Orthodox Conundrum
The Orthodox Conundrum is a forum in which we look honestly at the Orthodox Jewish community, identifying what works well and what does not, so that, through an honest accounting, we can find solutions that will be successful. We will examine some of the major issues that affect the Orthodox world, without exaggeration, whitewashing, or pretending that they don’t exist. Our hope is that the Orthodox Conundrum will spark wider discussion that will enable Orthodox Judaism to continue moving forward in the areas at which it excels, and to rectify the areas that need improvement.
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Suppressed, Rediscovered, Essential: Rav Kook’s Lost Guide for Modern Faith (262)
09/08/2025
Suppressed, Rediscovered, Essential: Rav Kook’s Lost Guide for Modern Faith (262)
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 versions, and who may have been protecting whom) and the ideas that make it urgent now: how Rav Kook navigates tensions between moral intuition and Torah; his approach to challenges from writings of the ancient Near East; why heresy can refine faith; his respectful stance toward other religions; and much more. As we approach Rosh Hashanah and Yom Kippur, we ask what this early, daring Rav Kook can offer a polarized 2025 about creative teshuva, intellectual honesty, and religious confidence without fear. Check out the wonderful new podcast, Women Talking Mitzvot, co-produced by Deracheha.org and Beit Midrash Migdal Oz, with Rabbanit Shayna Goldberg and Rabbanit Dr. Yosefa Fogel Wruble. To listen, (Apple) or (Spotify). We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. () No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Learning Tanach Daily Through 929: Opportunities, Challenges, and Dangers, with Rabbi Benny Lau (261)
09/01/2025
Learning Tanach Daily Through 929: Opportunities, Challenges, and Dangers, with Rabbi Benny Lau (261)
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 cautious about it, this episode is about reading Tanach deeply—and responsibly. Check out the wonderful new podcast, Women Talking Mitzvot, co-produced by Deracheha.org and Beit Midrash Migdal Oz, with Rabbanit Shayna Goldberg and Rabbanit Dr. Yosefa Fogel Wruble. To listen, (Apple) or (Spotify). We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. () No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Orthodox Parents and Their LGBTQ Children, with Rabbi Yakov Horowitz (260)
08/24/2025
Orthodox Parents and Their LGBTQ Children, with Rabbi Yakov Horowitz (260)
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 listeners think carefully, speak gently, and consider their next steps with dignity—whatever they may be. Check out Tehillim Unveiled with Ari Levisohn and Rav Jeremy Tibbetts on or on - with a new three-part series on Tehillim 27, L'David Hashem Ori, dropping just in time for Elul! To contact Kesher Families, . Follow Rabbi Yakov Horowitz on Instagram - and . We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. () No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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When Mitzvot Lose Their Meaning: Rabbi David Stav on Reconnecting Orthodox Youth to Jewish Law (259)
08/18/2025
When Mitzvot Lose Their Meaning: Rabbi David Stav on Reconnecting Orthodox Youth to Jewish Law (259)
Why do so many young Modern Orthodox and National Religious Jews embrace the community but drift from halacha? In this episode of Orthodox Conundrum, Rabbi David Stav, head of Tzohar, joins Scott to confront the growing gap between identity and observance. Together they tackle the hard questions: Are we teaching halacha in ways that feel lifeless and irrelevant? Has secular society — from college to army service to technology — reshaped how youth see mitzvot? And most importantly, how can parents and educators reignite passion for Torah and halacha, showing a new generation that Jewish law is not just obligation, but a path to joy, meaning, and belonging? Check out the wonderful new podcast, Women Talking Mitzvot, co-produced by Deracheha.org and Beit Midrash Migdal Oz, with Rabbanit Shayna Goldberg and Rabbanit Dr. Yosefa Fogel Wruble. To listen, (Apple) or (Spotify). We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. () No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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The Bible, the Beasts, and the Big Lies About Israel, with Rabbi Dr. Natan Slifkin (258)
08/11/2025
The Bible, the Beasts, and the Big Lies About Israel, with Rabbi Dr. Natan Slifkin (258)
From biblical lions to the bizarre “Zionist crocodile plot,” Israel’s wildlife tells a story that shatters modern anti-Israel myths. In his new book Lions of Zion, Rabbi Dr. Natan Slifkin reveals how the animals of the Land of Israel — past and present — reflect the Jewish people’s deep, indigenous connection to their homeland. Scott and Rabbi Slifkin tackle false narratives about “settler colonialism,” “greenwashing,” and cultural appropriation, and explore how creatures like sunbirds, jackals, and even poppies have been weaponized in the propaganda war against Israel. This eye-opening conversation blends Bible, zoology, and politics to show that in Israel, even the animals have a story to tell. To order The Lions of Zion: Biblical Natural History and the Significance of Israel, We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. () No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Disagreeing Like Moses: A Torah Blueprint for Conflict Resolution (257)
07/28/2025
Disagreeing Like Moses: A Torah Blueprint for Conflict Resolution (257)
As we approach Tisha B'Av — a day that mourns the devastating consequences of internal strife and baseless hatred — we must ask: is there a Torah model for constructive conflict resolution? Rabbi Alex Israel joins Scott to explore a striking example in Bamidbar chapter 32, where Moses engages the tribes of Reuben and Gad in what Rabbi Jonathan Sacks called, "a model illustration of positive negotiation and conflict resolution." What does this biblical conversation teach us about how to mediate conflict, preserve unity, and build a stronger community — even when we disagree? Scott and Rabbi Israel then apply these lessons to modern conflicts that divide the Jewish people in Israel and around the world. This episode offers a timely and hopeful message: disagreement doesn't have to lead to division, and conflict can become a source of growth — if we learn to listen, negotiate, and speak with respect. Check out the Tehillim Unveiled Podcast! Their episode on Tehillim 89 is especially relevant in the days leading up to Tisha B'Av - you can find it on or . We're excited to announce that we at Jewish Coffee House are continuing to expand the conversation by bringing you—our listeners—into the mix. Introducing JCH Q&A, an exciting new podcast where listener-submitted questions are answered in a thoughtful, honest, and engaging way. We plan to dive deep into your pressing hashkafic, political, and philosophical questions. We will address the ideas that matter, the issues that challange us, and the topics that spark real curiosity. To submit a question for our first episode, you must be a member of the JCH Podcast WhatsApp Community. () No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! To read my article on Jewish Unity from last month, . Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Must Every Jew Be Shomer Shabbat? A Fresh Perspective on Kiruv, with Rabbi Simi Lerner (256)
07/21/2025
Must Every Jew Be Shomer Shabbat? A Fresh Perspective on Kiruv, with Rabbi Simi Lerner (256)
What is kiruv really about—and what should it be about? In this thought-provoking conversation, Scott speaks with Rabbi Simi Lerner, a kiruv professional who challenges conventional assumptions about Orthodox Jewish outreach. They explore the core goals of kiruv, the philosophical and ethical pitfalls it can fall into, and how to ensure it respects the dignity and autonomy of every individual. Is the point to make people religious? Should every Jew be Shomer Shabbat? What happens when outreach causes regret—or even harm? They also discuss whether kiruv professionals objectify people, the bad habit exhibited by some kiruv professionals (and the problem with having "kivurv professionals"), and how to navigate halacha with integrity in the face of complex realities. Rav Simi emphasizes that many kiruv workers do tremendous and holy work in a careful and sensitive manner... and others do not. This is a candid and essential conversation about one of the most idealistic—and sometimes problematic—projects in the Jewish world. Check out the Tehillim Unveiled Podcast! Their episode on Tehillim 89 is especially relevant in the days leading up to Tisha B'Av - you can find it on or . Links for Rav Simi Lerner: Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Overeating, Obesity, Ozempic, and Orthodox Jews, with Dr. Sharon Grossman (255)
07/15/2025
Overeating, Obesity, Ozempic, and Orthodox Jews, with Dr. Sharon Grossman (255)
Obesity is now responsible for more deaths in the United States than smoking—yet the Orthodox Jewish community rarely addresses it as either a public health emergency or a halachic concern. In this eye-opening episode, Scott speaks with Dr. Sharon Grossman to explore the medical, hashkafic, and halachic dimensions of obesity, overeating, and eating disorders. They discuss startling statistics about caloric intake on Shabbat, whether extravagant kiddushes and wedding meals reflect a violation of Torah values, and how halacha approaches issues like achilat gasa, guarding one's health, and weight loss surgery. They also tackle the other extreme—unhealthy preoccupations with appearance, the dangers of anorexia, and the rise of drugs like Ozempic. Can Judaism offer a healthy, balanced view of eating, body image, and self-care? This conversation challenges us to rethink how we relate to food, our health, and our values. Jewish Coffee House - the company of which Orthodox Conundrum Commentary is a part - has plans to grow and provide additional exceptional content… and to do that right, we need your help. Our summer intern, Nathan Shapiro, put together a survey so that we can better provide the podcasts, articles, live events, and online presentations that will speak to you. We plan to produce content that will be meaningful, stimulating, and entertaining - and we need your input so that we can create the best possible version of Jewish Coffee House. We want to hear from you. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Will Charedi Society Face Reality? Dayan Yehoshua Pfeffer on Work, Faith, and the Future of the Torah Community (254)
07/07/2025
Will Charedi Society Face Reality? Dayan Yehoshua Pfeffer on Work, Faith, and the Future of the Torah Community (254)
