The Long Game with Jake Sullivan and Jon Finer

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  Why Zelensky Fired His War Chiefs & Where Trump's Iran War Goes Next 23.07.2026 53分

  Zelensky just fired his defense minister, his top general, and his prime minister in a single reshuffle — and thousands of Ukrainians poured into the streets. Jake Sullivan and Jon Finer unpack what's really driving it: a generational war over how to fight, Zelensky's wariness of rivals who outshine him, and a reckoning over corruption in military procurement. They trace how Ukraine's homegrown drone industry — now the front line of the war — grew out of a 2023 "tech sprint," and why it may soon make Ukraine one of the world's largest arms exporters. Then, Iran. With the ceasefire dead and the Strait of Hormuz closed, Jake and Jon reopen their "options memo" — keep striking, cut a deal, go for a knockout blow, or walk away.  Subscribe to The Long Game on Substack for access to exclusive podcast segments, transcripts, and more: https://thelonggame.substack.com/ Watch the video version of this episode on YouTube. Email Jake and Jon at longgame@voxmedia.com. Follow The Long Game so you never miss an episode. New episodes drop weekly. The Long Game is produced by the Vox Media Podcast Network. Photo credit: Danylo Antoniuk/Anadolu via Getty Images Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Trump’s Election Playbook, Explained by Jocelyn Benson 15.07.2026 1時間 2分

  Michigan Secretary of State Jocelyn Benson joins Jake Sullivan and Jon Finer to discuss the security of the 2026 midterm elections — just a day before President Trump’s primetime Thursday address, expected to focus in part on “election integrity.” They discuss Trump’s claims about noncitizen voting, the SAVE Act, efforts to access state voter rolls, the dismantling of federal election security infrastructure, and whether federal agents could be deployed to polling places. Then Jake and Jon debate whether Russia might escalate against NATO as Ukraine gains ground — and what that would mean for the alliance. For subscribers to the Long Game+ on Apple: Jake and Jon break down the latest on Iran and the Strait of Hormuz, including the unraveling ceasefire and Trump’s decision to reimpose a blockade of Iranian exports. Subscribe to The Long Game on Substack for access to video versions of exclusive podcast segments, transcripts, and more. Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video version of this episode on YouTube. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Photo credit:  Kent Nishimura / Los Angeles Times via Getty Images Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Heather Cox Richardson on Democracy, Alliances, and America's Future 09.07.2026 36分

  Historian and author of the “Letters From An American” newsletter Heather Cox Richardson joined Jake Sullivan and Jon Finer to discuss the historical roots of today's political moment, the relationship between American democracy and U.S. global leadership, the future of the international order, and what a new foreign policy for the 21st century could look like. Follow The Long Game so you never miss an episode. New episodes drop weekly. For exclusive podcast segments, become a member of the Long Game on Substack or Apple.  Show notes are available here. Transcript here. Watch the video version of this episode on YouTube. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  America at 250: A Net Assessment (w/ Robert Kagan) 01.07.2026 1時間

  As the United States approaches its 250th birthday, how should Americans assess the country's strength, its democracy, and its role in the world? Recorded live at the Aspen Ideas Festival, Jake Sullivan and Jon Finer are joined by historian and foreign policy scholar Robert Kagan for a wide-ranging conversation on America's future. Drawing on four decades of writing about American power and the international order, Kagan argues that the United States is living through two historic shifts at once: a renewed struggle over American identity at home and a retreat from the global leadership that defined the post-World War II era. Topics covered: Whether the United States is entering a genuinely multipolar world The future of NATO, Europe, China, and Taiwan Democratic backsliding and the resilience of American institutions What America's role in the world should look like over the next quarter century Jake and Jon also challenge Kagan on Iraq, Iran, the use of American power abroad, and whether the United States can rebuild trust with its allies after the Trump era. Follow The Long Game so you never miss an episode. New episodes drop weekly. For exclusive podcast segments, become a member of the Long Game on Substack or Apple.  Show notes are available here. Watch the video version of this episode on YouTube. Transcript here. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Timothy Snyder on Iran, Ukraine, and the Future of Freedom 24.06.2026 28分

