Celebrating Pesach in Challenging Times: Haggadah Insights from Eight Teachers of Torah (245)
Release Date: 04/07/2025
Emergency Episode: The U.S. Attacks Iran — What It Means for Israel, Hamas, and the Future of the War (252)
Orthodox Conundrum
When the United States bombed Iran’s nuclear sites this week, the Middle East—and the world—entered a new phase of conflict. In this urgent episode, Scott speaks once again with Yaakov Katz, former editor of The Jerusalem Post, about what these strikes mean for Israel’s war effort, the potential consequences of regime change in Iran, the risks of escalation, and how this moment may redefine the geopolitical landscape. This is essential listening for anyone who wants to understand what’s really happening beyond the headlines. Check out the Tehillim Unveiled Podcast! Their episode on...
info_outline
The New Face of American Antisemitism: Violence, Politics, and Denial (BONUS EPISODE)
Orthodox Conundrum
Two Israeli embassy staffers shot in Washington. Jewish activists burned in Boulder. A mayoral candidate in New York who refused to condemn the Holocaust gaining momentum. Antisemitism in the United States is no longer hiding in the shadows — it’s on the march, in broad daylight. In this urgent bonus episode of Orthodox Conundrum, Scott Kahn speaks with Rabbi Chaim Steinmetz and Andy Weiss about the troubling rise in antisemitic violence and rhetoric, the mainstreaming of hate, and how American Jews are responding — with concern, activism, and a growing sense of alarm. From Zohran...
info_outline
Unscripted Reflections: Israel, Iran, and the Challenge of Faith in Wartime (251)
Orthodox Conundrum
In this spontaneous and unfiltered episode of Orthodox Conundrum, Scott shares heartfelt reflections on Israel’s war against Iran—not from a political or military perspective, but through personal experience and the lens of faith. What does it mean to believe in Divine providence during a time of fear and uncertainty? How should we grapple with the moral and spiritual implications of war? Without a script or agenda, this episode wrestles with the difficult questions that arise when religious conviction meets the harsh realities of conflict. Check out Orthodox Conundrum Commentary on...
info_outline
What Comes Next? Yaakov Katz on Israel’s War, Netanyahu’s Calculations, and the Search for an Endgame (250)
Orthodox Conundrum
Twenty months into the war with Hamas, many Israelis and supporters abroad are asking the same urgent question: how will this end? In this in-depth episode of Orthodox Conundrum, Scott Kahn is joined by Yaakov Katz, one of Israel’s most respected journalists and author of While Israel Slept, to examine whether Israel’s military goals are still realistic — or even defined. They discuss the uncertain state of the war, Netanyahu’s political maneuvering, the role of the Chareidi parties, international pressure, and the trust gap between the government and the public. It’s a sobering...
info_outline
From Beit Lechem to the Royal Ball: Comparing and Contrasting the Book of Ruth and Cinderella, with Rabbi Dr. Joshua Berman (249)
Orthodox Conundrum
Megilat Rut — the Book of Ruth — is one of the most beloved and widely read books in the Hebrew Bible. Because we read it annually on Shavuot, many people are familiar with its basic storyline. But its very familiarity can sometimes obscure its most powerful messages. In this episode, I’m joined by Rabbi Dr. Joshua Berman of Bar Ilan University, who offers a fascinating lens through which to revisit Ruth’s story: the world’s most popular fairytale — Cinderella. By comparing the two narratives, Rabbi Berman uncovers striking parallels and, more importantly, profound differences that...
info_outline
Can Physics Demonstrate God's Existence? (248)
Orthodox Conundrum
Can science be a vehicle to get closer to God? The Rambam famously answered in the affirmative. In the second of the 1000 chapters of his Mishneh Torah, Hilchot Yesodei HaTorah chapter 2, the Rambam writes, “What is the method towards loving and fearing God? At the moment that a person investigates His wondrous and massive actions and creations, and sees through them His endless and infinite wisdom, he immediately loves, praises, and extols, and desires tremendously to know the great Name. In the words of David, ‘My soul thirsts for God, the living divine.’ And when he thinks about these...
info_outline
Having “The Talk”: How Should Jewish Parents Talk to Kids About Sex? (Co-produced with Intimate Judaism)
Orthodox Conundrum
Please note that this episode discusses sensitive topics and uses explicit language. Listener discretion is advised. Today, the Orthodox Conundrum is releasing a new episode of Intimate Judaism that my Intimate Judaism co-host, Talli Rosenbaum, and I recorded with Yonina Rubinstein, where we explore how parents can approach conversations about sexuality with sensitivity, clarity, and confidence. How can we talk to kids about sex in a way that’s honest, healthy, and grounded in Jewish values? Yonina offers practical strategies for different ages and stages, explains the importance of modeling...
info_outline
The Pope, the Jews, and Israel: What to Anticipate From Pope Leo XIV, with Dr. Malka Simkovich (BONUS EPISODE)
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...
info_outline
"You Can't Suppress the Light": The Radical Messages of Rav Kook for Orthodox Jews Today, with Professor Marc Shapiro (247)
Orthodox Conundrum
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,...
info_outline
Inside the Real Rules of War: Colonel John Spencer vs. Media Myths About Israel and Hamas (246)
Orthodox Conundrum
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...
info_outlineI’m doing something a little different this week. Instead of discussing an issue in the Jewish world, I want to offer some inspirational words about the Seder as we enter the final week before the beginning of Pesach. To that end, I invited several of my podcast guests from the past year to present ideas that they find meaningful, with the hope that they will enhance your own Seder as we navigate celebrating Pesach during this challenging moment in Jewish history.
In this episode, you will hear divrei Torah from Dr. Yosefa Fogel Wruble, Olivia Friedman, Rabbi Yitzchak Shurin, Rabbi Dr. Judah Goldberg, Rabbi Ben Kelsen, David Bloom, Rabbi Dr. Rafi Zarum, and Rabbi Chayim Soloveichik. You can look in the show notes that accompany this podcast to see the time signatures for each dvar Torah. I hope and expect that their words of Torah and encouragement will resonate with you, and that they will give you additional ideas to think about as we prepare for the Pesach Seder this year.
Timestamps for the divrei Torah:
2:06 - Rav Kook on internal freedom (Dr. Yosefa Fogel Wruble)
4:49 - Israel as God's first born child (Dr. Yosefa Fogel Wruble)
11:12 - Ha Lachma Ana (Olivia Friedman)
19:37 - Starting with disparagement and ending with praise (Rabbi Yitzchak Shurin)
28:11 - V'hi She'amda (Rabbi Dr. Judah Goldberg)
38:12 - The Ten Plagues (Rabbi Benjamin Kelsen)
55:13 - Dayeinu (David Bloom)
1:00:24 - Pesach, Matzah, u'Maror (Rabbi Dr. Raphael Zarum)
107:23 - Miyagon l'simcha (Rabbi Chayim Soloveichik)
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