Orthodox Conundrum

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 https://scottkahn.substack.com/. 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  

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 Renewing the Old, Sanctifying the New: The Unique Vision of Rav Kook, 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 https://scottkahn.substack.com/. 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

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 nishmat.net/summer-beit-midrash to learn more. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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

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 https://scottkahn.substack.com/. 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

Join esteemed guests like Rabbi Benjamin Kelsen, who delves into the Makot and their comforting relevance during the Pesach Seder. Rabbi Dr. Judah Goldberg highlights Pesach as the holiday of Brit Avot, celebrating the ongoing covenant with God. Dr. Yosefa Fogel Wruble shares Rav Kook's insights on internal freedom and Israel's unique role. Rabbi Yitzchak Shurin explores the dual aspects of freedom in the Haggadah, and Olivia Friedman discusses themes of hunger and community. Rabbi Chayim Soloveichik reflects on the journey from agony to joy, offering profound messages for a transformative Seder.

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 https://jcfny.org/orthodoxconundrum/ to request an information kit. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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

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 https://jcfny.org/orthodoxconundrum/ 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 here. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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

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 https://jcfny.org/orthodoxconundrum/ to request an information kit. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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

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 https://jcfny.org/orthodoxconundrum/ to request an information kit. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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

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 https://shalomtaskforce.org/contact. Check out Orthodox Conundrum Commentary on Substack and get your free subscription by going to https://scottkahn.substack.com/. 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