The Long Game with Jake Sullivan and Jon Finer

New York Times reporter Jonathan Swan, co-author, along with Maggie Haberman, of the bestselling book Regime Change: Inside the Imperial Presidency of Donald Trump, joins Jake Sullivan and Jon Finer following Democrats’ sweeping midterm victory. As results continue to come in, they examine what drove the Republican defeat and what it means for Trump’s final two years in office. After the Iran war fractured Trump’s winning coalition, what can a Democratic Congress do to constrain a president with broad power over foreign policy? Drawing on his reporting inside the White House, Swan explores the tension between political weakness and presidential power. Then, in The Wrap, Jake and Jon revisit their predictions, flag stories to watch, and share recommendations for what to read and watch. Upgrade to The Long Game+ on Apple to support the show and access exclusive audio segments. This week, Jake and Jon discuss the latest news from Iran. Is further US military escalation on the horizon? Join us on Substack for…

Michael Kofman, defense analyst at the Carnegie Endowment for International Peace, returns to The Long Game as Russia intensifies its bombardment of Ukraine and decisions made in Washington reshape Kyiv’s ability to fight. Kofman examines the gap between Russia’s military performance and its demands at the negotiating table; the leverage each side currently holds and the deadly consequences of throttling Ukrainian access to SpaceX’s Starlink and StarShield. Upgrade to The Long Game+ on Apple to support the show and access exclusive audio segments. Join us on Substack for video versions of exclusive podcast segments, transcripts, and more: https://thelonggame.substack.com/ Watch the video version of this episode on YouTube: https://www.youtube.com/@podlonggame 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. References and supplemental materials Alexander Ward, Natalie Andrews,…

Israelis are preparing to vote in their first election since the October 7 terrorist attacks. Barak Ravid, global affairs correspondent for Axios, joins Jake and Jon to discuss the stakes of the election. Will Benjamin Netanyahu be re-elected for a historic seventh term as prime minister? With polls exceedingly close, Barak explains the challenge Netanyahu’s opposition will face in translating their electoral support into a governing coalition. He also weighs in on what the elections will mean for Palestinians in the West Bank and Gaza and the future of Pres. Trump’s Middle East agenda. Drawing on his deep-sourced reporting and decades covering Israeli politics and the US-Israel relationship, Barak says October 7 is on the ballot and next week’s election will determine the future of Israeli democracy. Access to video versions of exclusive podcast segments, transcripts, and more on Substack: https://thelonggame.substack.com/ Watch the video version of this episode on YouTube:…

President Trump has struck a diesel deal with Russia as fuel prices squeeze Americans. But what does easing restrictions on Russian exports mean for Ukraine and for efforts to end the war? Jake Sullivan and Jon Finer examine the deal’s potential economic impact, the growing tension between Washington and Kyiv, and the prospects for an energy ceasefire as winter approaches. Then, renewed fighting between Saudi Arabia and the Houthis raises difficult questions about American commitments in the Middle East. With Saudi airports and energy infrastructure under attack, could the United States or Israel enter the fight? What could either accomplish? Finally, an Options Memo for NATO’s Secretary General: How should the alliance respond if Russian sabotage kills civilians in a member country? Jake and Jon weigh “light,” “medium,” and “heavy” responses, exploring the challenge of restoring deterrence without triggering a wider war. Listen for the hard choices behind the headlines and the risks each carries. Access to…

Javier Blas, Bloomberg Opinion’s energy and commodities columnist, joins Jake Sullivan and Jon Finer to explain why the Iran war has produced an oil market few expected: crude prices hovering around $100 a barrel while tankers are braving missile attacks, and sharper pain for people buying diesel, jet fuel, and heating oil. How has China’s retreat from the oil market changed the pressure on Washington and Tehran? Why are some traders reluctant to bet on higher prices even when they fear escalation? And how long can the improvised system keeping oil moving through the Strait of Hormuz hold together? Access to video versions of exclusive podcast segments, transcripts, and more on Substack: https://thelonggame.substack.com/ Watch the video version of this episode on YouTube: https://www.youtube.com/@podlonggame 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: Patrick…

Anne Applebaum, Pulitzer Prize-winning author and staff writer at The Atlantic, joins Jake Sullivan and Jon Finer to discuss how far-right ideology and private profit have become intertwined in the Trump administration’s approach to the world; the subject of her new cover story for The Atlantic. They also examine the opaque U.S. oil arrangements in Venezuela, the campaign for political influence in Greenland, and the difficult work of rebuilding American institutions and alliances after Trump. For paid subscribers, Jake and Jon continue their conversation with Anne Applebaum. She details what changes to the White House and the Kennedy Center reveal about political power and culture in Washington.Subscribe to Long Game + on Apple or Substack for access and to support the show. Access video versions of exclusive podcast segments, transcripts, and more on Substack: https://thelonggame.substack.com/ Watch the video version of this episode on YouTube: https://www.youtube.com/@podlonggame Email Jake and Jon at…

PHOTO CREDIT China experts Jessica Chen Weiss, David M. Lampton Professor of China Studies at Johns Hopkins SAIS, and Julian Gewirtz, fellow at Harvard’s Belfer Center and senior research scholar at Columbia University, join Jake Sullivan and Jon Finer ahead of Chinese President Xi Jinping’s state visit to Washington. What does Xi hope to secure from President Trump—and what should the United States seek in return? Could the current truce become a durable détente, or is the relationship moving in two directions at once: greater stability at the top and deeper competition underneath? And as concern grows about advanced AI, can Washington and Beijing reduce the risks without resolving their fundamental distrust? The conversation also examines Taiwan, rare-earth export controls, China’s expanding global role, and the choices that could shape the relationship long after this week’s summit. For paid subscribers, Jake and Jon break down President Trump’s United Nations General Assembly speech in a special segment.…

Julia Curlee, a former CIA analyst and acting senior director at the National Security Council, joins Jake Sullivan and Jon Finer to explain why she believes America’s intelligence system is being weakened from within. Curlee also discusses her experience briefing Vice President Mike Pence and why she left government after nearly 20 years. After the interview, Then to argue for and against reaching a deal with the U.S. and continuing Beijing’s open-weight strategy. Access video versions of exclusive podcast segments, transcripts, and more on Substack: https://thelonggame.substack.com/ Watch the video version of this episode on YouTube: https://www.youtube.com/@podlonggame 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 : Julia Curlee Learn more about your ad choices. Visit podcastchoices.com/adchoices

25 Years After 9/11: Admiral McRaven’s Warning for America Retired Admiral William H. McRaven, former commander of U.S. Special Operations Command and Joint Special Operations Command, joins Jake Sullivan and Jon Finer as the country marks the 25th anniversary of 9/11. McRaven recalls watching the attacks while recovering from a parachute accident, and later planning and executing the operation that brought Osama bin Laden to justice. They also examine why the Trump administration’s unexplained removal of senior military leaders could weaken candid advice and military preparedness; how special operations must adapt from counterterrorism to competition with major powers; and why America’s alliances remain essential to its security. Access video versions of exclusive podcast segments, transcripts, and more on Substack: https://thelonggame.substack.com/ Watch the video version of this episode on YouTube: https://www.youtube.com/@podlonggame Email Jake and Jon at longgame@voxmedia.com. Follow The Long Game so…

Treasury Secretary Scott Bessent says the U.S. is entering “the endgame” with Iran, launching what he calls an “economic D-Day.” Closer to home, U.S.-Canada trade talks have collapsed after Prime Minister Mark Carney rejected Washington’s latest demands. Jake Sullivan and Jon Finer examine whether Operation Economic Outcast can change Iran’s calculus, why China holds the key, and why Canadians are backing a trade fight they expect to hurt. They also stage a Red Team/Blue Team debate over President Trump’s new cyber memo, which allows private companies to conduct offensive operations against foreign cybercriminals. Jon makes the case for the so-called cyber privateers, while Jake lays out the risks. Subscribe to The Long Game+ on Apple podcasts or on Substack for access to exclusive segments. This week, Jake and Jon tackle two listener questions: What should we make of CIA Director John Ratcliffe’s unannounced trip to Moscow? And, how did Jake and Jon manage the physical and mental toll of their years as…

Acclaimed investigative journalist and New Yorker staff writer Patrick Radden Keefe joins Jake Sullivan and Jon Finer to discuss his new book, London Falling. They discuss London’s dirty-money economy, “Say Nothing” and the unfinished business of the Good Friday Agreement, whether the CIA helped spread the Scorpions’ “Wind of Change” behind the Iron Curtain, what a year inside the Pentagon taught Patrick about Washington, and why powerful people rarely see themselves as villains. At the end, Patrick, Jake and Jon share their summer reading list. In an exclusive segment for subscribers to The Long Game+ on Apple or Substack: Patrick, Jake, and Jon examine how Trump-era impunity and outrage fatigue can normalize corruption. Access to video versions of exclusive podcast segments, transcripts, and more on Substack: https://thelonggame.substack.com/ Watch the video version of this episode on YouTube: https://www.youtube.com/@podlonggame Email Jake and Jon at longgame@voxmedia.com. Follow The Long Game so you…

Polish Deputy Prime Minister and Foreign Minister Radosław “Radek” Sikorski joins Jake Sullivan and Jon Finer to assess Europe’s security at a moment of growing strain in the transatlantic alliance. They discuss whether Europe can deter Russia with a reduced US military presence, how NATO should respond to Russian sabotage and possible false-flag operations, and whether America can still be counted on if Article 5 is tested. Sikorski also lays out Ukraine’s possible path to victory, the pressure building on Russia’s economy, the prospects for tougher sanctions, China’s leverage over Vladimir Putin, and why he sees the European Union as a strategic shield for Poland and Ukraine. