

Orthodox Conundrum
Scott Kahn
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.
Episodes
Mentioned books

Feb 2, 2026 • 1h 30min
When We Get It Wrong: Orthodox Communities and the Nechemya Weberman Case (279)
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 early access and additional bonus content! This episode of Orthodox Conundrum addresses an extremely painful and unsettling subject. Last week, we learned that Nechemya Weberman, who was convicted of repeatedly sexually abusing a minor, has had his prison sentence dramatically reduced. Although Weberman originally received a sentence of more than one hundred years, that sentence has now been cut to eighteen years, making him eligible for release in about two years. For many people, this news was shocking. For others, it felt like a confirmation of something they have feared for a long time. Because this is not only a legal story. It is a communal one. It forces us to ask not only what the court decided, but what happens when justice intersects with communal loyalty, religious authority, and the instinct to protect our own. This conversation is not about whether a crime occurred. That question was answered years ago in a court of law. The deeper question is what happens afterward. How communities respond. Whose voices are believed. And whose pain is ignored or exacerbated - sometimes consciously and openly - so that communal stability can be preserved. To help explore those questions, I am joined by three people who bring deeply informed and very different perspectives. Asher Lowy of Za'akah has followed the Weberman case for more than a decade and understands its history and its communal aftermath in ways few others do. Sarena Townsend is the attorney who represented the victim and worked to oppose the reduction of Weberman's sentence. And Shana Aaronson, the head of Magen in Israel, brings the essential perspective of victim safety, trauma, and what these decisions mean for survivors long after court proceedings end. Together, we discuss how and why the sentence was reduced, what remorse and rehabilitation are supposed to mean, and why in this case those concepts ring hollow for so many. But we also confront something even more uncomfortable. What does it say about a religious community when protection is extended more readily to perpetrators than to victims? And what happens when our drive to preserve our institutions and community structures leads us to abandon our internal moral compass? This is not an easy conversation. But it is one we cannot afford to avoid. To listen to the latest Q&A episode of Intimate Judaism, click here. Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108). 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 https://www.patreon.com/jewishcoffeehouse. Write to aliza@jewishcoffeehouse.com to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com

Jan 26, 2026 • 1h 16min
No Rewind Button: Why "It Never Happened Before" Isn't Enough, with Rabbi Yakov Horowitz and Rabbanit Dr. Yardaena Osband (278)
Rabbanit Dr. Yardena Osband, pediatrician and Torah educator, and Rabbi Yaakov Horowitz, child-safety advocate and educator, discuss community safety and prevention. They explore why longevity does not equal safety. They examine faith versus responsibility, cognitive denial in communities, vaccine trust, practical safety measures, and how leaders can model and enforce protective norms.

12 snips
Jan 19, 2026 • 1h
Does the Torah Demand Independent Thought? Rabbi Aryeh Klapper on Gedolim, Authority and Halacha (277)
Rabbi Aryeh Klapper, Dean of the Center for Modern Torah Leadership, delves into the tension between authority and independent thought in religious life. He argues that kavod, or respect, should be voluntary and warns against enforced reverence that undermines personal responsibility. Klapper explores the 'gedolim' as a political construct, challenges blind adherence to authority, and emphasizes the importance of individual moral accountability. He also discusses the necessary balance of communal decisions and personal judgment in navigating halachic authority.

Jan 12, 2026 • 1h 30min
The Dating Process: An Honest Conversation for Those Dating and Their Parents, with Rabbanit Shayna Goldberg (276)
Rabbanit Shayna Goldberg, a veteran educator and author, dives deep into the complexities of dating and decision-making. She emphasizes the importance of trust and respect as the foundations for healthy relationships. Through personal anecdotes and insightful advice, she encourages singles to distinguish between non-negotiables and preferences while dating. Shayna also explores how strong chemistry can overshadow long-term compatibility and provides strategies to break decision paralysis, urging listeners to focus on manageable 'next decisions' and the power of intuition.

Jan 5, 2026 • 59min
Turning Criminals Into Heroes: Rabbi Jeremy Wieder on Rubashkin, Pollard, and Moral Clarity (275)
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 even served jail time, and we nevertheless elevate them to the status of heroes - not necessarily despite their criminal behavior, but in some ways almost because of it. Just a couple of weeks ago, Mishpacha magazine ran a glowing feature calling Sholom Rubashkin "the emunah and bitachon rebbe of the entire Jewish world," as though the only relevant fact of his story is his early release from prison. But as the record makes clear, including extensive evidence presented at trial, Rubashkin was involved in significant fraud, money laundering, and the exploitation of undocumented workers. Was his sentence excessive and unfair? Absolutely. Was there government overreach? No question. But that's not the same thing as innocence, and certainly not a basis for turning someone into a moral authority. Let me be clear: many of us have done things that we're not proud of, and that we wish we had done differently. The fact that Rubashkin went to jail is not the issue, so much as the fact that despite the real evidence, much of the Orthodox world treats him as if he were an innocent man who did nothing wrong, rather than an example of someone who was both perpetrator and victim. If he presented himself as an example of a baal teshuva, I would have no complaint. I would be pleased and fully supportive if we looked at him as someone who committed crimes, but has repented and is now living an honest life. And if he acknowledged his conviction as just and also complained about government overreach, he would be in the right. But that's not what's happening - and the consequences for the Orthodox self-image and behavior are serious. And this is not just a Haredi phenomenon. In the Modern Orthodox world, Jonathan Pollard has long been held up as a heroic defender of Israel. But as Rabbi Jeremy Wieder points out in our conversation, Pollard betrayed the country of which he was a citizen, took large sums of money for his actions, and passed along intelligence, the scope of which none of us fully know. The fact that the U.S. government mishandled his sentencing - which is terrible - does not magically transform espionage into idealism. So why do we do this? Why does our community repeatedly turn criminals into role models—sometimes even into teachers of faith and morality? What psychological, sociological, and ideological needs are we trying to satisfy? And more importantly: what message are we sending to our children when we confuse suffering with righteousness, and denial with integrity? In today's episode, Rabbi Jeremy Wieder helps us unpack all of this. We discuss Rubashkin, Pollard, Aryeh Deri, the role of media and influencers, the dangers of denial and victimhood narratives, and the guardrails communities should adopt so that real role models—not the loudest, or the most dramatic, or the most persecuted—become the people we admire. It's an honest and necessary conversation about integrity, responsibility, and choosing heroes who actually reflect Torah values. 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. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108). 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 https://www.patreon.com/jewishcoffeehouse. Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com

Dec 29, 2025 • 1h 25min
A Person is a Subject, not an Object: New Traditional Perspectives on Tzniut, with Bracha Poliakoff and Rabbi Anthony Manning (CLASSIC EPISODE)
In this insightful discussion, Bracha Poliakoff, a licensed clinical social worker and writer, and Rabbi Anthony Manning, a seasoned educator, explore the concept of tzniut, or modesty. They redefine tzniut beyond mere clothing, emphasizing dignity and self-respect for all genders. The guests tackle the negative connotations and trauma associated with tzniut education, the harmful weaponization of modesty, and the importance of community standards. They advocate for a balanced, respectful approach to halachic teaching and highlight the need for a more inclusive understanding of tzniut.

