporters as evidence, while promoting a worldview in which Israel is framed as a genocidal, apartheid project. New York is home to the largest Jewish community in the diaspora. When that city elects a proudly anti-Zionist mayor, it sends a message far beyond one municipality. It raises hard questions: What does it mean for Jewish security, for public discourse...
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Mamdani, Fuentes, Tucker, and Mainstreaming Antisemitism: Jonathan Greenblatt on the Growing Threat from the Left and the Right (268)
Orthodox Conundrum
In recent weeks we have watched something many of us hoped we would not see in the United States: openly anti-Zionist and even openly antisemitic voices moving from the margins into the mainstream. Zohran Mamdani’s victory in New York raises the chilling possibility that hostility to Israel is now an electoral asset. At the same time, parts of the American right are flirting with figures like Nick Fuentes, a Holocaust denier who says Jews do not belong in Western civilization. To make sense of this moment, I spoke with Jonathan Greenblatt, CEO and National Director of the Anti Defamation...
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Charedi, Dati Leumi, Modern Orthodox, Traditional, Secular: Is Jewish Unity Even Possible? A Conversation with Rav Yosef Zvi Rimon (267)
Orthodox Conundrum
Is Jewish unity even possible? In this urgent episode Rav Yosef Zvi Rimon faces the hardest questions raised by the draft crisis and by the widening gaps between Charedi, Dati Leumi, Modern Orthodox, Traditional, and Secular Jews. He explains why unity is not a slogan but a practical necessity and religious obligation with real consequences for security, community, and our shared future. With clarity and empathy he maps a path for principled disagreement, mutual responsibility, and practical steps that families, shuls, and schools can take right now. If you are tired of talking points and want...
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The World is a Beautiful Place... and We Need to Earn It: Talking About The Morning After with Dr. Erica Brown (266)
Orthodox Conundrum
What does the morning after really look like... when the dawn reveals not only light, but rubble and work? In this deeply personal conversation, Scott and Dr. Erica Brown ask how we craft a vision of where we’re going when optimism feels naïve, unity is fragile, and joy and grief insist on sharing the same space. Drawing on Rabbi Sacks’s distinction between optimism and hope, they explore how to build active hope through autonomy, giving, and purpose. They define Jewish unity as purposefulness rather than groupthink, wrestle with isolation and rising antisemitism in the diaspora, and...
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Seven Facets of Healing: Rabbi Leo Dee’s Blueprint for Jewish Resilience (265)
Orthodox Conundrum
This episode is dedicated to the complete recovery of יהונתן איתן בן בת שבע ברכה. How do we move from private anguish to collective strength? In this deeply personal and wide-ranging conversation, Rabbi Leo Dee shares the story of the day his wife and two daughters were murdered, and the seven-facet framework he built to keep living with faith and purpose. We walk through Family, Friends, Fitness, Frumkeit (spiritual life), Function (purpose), Finances (trust and control), and Fun (simcha/growth)... first as practices for an individual in pain, and then as a national...
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Eulogies and Boundaries: Orthodox Jews and the Legacy of Charlie Kirk (264)
Orthodox Conundrum
Charlie Kirk’s assassination is a shocking, tragic act of violence. Murder is a desecration of the image of God, full stop. We condemn it unequivocally, and we pray for comfort for his family and for all who were harmed. At the same time, Charlie Kirk was a complicated public figure. He was outspokenly pro-Israel and often advocated for Jewish safety; he also voiced criticisms of Israel’s current government. He advanced positions that many in the Orthodox world consider essential, and others consider deeply problematic. He defended Israel vigorously, and he also gave a platform to voices...
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God's Loyal Opposition: Anger, Faith, and Divine Confrontation, with Rabbi Dr. Raphael Zarum (263)
Orthodox Conundrum
Is it possible—maybe even Jewish—to be angry at God? From Abraham’s challenge at Sodom to Job’s cries of despair, Tanach is filled with voices that confront the Divine. But what does that mean for us today, when we struggle with personal tragedy, global antisemitism, and the ongoing pain of the seemingly endless war against Hamas? In this wide-ranging conversation on the Orthodox Conundrum, Scott Kahn speaks with Rabbi Dr. Raphael Zarum, Dean of the London School of Jewish Studies, about whether anger at God is heresy or a profound act of faith. Along the way, they discuss biblical...
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Suppressed, Rediscovered, Essential: Rav Kook’s Lost Guide for Modern Faith (262)
Orthodox Conundrum
This episode is partially a detective story, partially an analysis of daring ideas, and partially an invitation to discover new methodolgies of confronting challenges to Orthodox Judaism. Rav Kook drafted L’Nevuchei HaDor over a century ago—then the manuscript largely disappeared from view, resurfaced piecemeal, and sparked debates about redaction and “censorship.” In this follow-up to our popular episode with Professor Marc Shapiro, I speak with Rabbi Aryeh Sklar, translator of the new English edition, to unpack both the history of the text (why it was sidelined, what changed between...
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Learning Tanach Daily Through 929: Opportunities, Challenges, and Dangers, with Rabbi Benny Lau (261)
Orthodox Conundrum
As one 929 cycle ends and the next begins, Scott talks with Rabbi Benny Lau—founder of 929—about why the project started, what it hopes to change in Jewish life, and what a shared, chapter-a-day cadence can build across communities. They also tackle the harder questions: the risks of using Tanach as a direct guidebook without the mediating lens of the Oral Tradition, how to engage ethically with challenging passages, and where pluralism meets red lines. Practical takeaways included: how beginners can start this week, and what to do when you fall behind. Whether you’re all-in on 929 or...
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Orthodox Parents and Their LGBTQ Children, with Rabbi Yakov Horowitz (260)
Orthodox Conundrum
When a child shares something deeply personal about his or her sexual orientation, Orthodox parents can feel love, concern, and uncertainty all at once. In this conversation, Rabbi Yakov Horowitz reflects on what he’s learned working with families and communal leaders: how to approach the first conversations, which words can prevent hurt, and where halacha and mesorah guide our choices. We also consider what he’s heard from senior rabbinic figures, how different communities navigate these moments, and what hope might look like over time. This is a tender, honest discussion meant to help...
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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