Is the Charedi community prepared to confront the demands of real life—economic, civic, and national—or has it built a worldview that prizes withdrawal over responsibility? In this provocative and thoughtful episode, Dayan Yehoshua Pfeffer joins Scott to explore what happens when religious ideology collides with practical reality. Drawing on his influential Sapir essay and other writings, Dayan Pfeffer explains how parts of Charedi society have defined religious life through a lens that minimizes human effort and places near-exclusive trust in divine outcomes—an attitude that discourages participation in Israel’s workforce, civic institutions, and national service. But is this mindset sustainable in a modern state? And how do Charedi thinkers reconcile it with halachic sources, economic necessity, and lived experience? Scott and Dayan Pfeffer also delve into the social, theological, and ideological obstacles to change—particularly the way certain ideas have become "untouchable" within the community. Can Charedim pursue professional careers, engage with broader society, and still maintain fidelity to Charedi identity? Or does such a shift inevitably bring them closer to the Modern Orthodox world? This is a challenging, respectful, and essential conversation for anyone concerned about the future of Torah Judaism in Israel and throughout the world. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Faith, Prayer, and the Impossible: Rabbi Shlomo Brody on Emunah, Miracles, Reality, and the Power of Tefillah (253)
06/30/2025
Faith, Prayer, and the Impossible: Rabbi Shlomo Brody on Emunah, Miracles, Reality, and the Power of Tefillah (253)
In the wake of Israel’s stunning victory over Iran—an event many have called miraculous—Jews around the world are reflecting on the nature of divine intervention and the power of prayer. Can we, and should we, pray for miracles? In this deeply thoughtful episode, Rabbi Shlomo Brody joins Scott to explore the halachic and emotional dimensions of tefillah in desperate times. What does it mean to ask for something that defies natural law? Is there a spiritual cost to praying for impossible outcomes? And how should we respond when a loved one is terminally ill—when a cure seems impossible, but giving up feels like betrayal? They also tackle a more uncomfortable question: Does excessive reliance on prayer risk becoming a substitute for human responsibility—such as voting, civic engagement, or taking necessary action in the real world? Can asking God for a miracle ever become a way of avoiding the hard work of confronting reality? This wide-ranging and nuanced conversation explores how to balance faith, hope, and the knowledge that God can do anything, with realism and the recognition that He has discouraged praying for that which is outside the realm of possibility; when to pray for mercy instead of outcomes; and how to maintain emunah without falling into magical thinking. It’s essential listening for anyone grappling with what it means to live—and pray—with integrity in the face of uncertainty and crisis. Check out the Tehillim Unveiled Podcast! Their episode on Tehillim 20 is especially relevant today - you can find it on or . Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Emergency Episode: The U.S. Attacks Iran — What It Means for Israel, Hamas, and the Future of the War (252)
06/23/2025
Emergency Episode: The U.S. Attacks Iran — What It Means for Israel, Hamas, and the Future of the War (252)
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 Tehillim 20 is especially relevant today - you can find it on or . To preorder While Israel Slept by Yaakov Katz, click Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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The New Face of American Antisemitism: Violence, Politics, and Denial (BONUS EPISODE)
06/19/2025
The New Face of American Antisemitism: Violence, Politics, and Denial (BONUS EPISODE)
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 Mamdani’s alarming candidacy to the broader cultural shift that’s making Jew-hatred acceptable again, this is a frank and timely conversation every Jew needs to hear — whether or not you live in New York. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Unscripted Reflections: Israel, Iran, and the Challenge of Faith in Wartime (251)
06/16/2025
Unscripted Reflections: Israel, Iran, and the Challenge of Faith in Wartime (251)
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 Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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What Comes Next? Yaakov Katz on Israel’s War, Netanyahu’s Calculations, and the Search for an Endgame (250)
06/09/2025
What Comes Next? Yaakov Katz on Israel’s War, Netanyahu’s Calculations, and the Search for an Endgame (250)
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 but essential conversation for anyone who cares about Israel’s future. To preorder While Israel Slept, click Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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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)
05/26/2025
From Beit Lechem to the Royal Ball: Comparing and Contrasting the Book of Ruth and Cinderella, with Rabbi Dr. Joshua Berman (249)
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 highlight essential Torah values. This conversation will change how you read Megilat Rut and offer fresh insight into the values that give Jewish life depth, direction, and meaning. Listen to the Tehillim Unveiled podcast or wherever you find your podcasts. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Can Physics Demonstrate God's Existence? (248)
05/19/2025
Can Physics Demonstrate God's Existence? (248)
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 things themselves, he immediately recoils backward and is awestruck and fears, realizing that he is a small, lowly, and beclouded creature, with minimal and superficial knowledge compared to God’s perfect intellect. As David said, ‘When I see your heavens… what is man that You should acknowledge him?’ According to these ideas I will clarify important principles of the works of the Master of the worlds so that they will be an introduction to one who understands in order to love God. As the Sages said with regard to love, from this you recognize the One who spoke and the world came into being.” The Rambam then proceeds to give an introduction to the Aristotelian world view that was presumed true in his time. While we no longer accept the Rambam’s science as accurate, his principle that knowledge of the universe is a vehicle to loving and fearing God remains an essential principle. What about using science to demonstrate God’s existence? The Rambam, again, was willing to use philosophical arguments for this purpose; but others recoil from the concept. Many people have no interest in examining theories such as intelligent design and creationism, and find them absurd. There’s a different but somewhat similar phenomenon which Professor David Shatz calls “bold concordism,” where scientists attempt to demonstrate that the first chapter of Bereshit and modern physics are in complete agreement, as long as the words of the Torah are read in a literal, albeit non-obvious way. Some people find this inspiring and helpful, while others dismiss it altogether. My guests today, Rabbi Aaron Zimmer and Rabbi Dr. Elie Feder, propose something quite different. They use established scientific facts based on up-to-date physics - scientific facts, that is, which no one denies - and argue that the most logical conclusion from this science is that the universe was created by an intelligent designer. This has nothing to do with the argument of intelligent design from biology, and is not based on any verses in the Torah. It doesn’t even deal with questions around divine providence or other aspects of Jewish belief. Instead, they argue that modern physics has offered a brand new and extremely compelling version of the argument from design: that the values of the constants are so unusual and so inherently unlikely, that the most obvious conclusion by far is that they were designed so that our complex universe, which includes atoms, molecules, stars, galaxies, and life, would come into existence. As they explain, almost all serious physicists were bothered by the problem of why the constants are what they are; physicists almost universally acknowledge that the reason that the constants have the values that they do is a huge mystery. Elie and Aaron only differ with most other physicists in that many others try to solve this mystery by positing the existence of a multiverse - that is, infinitely many worlds, each with different values of the constants; whereas my guests argue that this is far more unlikely than the obvious answer: that something with intelligence chose these constants for a reason. Regardless of whether you like the idea of using science to demonstrate God’s existence or disagree with the enterprise, Elie and Aaron’s argument demands serious attention. I’m honored to present it today, and look forward to hearing what you think. To learn more about Physics to God, to listen to the podcast, or to watch it on YouTube, Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Having “The Talk”: How Should Jewish Parents Talk to Kids About Sex? (Co-produced with Intimate Judaism)
05/14/2025
Having “The Talk”: How Should Jewish Parents Talk to Kids About Sex? (Co-produced with Intimate Judaism)
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 a positive attitude toward intimacy, and discusses how halacha and tradition can serve as a guide—not a barrier—to raising sexually healthy children. Whether you’re a parent, educator, or just thinking ahead, this episode offers an essential roadmap for both navigating and redefining “The Talk” in a way that’s both open and deeply rooted in Jewish life. This episode is being released simultaneously on and the Orthodox Conundrum. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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The Pope, the Jews, and Israel: What to Anticipate From Pope Leo XIV, with Dr. Malka Simkovich (BONUS EPISODE)
05/12/2025
The Pope, the Jews, and Israel: What to Anticipate From Pope Leo XIV, with Dr. Malka Simkovich (BONUS EPISODE)
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 not only a well-known expert in Jewish-Christian relations, but she also spent ten years as the Chair of Jewish Studies at the Catholic Theological Union, which is where the pope studied in the early 1980s. This Tuesday night, the Orthodox Conundrum Podcast will release a regular episode - co-produced with Intimate Judaism - about how parents should talk about sex and intimacy with their kids. So look for that 48 hours after this bonus episode drops. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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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)
05/05/2025
"You Can't Suppress the Light": The Radical Messages of Rav Kook for Orthodox Jews Today, with Professor Marc Shapiro (247)
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, speak to Orthodox Jews today and often palpably address areas that concern us in 2025. Rav Kook addresses issues such as the limits of Talmud study in forming the religious character of yeshiva students, the importance of establishing a broad curriculum of both holy and secular studies in yeshivot, the possibility that following Jewish law may not be the highest form of spiritual achievement, the wisdom of the masses that at times supersedes that of scholars, the place of natural law and innate morality when it contradicts our understanding of the Torah, whether certain narratives in the Torah need to be taken literally or even may use the prevailing scientific assumptions of those who received the Torah in order to convey a deeper message, the possibility that other religions may be divinely inspired, and much more. I’m encouraged by thinkers who move boldly in directions that others are reluctant to go; the combination of absolute commitment to God, Torah, and the Jewish people alongside heroic courage and honesty is both indispensable and atypical. Both in terms of his ideas, and in his willingness to ask questions, Rav Kook embodied this commitment and courage, and can serve as a role model for Orthodox Jews today. For that reason, I was honored to speak with Professor Marc Shapiro, author of the new book , to learn more about Rav Kook’s ideas, and their application to the Orthodox world today. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Inside the Real Rules of War: Colonel John Spencer vs. Media Myths About Israel and Hamas (246)
04/28/2025
Inside the Real Rules of War: Colonel John Spencer vs. Media Myths About Israel and Hamas (246)
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 Israel faces on the battlefield, and what the world gets wrong about the rules of war. We also discuss whether Israel is succeeding in its stated goals, and how the war can conclude without turning into an endless quagmire. No matter your stage of life, Nishmat's Summer Beit Midrash is the place for you. This program offers transformative Torah learning for women of all backgrounds, in the heart of Jerusalem. Visit to learn more. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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OTD, Datlash, and the Religious Spectrum: When Orthodox Jews Leave Orthodoxy with Rabbi Alex Israel (CLASSIC EPISODE)
04/21/2025
OTD, Datlash, and the Religious Spectrum: When Orthodox Jews Leave Orthodoxy with Rabbi Alex Israel (CLASSIC EPISODE)
The 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. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Celebrating Pesach in Challenging Times: Haggadah Insights from Eight Teachers of Torah (245)
04/07/2025
Celebrating Pesach in Challenging Times: Haggadah Insights from Eight Teachers of Torah (245)
I’m doing something a little different this week. Instead of discussing an issue in the Jewish world, I want to offer some inspirational words about the Seder as we enter the final week before the beginning of Pesach. To that end, I invited several of my podcast guests from the past year to present ideas that they find meaningful, with the hope that they will enhance your own Seder as we navigate celebrating Pesach during this challenging moment in Jewish history. In this episode, you will hear divrei Torah from Dr. Yosefa Fogel Wruble, Olivia Friedman, Rabbi Yitzchak Shurin, Rabbi Dr. Judah Goldberg, Rabbi Ben Kelsen, David Bloom, Rabbi Dr. Rafi Zarum, and Rabbi Chayim Soloveichik. You can look in the show notes that accompany this podcast to see the time signatures for each dvar Torah. I hope and expect that their words of Torah and encouragement will resonate with you, and that they will give you additional ideas to think about as we prepare for the Pesach Seder this year. Timestamps for the divrei Torah: 2:06 - Rav Kook on internal freedom (Dr. Yosefa Fogel Wruble) 4:49 - Israel as God's first born child (Dr. Yosefa Fogel Wruble) 11:12 - Ha Lachma Ana (Olivia Friedman) 19:37 - Starting with disparagement and ending with praise (Rabbi Yitzchak Shurin) 28:11 - V'hi She'amda (Rabbi Dr. Judah Goldberg) 38:12 - The Ten Plagues (Rabbi Benjamin Kelsen) 55:13 - Dayeinu (David Bloom) 1:00:24 - Pesach, Matzah, u'Maror (Rabbi Dr. Raphael Zarum) 107:23 - Miyagon l'simcha (Rabbi Chayim Soloveichik) This week's episode is sponsored by Jewish Communal Fund, where strategic philanthropy meets impact. Visit to request an information kit. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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"There Are No Shortcuts to a Healthy Jewish Education": Empowering Growth Without Guilt or Fear, with Rabbi Dr. Judah and Rabbanit Shayna Goldberg (244)
03/31/2025
"There Are No Shortcuts to a Healthy Jewish Education": Empowering Growth Without Guilt or Fear, with Rabbi Dr. Judah and Rabbanit Shayna Goldberg (244)
We are now less than two weeks away from the night of the Seder, which is almost certainly the most widely practiced example of Jewish education in action. And that raises the issue of how we should define healthy Jewish education in general, and how best we can achieve it. These questions are doubly important because while there are many wonderful Jewish schools, there are, unfortunately, numerous educational institutions where religious growth and educational goals are met through the use of fear, guilt, charismatic authority, manipulation, and condescension. Whether or not it “works” is irrelevant; education that relies on unhealthy approaches is damaging, unfair, and destructive. This episode with Rabbi Dr. Judah and Rabbanit Shayna Goldberg, explores fresh, student-centered approaches to Jewish learning that prioritize autonomy, personal meaning, and emotional well-being. We challenge guilt- and fear-based models, advocating for an education that nurtures curiosity and critical thinking, while emphasizing lifelong love of Torah, Jewish law, and Jewish tradition. How can we empower our children and students to take ownership of their learning while staying rooted in the values we want to impart? How do we create environments where kids feel both supported and free to make their own choices? We examine how Jewish education can inspire, uplift, and cultivate independent, engaged learners who embrace Torah Judaism without losing their sense of self. This week's episode is sponsored by Jewish Communal Fund, where strategic philanthropy meets impact. Visit to request an information kit. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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A Moral Voice for Religious Zionism: The Profound (and Profoundly Human) Thought of Rav Yehuda Amital, with Rabbi Moshe Taragin (243)
03/24/2025
A Moral Voice for Religious Zionism: The Profound (and Profoundly Human) Thought of Rav Yehuda Amital, with Rabbi Moshe Taragin (243)
This conversation with Rabbi Moshe Taragin presents an introduction to the profound - and profoundly human - religious philosophy of Rav Yehuda Amital zt'l, the founding rosh yeshiva of Yeshivat Har Etzion. Rav Amital's ideas fill a unique niche in the Religious Zionist world today, and in many ways stand as a corrective to some of the ideology that has become dominant in the dati leumi world. His teachings grapple with some of the most pressing tensions in Jewish thought and life: universalism vs. particularism, the relationship between morality and halacha, and the relevance of Tanach as a guide to contemporary events. In this engaging discussion, Rabbi Taragin and I explore Rav Amital's vision of faith, statehood, and leadership, as well as his emphasis on joy and serenity in religious service. Rabbi Amital’s unique perspective on Zionism, ethics, and spirituality continues to inspire and challenge, offering guidance for those seeking a thoughtful and compassionate approach to Judaism and the modern world. Perhaps more than ever before, we need to hear his voice loudly and clearly so that Religious Zionism can represent the positive and diverse force that it can be, rather than the sometimes narrow and shallow force that, at times, it is in danger of becoming. Tune in as we uncover the depth and relevance of Rabbi Amital’s ideas, bringing his legacy to life for today’s listeners. This week's episode is sponsored by Jewish Communal Fund, where strategic philanthropy meets impact. Visit to request an information kit. To purchase Rabbi Taragin's new book, To Be Holy but Human: Reflections Upon My Rebbe, HaRav Yehuda Amital, click Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Chutzpah - and Illegal Activity - in the Service of Dodging the Draft, with Sam Sokol (242)
03/17/2025
Chutzpah - and Illegal Activity - in the Service of Dodging the Draft, with Sam Sokol (242)
When hundreds of students enthusiastically sing and dance about dodging the draft, while thousands of others protect those same students by spending more and more time in the IDF because of a manpower shortage... something has gone seriously wrong. When institutions that receive millions of shekels of government money actively undermine the State of Israel by encouraging and celebrating draft dodging... something has gone seriously wrong. When a minister in the Knesset is involved in creating a hotline that is used to tell people who have received draft notices to ignore them entirely... something has gone seriously wrong. In this episode, I spoke to Sam Sokol to learn more about the Chareidi political echelon's attempts to enshrine military exemptions into law, and how in the meantime, some Chareidi institutions are literally committing felonies in the service of discouraging military service. There is a lesson for all of us in this, too. As I assert at the end of the episode: if you are absolutely convinced of the rightness of your ideology such that you won’t listen to anyone else, and when that ideology effectively becomes the most important thing in the world, not only does it become a type of idolatry, but it also can potentially lead you to actions that are immoral, unethical, and illegal. And when you have no respect for the institutions that support you, and engage with them only in order to get from them without any expectation of giving anything back, you may end up doing actions that are immoral, unethical, and illegal. In my opinion, this is a tragedy embodied by some leaders in the Chareidi world. This week's episode is sponsored by Jewish Communal Fund, where strategic philanthropy meets impact. Visit to request an information kit. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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The Mainstreaming of Meir Kahane: A Halachic, Moral, and Theological Mistake, with Rabbi Dr. Tzvi Sinensky (241)