Dec 23, 2025 • 1h 10min
When Non-Jews Define Judaism for Jews: Alyza Lewin on Reclaiming Jewish Peoplehood in an Age of Intimidation (274)
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 vilification of Israel is the vilification and targeting of Jews as a people, on the basis of peoplehood, ancestral heritage, and our connection to the Land of Israel - even though those who do so may not publicly acknowledge that this is their philosophy of Judaism. And that itself is part of the problem: people who are not Jewish who think that they can decide the definition of Judaism and Jewishness. This is a process that is happening now, but its antisemitic roots go back 800 years. That is part of why the chants and the intimidation land the way they do, and why the world's inability to even recognize the nature of the attack has left so many Jews feeling isolated. Strangely enough, Alyza argues that despite the pain, there is a silver lining: namely, the reinvigoration of Jewish identity, and faith in God, among many of those who, until October 7th, gave very little thought to their Jewish heritage. So in this conversation, we address a series of very practical questions, rather than dealing with antisemitism in the abstract. We ask how, in a society with broad legal protections for free speech, we should deal with the huge grey zone where speech has consequences the law may not address. How do we distinguish good faith political debate from the vilification of Jews, especially when universities watched this for years and still misread it as a normal dialogue? What should Jewish students do when activists demand that they shed Jewish peoplehood and connection to Israel in order to be accepted, and why does Alyza insist the answer is not to take the bait, but to say clearly: you have no right to tell me what it means to be Jewish? Should we retire the term Zionism, or reclaim it? And crucially, we also tackle one of the most emotionally charged pairings in today's discourse: antisemitism and Islamophobia, and how that framing often shapes, and sometimes distorts, the conversation in the public square. Ultimately, we are dealing with reinvigoration of Jewish peoplehood. Because if we do not name Jewish peoplehood clearly, we will keep losing the argument before it even begins. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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. (Join here.) No question is off limits, and all submissions will remain anonymous. We're looking forward to answering your questions on our first episode! Please listen to and share this podcast, and let us know what you think on the Orthodox Conundrum Discussion Group on Facebook (https://www.facebook.com/groups/432020081498108). 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 https://www.patreon.com/jewishcoffeehouse. Check out https://jewishcoffeehouse.com/ for the Orthodox Conundrum and other great podcasts, and remember to subscribe to them on your favorite podcast provider. Also visit https://www.jchpodcasts.com/ to learn all about creating your own podcast. Music: "Happy Rock" by bensound.com

Dec 15, 2025 • 1h 18min
Jewish Particularism or Cultural Engagement: A Chanukah Debate, with Rabbi Yitzchok Adlerstein and Rabbi Dr. Raphael Zarum (273)
Rabbi Dr. Raphael Zarum, Dean of the London School of Jewish Studies, and Rabbi Yitzchok Adlerstein, Director of Global Faith Engagement for Israel365, explore the tension between Jewish particularism and cultural engagement. They debate how Chanukah embodies this struggle, with Adlerstein advocating for a focus on Jewish distinctiveness, while Zarum emphasizes the importance of engagement and selective assimilation. They also discuss the impact of modern culture on Jewish values, the role of literature and media in shaping beliefs, and the need for discernment in cultural interactions.

10 snips
Dec 8, 2025 • 1h 22min
A $10,000 Bottle of Scotch: Alcohol Abuse, Conspicuous Consumption, and Orthodox Life Today, with Rabbi Jonathan Muskat and Rachel Tuchman (272)
Rabbi Jonathan Muskat, an Orthodox leader in Jewish education, and Rachel Tuchman, a licensed mental health counselor, tackle the concerning normalization of alcohol use within Orthodox communities. They discuss how 'mommy wine' culture and social media pressure contribute to problem drinking among families. The duo explores the implications of luxury consumption on values and community dynamics. They emphasize the need for healthier family practices and rituals to promote genuine happiness over materialism, urging parents to model mindful consumption.

Dec 1, 2025 • 1h 24min
Chosen Vs. Unchosen Vs. Rejected: The Idea of a Chosen People in an Antisemitic World, with Rabbanit Yael Leibowitz (271)
Yael Leibowitz, an Israeli educator and Tanakh scholar, dives into the complexities of the concept of chosenness amidst rising antisemitism. She explores Biblical narratives, from Cain and Abel to the Tower of Babel, to reveal how these stories inform Jewish identity and responsibility. Yael argues that chosenness is about role rather than superiority, emphasizing the need for differentiation and the dangers of cultural homogeneity. She also addresses how Tanakh can offer guiding principles for contemporary challenges while cautioning against misinterpretation for modern policies.