  Historian and “On Tyranny” author Timothy Snyder joins Jake Sullivan and Jon Finer to discuss the Iran war and ceasefire negotiations, the state of the Russia-Ukraine conflict, how Ukraine has transformed drone warfare, what these wars reveal about the limits of American military power, and what a positive vision of freedom looks like for the United States as it approaches its 250th anniversary.  Follow The Long Game so you never miss an episode. New episodes drop weekly. Show notes are available here. Watch the video version of this episode on YouTube. Transcript here. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Did America Lose the Iran War? (w/ Ambassador Wendy Sherman) 18.06.2026 1時間 12分

  President Trump says the war with Iran is over. But what exactly did the United States agree to? Ambassador Wendy Sherman, the lead U.S. negotiator of the 2015 Iran nuclear deal, joins Jake Sullivan and Jon Finer to assess the new U.S.-Iran agreement and explain why she believes it gives Tehran significant concessions while securing few meaningful nuclear constraints in return. Topics covered: Whether the United States or Iran emerged with greater leverage from the war The future of Iran's nuclear program and its economic windfall through sanctions relief and Strait of Hormuz fees What the deal means for Israel, the Gulf states, and the broader Middle East Why diplomacy requires expertise, patience, and direct engagement with adversaries Jake and Jon also discuss whether Congress will review the agreement, what it could mean for Russia and global energy markets, and other stories they're watching in the weeks ahead. For transcripts, exclusive podcast segments, and more, subscribe to The Long Game on Substack.  On  Apple Podcasts, subscribe to The Long Game+ for exclusive audio. This week, paid subscribers get access to an exclusive segment in which Jake and Jon share behind-the-scenes stories from their own negotiations with Iranian officials during the Obama administration, including late-night bargaining sessions in Vienna, secret talks in Oman, and some of the unexpected moments that helped shape the 2015 Iran nuclear deal. Follow The Long Game so you never miss an episode. New episodes drop weekly. Show notes are available here. Watch the video version of this episode on YouTube. Transcript here. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  What the World Cup Reveals About Global Politics (w/ Franklin Foer) 12.06.2026 48分

  As the World Cup kicks off, what can soccer tell us about the state of the world? Franklin Foer, author of “How Soccer Explains the World,” joins the show to discuss why the world's most popular sport remains one of the best lenses for understanding nationalism, globalization, identity, and political power. More than twenty years after the book's original publication, Foer reflects on how globalization reshaped the game, why national identity remains a powerful force, and what the World Cup reveals about today's geopolitical landscape. Topics covered:  Why globalization often strengthened nationalism rather than weakened it The possibility of a U.S.-Iran World Cup showdown on American soil The roles of Saudi Arabia and Qatar, and the growing intersection of sports and geopolitics President Trump’s relationship with FIFA Subscribe to The Long Game on Substack for exclusive video content, transcripts, and more. This week, paid subscribers receive the inaugural edition of The Wrap, where Jake and Jon share what they're reading, revisit something they may have gotten wrong, and discuss the issues they're watching most closely. Follow The Long Game so you never miss an episode. New episodes drop weekly. Show notes are available here. Watch the video version of this episode on YouTube. Transcript here. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Is Ukraine Now Winning the War Against Russia? (w/Michael Kofman) 04.06.2026 1時間 9分

  More than four years into the Russia-Ukraine war, has the battlefield finally begun to shift? Jake Sullivan and Jon Finer sit down with Michael Kofman, one of the leading analysts of the conflict, fresh off a trip to Ukraine's frontlines. Kofman argues that Ukraine is in its strongest position since 2023 and explains why Russia's grinding offensive may be running out of steam. Together, they discuss how Ukraine used drones and battlefield innovation to offset Russian advantages, why Moscow's military strategy is producing diminishing returns, and what it would take to translate recent developments on the battlefield into a lasting political settlement. They discuss: Why Kofman believes Ukraine has gained the advantage for the first time in years How drones and decentralized defense production have transformed the battlefield Whether Russia can be convinced that continuing the war is futile Subscribe to The Long Game on Substack for exclusive video content, transcripts, and more. This week, paid subscribers will receive a special mailbag segment  where Jake and Jon answer listener questions. Follow The Long Game so you never miss an episode. New episodes drop weekly. Show notes are available here. Watch the video version of this episode on YouTube. Transcript here. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Iran Talks and Trump’s Cuba Strategy w/Ricardo Zúñiga 28.05.2026 1時間 11分

