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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

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All Episodes

59:28

Turning Criminals Into Heroes: Rabbi Jeremy Wieder on...

Orthodox Conundrum ·

2026/01/05

Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/ - and paid subscribers get this and other episodes of the Orthodox Conundrum Podcast ad-free and with additional bonus content! There's a recurring pattern in parts of the Orthodox world - one that has always troubled me, but in recent years has become impossible to ignore. We take individuals who have committed serious wrongdoing, sometimes admitted it in court, sometimes

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01:25:27

A Person is a Subject, not an Object: New Traditional...

Orthodox Conundrum ·

2025/12/29

Enjoy this classic episode from May, 2023. We'll be back next week with a brand new episode. Tzniut is triggering. That became clear when the Orthodox Conundrum Podcast released episode 145 entitled, "The Challenges of Teaching Tzniut & the Challenges of Being Tzanua, with Shayna Goldberg." That episode, in which Scott asked Shayna to focus on issues related to tzniut (modesty) and clothing, addressed some of the most pressing concerns, and the conversation generated quite a bit of discussion

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01:10:20

When Non-Jews Define Judaism for Jews: Alyza Lewin on...

Orthodox Conundrum ·

2025/12/23

There is a fundamental mistake that many people still make about Jews: they see Judaism exclusively as a faith, so they assume Jewish needs are basically religious accommodations, kosher food, holiday absences, maybe a space to pray. But my guest today, attorney Alyza Lewin, argues that if that's your starting point, you completely misunderstand the nature of Judaism, and what Jews are experiencing across the world. Because what we are watching on campuses, on Bondi Beach, and in the international

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01:17:43

Jewish Particularism or Cultural Engagement: A...

Orthodox Conundrum ·

2025/12/15

To what degree should we assimilate non Jewish thought and culture into our intellectual, emotional, and spiritual lives? And to what degree does that question affect the way that we celebrate Chanukah? Rav Shimshon Raphael Hirsch expressed this tension directly when he wrote the following words: Chanukah represents the clash of two doctrines, two views, two civilizations, capable of molding opinions, training and educating those who until this very day compete for the mastery of the world

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01:22:04

A $10,000 Bottle of Scotch: Alcohol Abuse,...

Orthodox Conundrum ·

2025/12/08

A tragic drunk driving case in Lakewood has pushed an uncomfortable question to the surface. What happens when "Toameha," kiddush clubs and casual drinking culture quietly normalize alcohol misuse in our homes and shuls, especially for the teenagers who are watching us... and what happens when that same culture is surrounded by designer logos, luxury Shabbat tables and endless talk about hotels and vacations? In this episode, I speak with Rabbi Jonathan Muskat and mental health counselor Rachel

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01:23:37

Chosen Vs. Unchosen Vs. Rejected: The Idea of a...

Orthodox Conundrum ·

2025/12/01

In the past two years many Jews have felt as if the world they thought they knew simply disappeared. Western democracies, universities, and social justice spaces that once seemed welcoming - or at least somewhat neutral - have turned openly hostile toward Israel and the Jewish people. At the center of much of this hatred is a familiar accusation: that Jews think they are chosen, and accordingly, Jews think they are better. While we wholeheartedly reject the antisemitism implicit in this assertion,

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01:44:26

Painful Questions and Unconditional Love: Orthodox...

Orthodox Conundrum ·

2025/11/24

Back in August, I released a conversation with Rabbi Yakov Horowitz about Orthodox parents whose children come out as LGBTQ. The feedback to that episode was intense. Some listeners wrote that they finally felt seen. Others said that they were deeply uncomfortable. Quite a few parents asked what they should actually do when their son or daughter comes out to them, and how they can respond with genuine love while remaining faithful to halacha. Those questions are not theoretical. They are deeply

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01:09:06

Hostility, Confusion, and Ideological Pressure:...

Orthodox Conundrum ·

2025/11/17

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

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01:13:45

Mamdani, Fuentes, Tucker, and Mainstreaming...

Orthodox Conundrum ·

2025/11/10

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

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01:07:09

Charedi, Dati Leumi, Modern Orthodox, Traditional,...

Orthodox Conundrum ·

2025/11/03

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

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01:03:07

The World is a Beautiful Place... and We Need to Earn...

Orthodox Conundrum ·

2025/10/27

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

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01:13:00

Seven Facets of Healing: Rabbi Leo Dee’s Blueprint...

Orthodox Conundrum ·

2025/10/20

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)..

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01:05:38

Eulogies and Boundaries: Orthodox Jews and the Legacy...

Orthodox Conundrum ·

2025/09/30

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

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01:15:41

God's Loyal Opposition: Anger, Faith, and Divine...

Orthodox Conundrum ·

2025/09/15

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

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01:12:21

Suppressed, Rediscovered, Essential: Rav Kook’s Lost...

Orthodox Conundrum ·

2025/09/08

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

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58:13

Learning Tanach Daily Through 929: Opportunities,...

Orthodox Conundrum ·

2025/09/01

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

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01:06:58

Orthodox Parents and Their LGBTQ Children, with Rabbi...

Orthodox Conundrum ·

2025/08/24

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,

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01:04:23

When Mitzvot Lose Their Meaning: Rabbi David Stav on...

Orthodox Conundrum ·

2025/08/18

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

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57:10

The Bible, the Beasts, and the Big Lies About Israel,...

Orthodox Conundrum ·

2025/08/11

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

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01:08:29

Disagreeing Like Moses: A Torah Blueprint for...

Orthodox Conundrum ·

2025/07/28

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

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305 results

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