03/10/2025
The Mainstreaming of Meir Kahane: A Halachic, Moral, and Theological Mistake, with Rabbi Dr. Tzvi Sinensky (241)
Several recent articles have raised a troubling question: Is Rabbi Meir Kahane making a comeback? In the wake of the horrific murder of Shiri, Ariel, and Kfir Bibas, some influential pro-Israel voices have turned to Kahane’s ideas, reviving a debate that many thought was long settled. In this episode, Rabbi Dr. Tzvi Sinensky and I dive deep into why this is a dangerous trend—one that must be confronted head-on from a Torah perspective. While many may be invoking Kahane’s philosophy with Israel’s best interests at heart, we argue that his ideas are fundamentally flawed—halachically, morally, and philosophically. We’ll explore why it’s crucial to openly discuss why Kahanism should not be part of the Jewish discourse, and why those who cite him must rethink their position before it spreads any further. Tune in to understand why the resurgence of Kahanist thought in certain circles is a threat to the very values we hold dear—and why we must stop it before it gains more traction. This week's episode is sponsored by Jewish Communal Fund, where strategic philanthropy meets impact. Visit to request an information kit. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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The Abuser’s Tool Box: Domestic Abuse in the Orthodox Community, with Keshet Starr (240)
03/03/2025
The Abuser’s Tool Box: Domestic Abuse in the Orthodox Community, with Keshet Starr (240)
Domestic abuse is one of those topics that, sometimes, we simply wish would go away. It’s certainly among the very worst experiences that a person can have, yet it brings forward feelings of shame and failure, such that people are often reluctant to acknowledge that they are victims. Sometimes, they can’t even name it - either because they don’t recognize it for what it is, or because they are embarrassed and don’t want to admit it. Yet we can’t ignore it, and all of us need to better recognize the warning signs and the red flags - both for those inside and outside of a relationship - and, should such warning signs exist, what we can potentially do about it. Because this is such an important (albeit disturbing) topic, I was honored to speak to Keshet Starr, the CEO of Shalom Task Force, to learn more. We talked about the distinction between domestic abuse and domestic violence, the prevalence of male to female abuse versus female to male abuse, examples of non-violent abusive behavior (“the abuser’s tool box”), how can we determine when normal behavior crosses the line into emotional abuse or controlling behavior, the range and spectrum of inappropriate controlling behavior, whether the typical abuser is conscious of being an abuser, the way that an abuser often thinks of himself as “owning” his spouse, answering claims that domestic violence does not occur in Orthodox homes, how abuse takes place in ways that we cannot visibly see, the use of Jewish texts and religious ideas to justify abuse and break boundaries, warning signs and red flags, whether abuse should lead to divorce or if can it potentially be worked on (and why professionals won’t offer an opinion on that question), education against abuse, the meaning of spiritual abuse, barriers to getting help, and more. To reach the Shalom Task Force’s confidential hotline, go to . Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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The Vanishing Art of Jewish Conversation (and What To Do About It), with Dr. Yosefa Fogel Wruble (239)
02/24/2025
The Vanishing Art of Jewish Conversation (and What To Do About It), with Dr. Yosefa Fogel Wruble (239)
The act of talking - dignified and informative conversation, where people connect on a serious level with one another - is essential to the Jewish experience. This goes back to the very creation of Adam; the Torah describes God as breathing a breath of life into Adam, after which he became a nefesh chaya - a living soul. Targum Onkelos famously translates that phrase as ruach memalela - a speaking spirit. Accordingly, the fact that man is able to converse is part of his very essence. In a similar way, the Torah is composed of not only written words, but also the Torah Sheba’al Peh - the conversation that began with Moshe Rabbeinu and has continued through the ages until today. It’s not an understatement to suggest that conversation is part of the lifeblood of Judaism. Nevertheless, it sometimes seems that the art of conversation, like so many other aspects of 21st century culture, is changing in ways both good and bad. For example, the explosion of the popularity of podcasts demonstrates that people still crave stimulating conversation - but on the other hand, the people listening in are not active participants and don’t add to the discussion. In many ways, it seems that deep conversations between people are overridden by the myriad distractions that keep us glued to our phones and less present when someone wants to have our full attention. In a lot of ways, conversation has, at times, become vacuous - with potentially devastating consequences for interpersonal relationships. So this episode of the podcast will be a conversation about conversations, and I was honored to speak to Dr. Yosefa Fogel Wruble to discuss a wide variety of topics related to authentic dialogue. I really got a lot out of this conversation, and it was actually quite different from many other episodes of this podcast. We dealt with many issues, from the Rambam’s ideas about speech, what we learn from sitting shiva, and the changing nature of teaching Torah, to phone notifications and Spotify playlists and the Red Sox and why we each got into the world of podcasting. It was a lot of fun, it was very informative, and I think you’ll enjoy listening in as much as I enjoyed participating. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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Religious Jews and Dishonesty: Tax Fraud, Zoning Violations, Downplaying Risk, and More, with Rabbi Jeremy Wieder (238)
02/17/2025
Religious Jews and Dishonesty: Tax Fraud, Zoning Violations, Downplaying Risk, and More, with Rabbi Jeremy Wieder (238)
The Torah is very clear that theft is forbidden; no one doubts that this is true. It is, accordingly, very disturbing that religious Jews as a community don’t seem to be more ethical in these matters than people who don’t see the Torah as their guide to life. I am not suggesting that Orthodox Jews are worse than anyone else in these matters; I cannot possibly know if that’s true. It does seem, however, that Orthodox Jews as a whole are not better than any other community when it comes to honesty in business and taxes. We have heard of too many religious people who find themselves in serious legal trouble to pretend that our community actually maintains a higher ethical standard. The fact that people who learn Torah and daven with a minyan - people who are careful about Shabbat, kashrut, and taharat hamishpacha - are sometimes not nearly as careful when it comes to business law, is an embarrassment that we need to rectify. As Torah Jews, we need to be better - and for that reason, I was honored to speak to Rabbi Jeremy Wieder about some commonly disregarded halachot, including tax evasion, paying a worker in cash so he can presumably avoid paying taxes, building in violation of zoning laws without getting permission from the city, the definition of “ona’ah” - overcharging - in a market economy, pyramid schemes, downplaying risk when trying to convince someone to invest money, not declaring merchandise bought outside of Israel when entering the country, and more. We also talked about why in these matters, integrity may require going further than the letter of the law, and a possible reason that people who study Torah may try to justify that which is obviously unacceptable. Finally, we talked about the problem of religious Jews ignoring the crimes of people who give extensively to charity, or even sometimes lionizing them for their faith in God when they were in prison - while conveniently ignoring the reasons that they went to prison in the first place, or pretending that they were victims, or committed “victimless” crimes, when, in fact, this is false. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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The Ethics of Population Transfers & Prisoner Swaps, Defining "Innocent Civilians," and Other Urgent Ethical Dilemmas, with Rabbi Dr. Shlomo Brody (237)
02/10/2025
The Ethics of Population Transfers & Prisoner Swaps, Defining "Innocent Civilians," and Other Urgent Ethical Dilemmas, with Rabbi Dr. Shlomo Brody (237)
Ever since President Trump presented his plan (or his idea, as it’s unclear how planned out this really is) about resettling the Arab population of Gaza, the Jewish world has been in an uproar. Very loud voices on both sides of the issue have been talking not so much about its feasibility - many are extremely skeptical that this could ever come to fruition - but about whether it is ethical. Some insist that this is nothing less than ethnic cleansing, with all the negative implications that the term contains, while others suggest that this is completely different, and that if starting a war of aggression has no long-term negative consequences for the aggressor, then nothing will ever act as an effective deterrent to further attempts at genocide of the Jewish people. This is only one of the ethical issues that has arisen in the weeks since the ceasefire, and I was honored to speak with Rabbi Dr. Shlomo Brody to hash out some of the major ethical and moral dilemmas presented by the current situation. Along with the question of population transfer, Rabbi Brody and I also talked about leadership and the ethics of taking responsibility, the moral question of toppling a government during wartime, the propriety of exchanging Palestinian prisoners - many of whom have blood on their hands - for Israeli hostages, when it is right to start a war rather than to use diplomacy, how we can define victory in war, how we determine the innocence of civilians who support a terrorist government even if they don’t participate in its atrocities directly, and much more. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to . Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (). Thanks to all of our Patreon subscribers, who have access to bonus JCH podcasts, merch, and more - we appreciate your help, and hope you really enjoy the extras! Visit the JCH Patreon site at . Check out for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com
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