Religious Jews and Dishonesty: Tax Fraud, Zoning Violations, Downplaying Risk, and More, with Rabbi Jeremy Wieder (238)
Release Date: 02/17/2025
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...
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When Mitzvot Lose Their Meaning: Rabbi David Stav on Reconnecting Orthodox Youth to Jewish Law (259)
Orthodox Conundrum
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...
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The Bible, the Beasts, and the Big Lies About Israel, with Rabbi Dr. Natan Slifkin (258)
Orthodox Conundrum
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....
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Disagreeing Like Moses: A Torah Blueprint for Conflict Resolution (257)
Orthodox Conundrum
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...
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Must Every Jew Be Shomer Shabbat? A Fresh Perspective on Kiruv, with Rabbi Simi Lerner (256)
Orthodox Conundrum
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...
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Overeating, Obesity, Ozempic, and Orthodox Jews, with Dr. Sharon Grossman (255)
Orthodox Conundrum
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...
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Will Charedi Society Face Reality? Dayan Yehoshua Pfeffer on Work, Faith, and the Future of the Torah Community (254)
Orthodox Conundrum
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...
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Faith, Prayer, and the Impossible: Rabbi Shlomo Brody on Emunah, Miracles, Reality, and the Power of Tefillah (253)
Orthodox Conundrum
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,...
info_outlineThe 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.
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