Orthodox Conundrum

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

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.

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

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.

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.

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.

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 personal, and they are coming from people who keep Shabbat, send their kids to day schools, sit in our shuls, and are trying to raise their families as loyal Torah Jews. Ignoring them does not make them go away. Today I am speaking with two people who have decided not to look away. Rabbi Menachem Penner is the former dean of RIETS and currently serves as the executive vice president of the Rabbinical Council of America. Together with his wife Adeena he founded Kesher Families, an organization that supports Orthodox parents of LGBTQ children. Rabbi Yakov Horowitz is the founder of Project YES and a co leader of Kesher Families, and he joined me for that earlier conversation. In this episode we talk about what moved the Penners to start Kesher Families, what it was like for Rabbi Penner to be a very public rabbinic figure when his son came out, and why they chose to share their family story with the broader community. We discuss the first things a parent should and should not say when a child comes out, the confusion that many young people feel as they try to understand their own sexual identity, and how parents can balance acceptance of what a child is telling them with the awareness that some parts of the story may still be unfolding. We also look at how attitudes in the Orthodox world have changed over the past decade, what has improved, what remains painful, and whether it is really possible to increase compassion and understanding without abandoning our mesorah. And finally, I ask both of my guests what single message they most want the Orthodox community to hear about LGBTQ children and their families. To learn more about all that Dreamearly does, go to https://dreamearly.co/. Make sure to check out the excellent recent episode of the Stream of Dreamearly Podcast with Dr. David Rosmarin. To contact Kesher Families, click here. Follow Rabbi Yakov Horowitz on Instagram - @yakovhorowitz and @brightbeginningsforum. 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

Rabbi Mark Wildes, founder of Manhattan Jewish Experience and expert on Jewish outreach, discusses the impact of New York's mayoral election on Jewish safety and identity. He tackles the troubling connection between anti-Zionism and antisemitism, emphasizing that understanding this distinction is essential. Wildes shares insights on engaging politically left-leaning young Jews and highlights the importance of teaching religious Zionism in outreach efforts. He also provides practical steps for Jews feeling disenfranchised, advocating for Shabbat practice and studying Torah.

In recent weeks we have watched something many of us hoped we would not see in the United States: openly anti-Zionist and even openly antisemitic voices moving from the margins into the mainstream. Zohran Mamdani's victory in New York raises the chilling possibility that hostility to Israel is now an electoral asset. At the same time, parts of the American right are flirting with figures like Nick Fuentes, a Holocaust denier who says Jews do not belong in Western civilization. To make sense of this moment, I spoke with Jonathan Greenblatt, CEO and National Director of the Anti Defamation League. We discussed why anti-Zionism is, in most cases, antisemitism; what Mamdani's rise should signal to American Jews; why some university leaders defend the indefensible; where the Jewish community itself has made mistakes in fighting antisemitism; how to confront hatred coming from both sides of the political spectrum without turning it into a partisan game; and more. This is a blunt, timely, and deeply important conversation for anyone who cares about Jewish security and moral clarity in public life. 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

Is Jewish unity even possible? In this urgent episode Rav Yosef Zvi Rimon faces the hardest questions raised by the draft crisis and by the widening gaps between Charedi, Dati Leumi, Modern Orthodox, Traditional, and Secular Jews. He explains why unity is not a slogan but a practical necessity and religious obligation with real consequences for security, community, and our shared future. With clarity and empathy he maps a path for principled disagreement, mutual responsibility, and practical steps that families, shuls, and schools can take right now. If you are tired of talking points and want a serious plan for healing rifts while staying true to conviction, this conversation is for you. 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