Dilemma Podcast

Jay Shapiro

Solving the problems of what to do next with some of today's top thinkers and writers. Hosted by Jay Shapiro.

  1. 13H AGO

    This Rabbi Explains How How Zionism Turned Jews Into Symbolic Human Shields | Yaakov Shapiro

    In this long-form conversation, I sit down with Rabbi Yaakov Shapiro—one of the most outspoken anti-Zionist ultra-Orthodox rabbis—to explore one of the most misunderstood questions in modern politics: what is the relationship between Judaism and Zionism? Raised in suburban American Conservative Judaism with Israeli flags on the bimah, Hebrew school, bar mitzvahs, and an unspoken expectation to support Israel, I wanted to understand what exactly I inherited—and whether it had anything to do with Judaism as a religion at all.We begin with my own family story: my great-great-grandfather, a Satmar Jew in Hungary, was murdered in Auschwitz, while his daughter had left that world decades earlier for America. A few generations later, I inherited a version of Jewish identity shaped less by theology than by Holocaust memory and Zionist politics. Rabbi Shapiro argues that Zionism fundamentally transformed Judaism from a religion of covenant, law, and exile into a political nationalism—and in doing so, created deep moral and philosophical confusion for Jews like me who never believed in the theology but were still expected to defend the state of Israel.From the Holocaust and 1967 to female rabbis, the orange on the Seder plate, chosenness, antisemitism, and whether Judaism is a religion or an ethnicity, this conversation goes far beyond headlines. We discuss whether Zionism is a form of idolatry, why many religious Jews see Israel as a theological violation, and why the phrase “let Judaism be a religion and let Israel be a foreign country” might be the clearest way to understand the crisis. A serious philosophical conversation about faith, identity, history, and the moral catastrophe of Zionism... for the world... and for Judaism.00:00 Coming Up...01:46 Intro My Family Story: Satmar Roots, Auschwitz, and America11:27 My Opening Question: What Did I Actually Get Growing Up?21:13 What Do I Have To Do To Be A Jew?32:14 Jabotinsky and the Zionist Rejection of the “Exile Jew”39:19 I Didn’t Get Judaism—I Got Israel42:11 “Let Judaism Be a Religion, Let Israel Be a Country” Rabbi Shapiro’s Definition of Zionism57:06 Chosen People, Christians, and Jewish Identity01:04:00 Who Gets to Define Who Is a Jew?01:10:29 Are Religious Zionists Actually Religious?01:19:21 Holocaust Identity and Postwar American Judaism01:21:18 Moral Philosophy vs Divine Command01:27:12 Different Roads, Same Conclusion: Zionism Is Wrong01:44:18 The Best Zionist Argument: The Fear of Another Holocaust01:51:24 Would You Go Quietly? Zionists Killing Jews: The Case of Jacob de Haan01:55:48 1967 and the Zionist Transformation of American Judaism01:58:18 Final Thoughts: Obligation, Opportunity, and Another RoundBECOME A MEMBER - MONTHLY MEMBERS ONLY LIVESTREAM https://www.youtube.com/channel/UC5NIku35U9thGG9WBJjE0sw/joinFor more from Jay visit whatjaythinks.com

    1h 60m
  2. 22H AGO

    The Most Absurd Dataset I’ve Ever Seen and A Troubling Truth About Liberation

    The attitudes in American on Israel and Palestine have flipped, we can't ignore the fact that violence may have "worked."There’s a deeply uncomfortable question at the center of political history: is violence ever justified—or even necessary—in the pursuit of freedom? In a widely shared debate, Steven Pinker argues that nonviolent movements are not only more moral, but more effective, citing a dataset from Harvard’s Kennedy School as empirical proof. But when you actually examine that data, the argument starts to unravel. In this essay, I take a close look at how complex resistance movements are reduced to simplistic binaries—success or failure, violent or nonviolent—and how that kind of “counting” can distort reality to produce clean, convenient conclusions... which might be very wrong.Along the way, I explore the psychology of cognitive dissonance, the narratives we build to justify violence, and the difficulty—perhaps impossibility—of measuring something like liberation. This isn’t an argument in favor of violence, but a challenge to the idea that history, morality, and revolution can be neatly captured in a spreadsheet.00:00 Intro00:47 Is Violence Ever Justified?05:18 Pacifism and Violence What is Moral and What Works?07:23 Cognitive Dissonance Explained12:04 Three Pieces of the Argument on Liberation17:03 The Harvard Database25:11 Palestine Liberation and October 7th28:30 The Oppressors Know What They Are Doing31:40 Ghassan Kanafani: Poetry and Armed ResistanceBECOME A MEMBER - MONTHLY MEMBERS ONLY LIVESTREAM https://www.youtube.com/channel/UC5NIku35U9thGG9WBJjE0sw/joinFor more from Jay visit whatjaythinks.com

