Orthodox Conundrum
Orthodox Conundrum

Orthodox Conundrum

Scott Kahn

Overview
Episodes

Details

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.

Recent Episodes

A $10,000 Bottle of Scotch: Alcohol Abuse, Conspicuous Consumption, and Orthodox Life Today, with Rabbi Jonathan Muskat and Rachel Tuchman (272)
DEC 8, 2025
A $10,000 Bottle of Scotch: Alcohol Abuse, Conspicuous Consumption, and Orthodox Life Today, with Rabbi Jonathan Muskat and Rachel Tuchman (272)

A tragic drunk driving case in Lakewood has pushed an uncomfortable question to the surface. What happens when "Toameha," kiddush clubs and casual drinking culture quietly normalize alcohol misuse in our homes and shuls, especially for the teenagers who are watching us... and what happens when that same culture is surrounded by designer logos, luxury Shabbat tables and endless talk about hotels and vacations? In this episode, I speak with Rabbi Jonathan Muskat and mental health counselor Rachel Tuchman about the growing Toameha phenomenon, problem drinking that does not always look like classic alcoholism, and conspicuous indulgence in luxury in the Orthodox world. Together we explore what all of this is teaching our children about Torah values, tzniut and success, and how parents, educators and communities can begin to change the conversation without pretending that any of us are immune.

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

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82 MIN
Chosen Vs. Unchosen Vs. Rejected: The Idea of a Chosen People in an Antisemitic World, with Rabbanit Yael Leibowitz (271)
DEC 1, 2025
Chosen Vs. Unchosen Vs. Rejected: The Idea of a Chosen People in an Antisemitic World, with Rabbanit Yael Leibowitz (271)

In the past two years many Jews have felt as if the world they thought they knew simply disappeared. Western democracies, universities, and social justice spaces that once seemed welcoming - or at least somewhat neutral - have turned openly hostile toward Israel and the Jewish people. At the center of much of this hatred is a familiar accusation: that Jews think they are chosen, and accordingly, Jews think they are better.

While we wholeheartedly reject the antisemitism implicit in this assertion, we need to honestly confront what the idea of a chosen people means, and what it says about our role on the world stage. Equally important is the question of what the concept of chosenness implies about the other nations of the world which, presumably, are somehow not chosen. Does that mean they're rejected? And for that matter, why did God choose a people in the first place, rather than eliminating the concept altogether?

In this episode I speak with Tanach scholar Yael Leibowitz about what chosenness actually means in the Bible, and what it does not mean. We look at the earliest stories in Bereishit from Cain and Hevel, to the Tower of Bavel, to Abraham, Sodom and Gemorrah, and Saul and Amalek and ask what they can teach us about Jewish distinctiveness, responsibility, and the rage that difference can provoke.

We also talk about how Tanach should and should not be used as a guide to contemporary geopolitics; the danger of turning verses into an inappropriate defense of ultranationalism; and what it means to insist on moral clarity about evil like the atrocities of October 7, while retaining a sense of nuance and avoiding simplistic, reductionist thinking.

In particular, I was fascinated by Yael's contention that the stories of Tanach represent repeating motifs that recur throughout human and Jewish history. In this way, Tanach teaches us as much about the present as about what happened millennia ago. At the same time, Yael openly addresses the flip side of that coin by talking about why certain events in Tanach cannot be seen as norms that should be implemented today.

If you have ever struggled with the idea of the chosen people, or wondered how to defend it in a world that uses it against us, this conversation is for you.

To order Yael's new book Ezra-Nehemiah: Retrograde Revolution, click here.

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

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83 MIN
Painful Questions and Unconditional Love: Orthodox Parents and Their LGBTQ Children, Part Two - with Rabbi Menachem Penner and Rabbi Yakov Horowitz (270)
NOV 24, 2025
Painful Questions and Unconditional Love: Orthodox Parents and Their LGBTQ Children, Part Two - with Rabbi Menachem Penner and Rabbi Yakov Horowitz (270)

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

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104 MIN
Hostility, Confusion, and Ideological Pressure: Outreach in a Changing World, with Rabbi Mark Wildes (269)
NOV 17, 2025
Hostility, Confusion, and Ideological Pressure: Outreach in a Changing World, with Rabbi Mark Wildes (269)

Zohran Mamdani - a politician who openly rejects Israel's right to exist as a Jewish state, yet insists that this has nothing to do with antisemitism - is now the mayor-elect of New York City. He points to a small number of Jewish supporters as evidence, while promoting a worldview in which Israel is framed as a genocidal, apartheid project.

New York is home to the largest Jewish community in the diaspora. When that city elects a proudly anti-Zionist mayor, it sends a message far beyond one municipality. It raises hard questions: What does it mean for Jewish security, for public discourse about Israel, and for the way younger Jews understand the connection between antisemitism and anti-Zionism? Does this moment push more Jews to consider aliyah, or does it demand that they stay and push back? And what does kiruv look like in an atmosphere saturated with hostility, confusion, and ideological pressure?

My guest confronts these questions every day. Rabbi Mark Wildes is the founder of Manhattan Jewish Experience, which has spent decades helping unaffiliated Jews in their 20s and 30s build a deeper relationship with Torah, Shabbat, and the Jewish people. In our conversation, we talk about what he fears will tangibly change on the ground as a result of Mamdani's election, why the supposed split between anti-Zionism and antisemitism is so dangerous, and how Rabbi Wildes speaks to students who are center-left, skeptical about Israel, or openly anti-Zionist.

We also discuss his new book, The Jewish Experience: why he chose to organize basic Judaism around the concepts of God, Torah, prayer, Shabbat, chesed, and tikkun olam; why Shabbat and Jewish wisdom are the best first steps for Jews who feel worn down by the headlines; and how to reclaim tikkun olam from its political distortions without abandoning the real Torah value behind it.

We also look at "spreadsheet kiruv," which emphasizes metrics in determining how successful an outreach program is; how outreach can avoid treating people as projects, and why one small act — a Shabbat meal, a class, even a moment of being pulled into a dance circle — can change a Jewish life in ways none of us may even recognize.

This is a wide-ranging conversation that touches on so many aspects of kiruv, including ma'amarei Chazal, politics, Pet Sounds, and Sgt. Pepper.

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

play-circle icon
69 MIN
Mamdani, Fuentes, Tucker, and Mainstreaming Antisemitism: Jonathan Greenblatt on the Growing Threat from the Left and the Right (268)
NOV 10, 2025
Mamdani, Fuentes, Tucker, and Mainstreaming Antisemitism: Jonathan Greenblatt on the Growing Threat from the Left and the Right (268)

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

play-circle icon
73 MIN