  President Trump is simultaneously pursuing peace talks with Iran while escalating U.S. military pressure in the region following recent strikes. Jake Sullivan and Jon Finer revisit the policy options most likely facing the administration and walk through how they would advise the president at this moment of escalation and diplomacy. Then, Ricardo Zúñiga, former Senior Director for Western Hemisphere Affairs at the National Security Council and one of the architects of the Obama administration’s opening to Cuba, joins to discuss: The politics behind U.S.-Cuba policy  What Obama was trying to achieve through engagement with Havana How Trump’s approach to Cuba and Latin America has changed in his second term The likelihood that the U.S. will undertake some form of military action in Cuba Whether sanctions and pressure campaigns still create meaningful leverage How Venezuela reshaped U.S. thinking about authoritarian regimes in the hemisphere Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video version of this episode on YouTube. Show notes are available here. Transcript coming soon. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  America’s Cybersecurity Crisis Starts With Software (w/Jen Easterly) 22.05.2026 1時間 7分

  President Trump is preparing to sign a major executive order on AI and cybersecurity at a moment of growing concern over cyber threats from China, Russia, Iran, and criminal ransomware gangs. Jen Easterly, former Director of the Cybersecurity and Infrastructure Security Agency and now CEO of RSAC, the world's largest cybersecurity community, joins Jake Sullivan and Jon Finer to discuss: Why America has a software security problem, not just a cybersecurity problem How insecure software shifted risk from tech companies onto consumers Why AI tools like Mythos and GPT-5.5 Cyber could fundamentally change cyber defense What China’s Volt Typhoon campaign revealed about U.S. infrastructure vulnerabilities How cyber warfare has shaped conflicts in Ukraine and Iran Jake and Jon close the episode with a discussion of the latest developments in the Iran war, rising tensions around Cuba, the Ebola outbreak in the Congo, and President Trump’s summit with Xi Jinping in Beijing. Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video version of this episode on YouTube. Show notes are available here. Transcript coming soon. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  China’s Strategy for Trump (w/Kurt Campbell) 13.05.2026 1時間 10分

  President Trump heads to Beijing for a high-stakes summit with Xi Jinping at a moment of growing instability in the Middle East and rising anxiety across Asia. In this episode, former U.S. Deputy Secretary of State Kurt Campbell joins Jake Sullivan and Jon Finer to preview the summit and discuss: Why China increasingly believes the United States is in decline Xi Jinping’s read of Donald Trump Whether Trump might shift U.S. policy on Taiwan or semiconductor export controls How the Iran war is factoring into  China’s strategy  What comes next in the U.S.-China competition Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video version of this episode on YouTube. Transcript here. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. REFERENCES & SUPPLEMENTAL MATERIALS: “How China hopes to win from the war,” The Economist, April 1, 2026. "The Stakes of Trump vs. Xi," Kurt Campbell, Foreign Affairs, May 2026. “Xi Is Planning for China’s Final Victory Over the U.S.,” The New York Times, Julian Gerwirtz, May 13, 2026.  “What a former CIA analyst reveals about a potential China fight,” Max Book Interview with John Culver, The Washington Post, May 11, 2026 “U.S. Intelligence Shows Iran Retains Substantial Missile Capabilities,” Adam Entous, Maggie Haberman, and Jonathan Swan, The New York Times, May 12, 2026. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Iran War & Trump’s Europe Troop Drawdown: What Comes Next? 07.05.2026 1時間 11分

  Iran war developments, including new signs of a potential deal, UAE’s withdrawal from OPEC, and what weeks of conflict have revealed about U.S. leverage. In this episode, Jake Sullivan and Jon Finer discuss: - Why a deal with Iran may be inevitable but harder to reach now - How markets, military risks, and politics are shaping Trump’s strategy - Warnings about depleted U.S. munitions  - Why the UAE is leaving OPEC and what it says about tensions with Saudi Arabia - A Red Team/Blue Team debate on in U.S. reducing troops in Europe Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video of this episode on YouTube. Show notes are available here. Transcript available here. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  China’s Engineering State vs. America’s Lawyerly Society (w/Dan Wang) 29.04.2026 1時間 10分

  Dan Wang, author of Breakneck, breaks down the divide between China’s “engineering state” and America’s “lawyerly society” and what that means for the future of U.S.-China competition. Wang joined Jake and Jon before a live audience at the Endless Frontiers conference in Austin, Texas. In this episode: - Why China builds at scale and why the U.S. often struggles to keep up - The strengths and limits of China’s model, from manufacturing to social policy - A closer look at Xi Jinping’s leadership and decision-making - Why “process knowledge” is key to rebuilding American capacity Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video of this episode on YouTube. Show notes are available here. Transcript coming soon. Join us on Substack. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Debating the War in Iran and U.S. Strategy (w/H.R. McMaster and Matt Pottinger) 22.04.2026 1時間 18分

  H.R. McMaster and Matt Pottinger, former National Security Adviser and Deputy National Security Adviser to President Trump in his first administration, join Jake and Jon for a wide-ranging conversation on Iran, China, and how national security decisions get made at the highest level. Drawing on their time in the White House, they debate the decision to go to war with Iran, the nature of Iran’s nuclear program, and what a successful outcome would even look like. As McMaster puts it, “a lot of times you’re looking at the least bad option.” Follow The Long Game so you never miss an episode.  New episodes drop weekly. Watch the video of this episode on YouTube. Show notes are available here. Transcript coming soon. Join us on Substack. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  John Kerry on Iran, Israel, and Diplomacy 16.04.2026 1時間 15分

  Former Secretary of State John Kerry, who has spent more time negotiating with Iranian leaders than anyone, joins Jake and Jon to discuss the marathon diplomacy efforts that resulted in the JCPOA, Trump’s decision to strike Iran, the likelihood of a deal, the prospects for a two state solution between Israel and Palestinians, and the future of the U.S.-Israel relationship. Then, Jake and Jon discuss Prime Minister Viktor Orban’s surprising defeat in Hungary’s election and what his loss means for the MAGA movement, Trump’s relationship to Europe’s far right, and Ukraine.   Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video of this episode on YouTube. For show notes and transcripts, find and follow us on Substack. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Photo credit: Thomas Imo/Photothek via Getty Images Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Iran Ceasefire Explained: Winners, Losers, and What Comes Next 09.04.2026 1時間 13分

  Jake Sullivan and Jon Finer break down the ceasefire between the United States and Iran, announced Tuesday evening.  They walk through how the deal came together from President Trump’s escalating rhetoric to Pakistan’s role as an unlikely intermediary and assess what the ceasefire actually is, and what it isn’t. They also break down the deeper questions about what the U.S. achieved, what Iran gained, and how this reshapes the strategic balance going forward. Topics discussed: What the ceasefire includes and address the major gaps that remain Why Iran’s control over the Strait of Hormuz may be the most important outcome of the war What could come out of the upcoming negotiations, including the future of Iran’s nuclear stockpile The impact of the war on U.S. deterrence, military readiness, and global credibility The broader implications for Russia, China, NATO, and the U.S.-Israel relationship At the end of the episode, Jake and Jon open up the Long Game mailbag for the first time, answering listener questions on targeted assassinations, Russia’s status as a great power, what’s next for Cuba, and why they started the podcast after leaving the government. Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video of this episode on YouTube. Show notes are available here. Transcript available here. Join us on Substack. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  Trump's Iran Speech & Debating the Deal 02.04.2026 1時間 13分