    37 min
  3. APR 8

    Racism, Memory, and Erasure of the Roma People | The Acceptable Racism in Europe | Margareta Matache

    I went into this conversation knowing almost nothing about the Roma. Which, as it turns out, is kind of an intentional result.Margareta Matache is a historian, author, and one of the leading voices on Roma history and anti-Roma racism. In this conversation, she walks me through a story that most of us were never taught—one that spans centuries of exclusion, slavery, and persecution across Europe.We talk about:Who the Roma actually are (and why that’s a harder question than it sounds)The long history of Roma slavery in EuropeWhy anti-Roma racism still exists—and often goes unnoticedThe role of law and institutions in blocking assimilationThe Roma experience during the The HolocaustAnd how memory, politics, and identity shape what we choose to remember—and what we don’tThere’s also a moment in here where I ask a question that… reveals my own ignorance. She handles it with a level of grace that honestly made the conversation better. We also touch on language—specifically the word “gypsy,” which is controversial and, for many, offensive. The conversation ends with something really powerful: a reading inspired by James Baldwin’s famous letter to his nephew.00:00 Intro 01:36 Why I Held This Conversation Back 02:38 Discovering the Roma Story 04:03 Who Are the Roma? 08:00 Roma Slavery Explained 13:09 Origins: India to Europe 19:43 Poverty, Perception, and Stereotypes 26:59 The Problem with the Word “Gypsy” 33:24 What Is Anti-Roma Racism? 34:13 Why Assimilation Was Blocked 38:27 Race, Identity, and Power 49:03 The Roma in World War II 53:17 The Overlooked Holocaust Experience 01:00:49 Memory, History, and Justice 01:07:06 Baldwin, Letters, and Legacy 01:12:55 Final Reading 01:15:03 Where to Learn More BECOME A MEMBER - MONTHLY MEMBERS ONLY LIVESTREAM https://www.youtube.com/channel/UC5NIku35U9thGG9WBJjE0sw/joinFor more from Jay visit whatjaythinks.com

    1h 17m
  4. APR 6

    Emily Jashinsky: Conservatives and Leftists | What Remains Unbridgeable in the Horseshoe? | Iran War

    This conversation with Emily Jashinsky dives into one of the strangest political moments in recent memory — where parts of the left and right are beginning to sound eerily similar. From “America First” to anti-war sentiment, distrust of institutions, and critiques of empire, we explore whether this convergence is real… or just a temporary alignment before everything snaps back.We get into the deeper philosophical divide driving politics today: how history should relate to the present. Is the United States acting as a global policeman — or an empire? And if it is an empire, can conservatives reconcile that with their own instincts toward nationalism and independence? Along the way, we confront difficult questions around Israel, Iran, the Rapture, Christian Zionism, and the economic realities underpinning global power.The conversation ultimately turns toward moral philosophy — justice, power, religion, and whether peace is something we can achieve, or only something that emerges from a deeper pursuit of justice. This is a rare, open dialogue across ideological lines — not to agree, but to understand before the window for these conversations closes.00:00:00 – Coming Up...00:01:38 – Intro to the Horseshoe00:05:27 – Who is Emily Jashinsky? Background & Political Identity00:09:45 – Where Is the Conservative Movement After Donald Trump?00:16:33 – Did Trump Cross the Line with Iran?00:20:10 – Why Did the U.S. Go to War in Iran?00:23:55 – The Left vs Right Divide on History (1953, Empire, and Iran)00:30:26 – Are Conservatives Breaking Away Over Israel?00:39:22 – Fear, Power, and Human Nature (Hobbes vs Alternatives)00:41:05 – Is Justice Even Possible — Or Just an Illusion?00:47:14 – Can Belief in the “Good West” Survive This Moment?00:54:20 – Why Are We Really at War? Power, Oil, and Economics01:03:23 – Would You Accept Empire If It Fed Your Family?01:11:15 – The Left’s Blind Spots: Religion, Culture, and Third Rails01:15:44 – Where To Find EmilyBECOME A MEMBER - MONTHLY MEMBERS ONLY LIVESTREAM https://www.youtube.com/channel/UC5NIku35U9thGG9WBJjE0sw/joinFor more from Jay visit whatjaythinks.com

    1h 17m
  5. APR 1

    Professor Jiang on His Painful Personal Path | Truth and Myth | A Search for Reality | Internet Fame

    This conversation started with hesitation — both from my audience and from me. Professor Jiang has become a rapidly growing and deeply controversial figure online, with many warning me not to platform him at all. Accusations, clips, and labels were sent my way before we even spoke. So I went into this discussion with an open mind, but also with a responsibility to ask direct questions — about his views on the Holocaust, his use of language, and the frameworks he relies on to interpret the world. What followed wasn’t a takedown or an endorsement, but something more difficult and, I think, more valuable: a real attempt to engage with a lightning rod of narrative rejection.We cover a wide range of ground — from Jiang’s sudden rise on the internet to the deeper roots of how he sees history and power, as well as the painful childhood which shaped him and his battles with depression and alcohol. We get into secret societies, eschatology, and whether ideas like the Illuminati or Freemasons are meant literally or as interpretive tools. We debate the role of myth in shaping reality and national projects — from Masada to the Dead Sea Scrolls to modern geopolitics — and whether narratives around events like the Holocaust have been simplified, mythologized, or politicized in ways that both clarify and distort truth. Throughout, I push back on where I think explanations go too far, while also acknowledging where mainstream narratives can feel incomplete or unsatisfying.But what surprised me most was the personal side of the conversation. Behind the “Professor Jiang” persona is a teacher navigating sudden internet fame, scrutiny, and a very strange digital landscape. We talk about why people are drawn to voices like his right now — a growing distrust in institutions, a sense that official stories no longer hold, and the risk that comes with replacing one form of certainty with another. At its core, this is a conversation about how we search for truth in a world full of competing narratives — and how easy it is to lose our footing in the process.00:00 – Coming Up...02:08 – Intro and Caveats: Who Is Professor Jiang?05:00 – Origins: Childhood, Bullying & Path to Teaching10:22 – Credentials, Titles, and Intellectual Authority "Professor"12:12 – Predicting the Future: How Accurate Are You?14:04 – Secret Societies & Pattern Thinking Freemasons, numerology,20:12 – Myth vs Reality: How We’re Taught History22:40 – Holocaust Questions & the Search for Truth29:37 – When Myth Overtakes Truth33:26 – Masada: A Case Study in Myth-Making39:33 – Do These Frameworks Actually Predict Anything?43:15 – Where Conspiracy Thinking Goes Too Far48:33 – Religion, Power, and Human Behavior Judaism, Islam, and how belief systems shape conflict55:07 – My Own Experience with Judaism Personal reflection, upbringing, and interpretation01:02:27 – Kabbalah, Mysticism, and Meaning01:08:13 – Fear, Freedom, and the Human Condition Erich Fromm, existential anxiety01:10:21 – Should Some Truths Stay Hidden?01:18:16 – The Responsibility of Asking Questions01:23:16 – Why People Are Drawn to Him Now, Distrust, collapsing narratives01:28:18 – Final reflections on Bullsh!t High School History, Dead Sea Scrolls and DoubtBECOME A MEMBER - MONTHLY MEMBERS ONLY LIVESTREAM https://www.youtube.com/channel/UC5NIku35U9thGG9WBJjE0sw/joinFor more from Jay visit whatjaythinks.com

    1h 40m
  6. MAR 29

    Peter Beinart on Epstein's Religion| Israel’s Iran Influence | Judaism at a Breaking Point

    I sat down again with Peter Beinart to talk through what feels like a rapidly escalating and confusing moment — not just politically, but inside Judaism itself. We start with a question I’ve been asking a lot of people lately: how to talk about the Jeffrey Epstein files honestly, without dodging it, but also without feeding into something darker. That opens into a broader conversation about antisemitism, where the line is now, and whether that line has been blurred beyond recognition.From there we get into Judaism as religion vs ethnicity, the weird tension that creates, and how that plays into conversations about power, responsibility, and group identity. We talk about the Talmud, some of the passages that are going viral right now, and why pulling lines out of context is both dangerous and, at the same time, something people are obviously going to keep doing. We also come back to real-world experiences — synagogues, Israeli flags, community pressure, and what it actually feels like to navigate that space right now.At the end we zoom out to Israel, Iran, and where all of this might be heading. Beinart makes the case that you can talk about power, influence, and what Israel is doing without falling into antisemitic thinking — but also acknowledges how hard that’s becoming in the current climate. I’m trying to push on these questions as directly as I can, because I don’t think ignoring them is going to end well.00:00 Coming Up...02:10 Intro to Peter Beinart and Why I Keep Asking about Epstein's Religion06:49 A Flashback to "Not being and A$$hole"13:00 Where Are We Now (Let's Talk Epstein's Religion22:18 Jewish Doctrine and Harm23:19 An Attack on "Jewish Ambulances"30:50 The Talmud Says Some Crazy Stuff38:13 What if a Synagogue Supports Israel Publicly40:55 Religion and Dealing With Having Power46:00 Israel Leading America to War with Iran51:20 Why Didn't Epstein's Jewishness Help Him Not Do Harm?57:22 How Does the War on Iran Affect Jewish Conversation1:00:02 Jewishness as "Ethnicity, Race, Nationality, Religion"BECOME A MEMBER - MONTHLY MEMBERS ONLY LIVESTREAM https://www.youtube.com/channel/UC5NIku35U9thGG9WBJjE0sw/joinFor more from Jay visit whatjaythinks.com

    1h 2m
  7. MAR 29

    The Hiroshima Myth | Israel, Iran Escalation | Why Nukes Are Pointless but Possible - Ward Wilson

    As tensions escalate between Iran, Israel, and the United States, the question of nuclear war no longer feels abstract—it feels immediate. With ongoing strikes, threats to critical infrastructure, and fears of further escalation across the region, the possibility of a nuclear weapon being used is no longer confined to history books. Ward Wilson joins me at a moment where the stakes are not theoretical: governments are actively making decisions that could shape whether this conflict stays conventional—or crosses a line humanity hasn’t crossed in 80 years.But underneath this urgency is something even more unsettling: the possibility that much of what we believe about nuclear weapons—their power, their usefulness, even their role in ending World War II—is based on myths. In this conversation, we unpack those assumptions while looking directly at the present crisis. If nuclear weapons don’t actually “win wars” or meaningfully improve military outcomes, then what exactly would happen if one were used in Iran? Would it change anything—or just kill hundreds of thousands and push the world into something far worse? This is a conversation about how dangerous ideas from the past are shaping decisions right now—and why misunderstanding nuclear weapons might be one of the biggest risks we face today.Ward Wilson Substack: https://substack.com/@wardhayeswilson00:00 – Coming Up01:13 – Intro to Ward Wilson and Next Dilemma Guests06:10 – A Hopeful Start07:10 – The Hiroshima Myth (Did the Bombs End WWII?)18:25 – Do We Overestimate Nuclear Weapons?20:25 – Deterrence Fails23:25 – Cuban Missile Crisis and the Apocalypse29:14 – The Real "Realists"34:03 – Who Actually Has Nuclear Weapons Today?41:40 – Do Nukes Prevent Invasions? (North Korea Argument)47:10 – Iran, Israel, Trump: Real Risk of Use?53:10 – Could Trump Just Press the Button? (No Failsafes?)57:16 – The Psychology of Using Nuclear Weapons01:05:02 – Final Thoughts: Hope vs RealityBECOME A MEMBER - MONTHLY MEMBERS ONLY LIVESTREAM https://www.youtube.com/channel/UC5NIku35U9thGG9WBJjE0sw/joinFor more from Jay visit whatjaythinks.com

    1h 6m
  8. MAR 17

    Jeffrey Sachs: The Psychotic Iran War | Judaism’s “Chosen People” Problem | This Ends How?

    In this wide-ranging conversation, economist and public intellectual Jeffrey Sachs discusses the rapidly escalating conflicts shaping today’s world—from the war with Iran and the crisis in the Middle East to the ongoing confrontation in Ukraine. We explore the deeper forces driving these conflicts, including the role of ideology, religion, and power in shaping modern geopolitics. Sachs also weighs in on controversial questions surrounding Zionism, debates about the idea of “chosenness” in Judaism, and how religious identity and historical narratives influence political decision-making. The discussion also touches on elite power networks, intelligence agencies, and lingering questions surrounding figures like Jeffrey Epstein and the shadowy intersections of influence, politics, and global strategy.Looking back over his extraordinary career advising governments during the economic transitions of Bolivia, Poland, and the former Soviet Union, Sachs reflects on the experiences that shaped his worldview. Once deeply embedded within the global policy establishment, he explains how decades of witnessing power up close—from Washington to Moscow—gradually led him to question the assumptions and incentives driving today’s foreign policy decisions. The result is a candid conversation about the psychology of power, the ideas that motivate leaders, and why Sachs believes the international system is drifting toward increasingly dangerous confrontations.00:00:00 Coming Up...00:01:58 Intro to Jeffrey Sachs00:04:16 Pivot Points and Philosophy Turns in Jeffrey's Life00:10:17 Resentment Toward US Foreign Policy and Deep State00:18:11 Free Market Undermined by Deep State00:27:28 Underestimating Zionism or Greed00:33:33 World War III Is Here?00:43:53 Making Bets We Must Win and War00:50:46 Malthus and Darwin00:55:24 Redistribution and the Elites01:00:45 Why Are There So Many Jews in the Epstein Files01:06:37 Keep Up with Jeffrey SachsJeffrey's Official YouTube https://www.youtube.com/@JeffreyDSachsOfficialBECOME A MEMBER - MONTHLY MEMBERS ONLY LIVESTREAM https://www.youtube.com/channel/UC5NIku35U9thGG9WBJjE0sw/joinFor more from Jay visit whatjaythinks.com

    1h 8m
4.6
out of 5
72 Ratings

About

Solving the problems of what to do next with some of today's top thinkers and writers. Hosted by Jay Shapiro.

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