Dilemma Podcast

In this conversation, Joseph Margulies and I explore the difficult moral territory at the heart of his new book Cast Out: A Call for a Forgiving Society in an Age of Incarceration. What does a society gain—or lose—when it decides that certain people are beyond redemption? We talk about the stories of people Margulies encountered through his work, including Lisa Montgomery, David Medina, Klete Keller, Lucas Whaley, and E...

Luke Kemp is a researcher of existential risk whose work spans the rise and fall of civilizations, the psychology of empire, and the future of humanity. In this wide-ranging conversation, we explore whether history follows deeper patterns than we usually recognize—from the Paleolithic origins of human society and the agricultural revolution to the emergence of empires, colonialism, capitalism, and today's "Silicon Goliaths." ...

Michael Sawyer is the author of The Door of No Return, a sweeping work that challenges conventional ideas about race, history, memory, and modernity. In this conversation, we explore his concept of anti-Blackness as something deeper than prejudice or discrimination—an organizing logic embedded within the modern world itself. Sawyer explains why the Middle Passage remains central to understanding contemporary society, dismantl...

In this essay, I respond to Sam Harris's recent comments on Israel, Gaza, Hamas, and why he refuses to debate many of his critics. My argument is not primarily about genocide, proportionality, international law, or even the details of Israel's military response. It is about something more fundamental: the framing of violence itself.Sam Harris often frames Hamas and similar movements as expressions of jihadism—forms of violenc...

For decades, the word "genocide" has occupied a unique place in international law, collective memory, and political debate. But what exactly does it mean—and has the definition become too narrow to describe the forms of violence we witness today? In this conversation, Holocaust and genocide scholar Dirk Moses joins me to discuss the crisis unfolding within genocide studies, the fierce disputes over how the term should be defi...

Born in Iran in 1974, just years before the Iranian Revolution transformed the country forever, Trita Parsi has spent his life at the intersection of some of the most consequential political conflicts of the modern era. In this conversation, we trace his journey from childhood in pre-revolutionary Iran to exile and life in Sweden, exploring how displacement, identity, and history shaped his understanding of power, nationalism, and ...

In round two with Rabbi Yaakov Shapiro, the conversation expands far beyond politics into morality, theology, identity, and the strange psychological world created by modern Zionism. We explore the deep divide between Judaism as a religious covenant and Zionism as a nationalist political project, asking whether the modern state of Israel fundamentally transformed — or even replaced — Judaism for millions of Jews in the ...

In this conversation, Holocaust survivor Stephen Kapos reflects on surviving Nazi-occupied Hungary, the trauma of the Holocaust, and why he believes Israel’s actions in Gaza amount to genocide. Kapos describes the terrifying atmosphere of Budapest in 1944, the yellow star houses, the deportations to Auschwitz, and his family’s connection to the infamous Kastner rescue train, one of the most morally controversial episode...

Philosopher Justin Smith-Ruiu joins me for a deep conversation on Metaphysics, Consciousness, Philosophy of Science, Anthropology of Mind. Psychedelics, Ritual, Religion, Phenomenology, and the limits of modern materialism, centered around his new book ON DRUGS. Drawing on thinkers like Plato, Heidegger, Husserl, Descartes, Leibniz, Huxley, McKenna, and Claude Lévi-Strauss, Smith explores whether psychedelic experiences merely dist...

How do we know what is real anymore?In this conversation with Professor Siwei Lyu of the University at Buffalo, one of the leading researchers in AI generated imagery and deepfake detection, we explore the unsettling world of synthetic images, cloned voices, fake influencers, and manipulated video. From AI girlfriends and scam artists to political propaganda and fake breaking news, we are entering a world where seeing is no longer ...

What is “Muskism”? In this conversation, I sit down with Ben Tarnoff and Quinn Slobodian to unpack the political and moral philosophy behind Elon Musk—not just the man, but the ideology forming around him. Instead of another biography, we explore Musk as a symbol of a broader Silicon Valley worldview shared by figures like Peter Thiel, Alex Karp, and the Palantir elite: a fusion of techno-utopianism, libertarian r...

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 t...

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...

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 act...

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 philoso...

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,...

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 ...

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 activel...

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 qu...