  One month into the war with Iran, President Trump addressed the nation in prime time — but instead of clarity, the same big questions remain about how this war ends. This week, Jake Sullivan and Jon Finer break down what the president said, what he didn’t say, and what it reveals about where this war is heading. They then take on a Red Team / Blue Team exercise: Jon argues to Iran’s leadership that it should take the deal; Jake makes the hardline case that Iran should stand firm and let America suffer. Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video of this episode on YouTube. For show notes and transcripts, find and follow us on Substack. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Photo credit: Photographer: Alex Brandon/AP Photo/Bloomberg via Getty Images Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  "Chasing the Dragon" In Iran (with Sen. Ruben Gallego) 27.03.2026 1時間 2分

  Senator Ruben Gallego, a Marine veteran of the Iraq War and U.S. Senator from Arizona, joins Jake and Jon to discuss the war in Iran and Congress’s role in decisions of war and peace. Drawing on his experience in one of the hardest-hit units of the Iraq War, Gallego warns that Washington risks repeating the same mistakes. His bottom line: “The best way to support the troops is don’t send us to stupid wars.” They discuss: - How Congress has ceded its war powers to the executive branch and why lawmakers often avoid taking responsibility for decisions on war - The dangers of escalation, and how conflicts can take on a momentum of their own and risk what Gallego calls “chasing the dragon” - What a potential U.S. military operation against Iran could actually look like, and why even “limited” missions may be far more dangerous than expected - Jake and Jon also reflect on their own experience seeking congressional authorization for strikes in Syria, and break down the narrowing set of options facing President Trump, from escalation to a potential off-ramp, and the role of politics, markets, and public opinion in shaping what comes next. Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video of this episode on YouTube.Show notes are available here. Transcript here. Join us on Substack. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. REFERENCES AND SUPPLEMENTAL MATERIALS: Lost: Amelia Earhart’s Three Mysterious Deaths and One Extraordinary Life, by Rachel Hartigan The Hour of the Predator: Encounters with the Autocrats and Tech Billionaires Taking Over the World, by Giuliano da Empoli Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  The Iran War Energy Crisis Is Here (with Helima Croft) 19.03.2026 1時間 18分

  Helima Croft, Head of Global Commodity Strategy at RBC Capital Markets and former CIA economic analyst, joins Jake and Jon as the war with Iran triggers the most severe energy disruption in decades. They discuss: - What happens when the Strait of Hormuz, the world’s most important energy chokepoint, is effectively shut down? How much oil and gas is actually offline, and why there may be no quick fix? - Why markets misread the risks leading up to the war and why oil prices may no longer be a reliable indicator of geopolitical danger. - Who bears the brunt of this crisis, from LNG-dependent economies in Asia and Europe to global supply chains already under strain. Finally, Jake and Jon introduce a new segment: The Options Memo, a look at the kind of choices a president faces at a real inflection point. They lay out 3 paths forward: declare victory and wind the war down, escalate in hopes of forcing de-escalation, or go all in militarily to reopen the Strait of Hormuz. Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video of this episode on YouTube.Show notes are available here. Transcript here. Join us on Substack. Email Jake and Jon at longgame@voxmedia.com. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices
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  America Doesn’t Understand Iran And It Shows (with Danny Citrinowicz) 12.03.2026 1時間 12分

  Former Israeli Defense Intelligence officer Danny Citrinowicz joins the show to assess where the war with Iran stands following the killing of Supreme Leader Ali Khamenei — and what comes next under new leadership in Tehran. They discuss: - Has the campaign reduced the nuclear threat — or increased the likelihood that Iran moves “beyond the Rubicon”? What does the removal of Khamenei mean for Iran’s decision-making? - Are U.S. and Israeli objectives fully aligned — or beginning to diverge? And how should we think about escalation risks, from regional proxies to attacks on critical infrastructure? In a final segment, Jake and Jon run a Red Team/Blue Team exercise on one of the most consequential unresolved questions of the war: - Should the United States consider sending ground troops to secure or neutralize Iran’s enriched uranium stockpile in Isfahan? What would success look like — and what could go wrong? Follow The Long Game so you never miss an episode. New episodes drop weekly. Watch the video of this episode on Youtube. Show notes of the episode are available here. Transcript here.  The Long Game book recommendations here. Join us on Substack Email Jake and Jon with your thoughts and questions at longgame@voxmedia.com. Or leave a comment below.  The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices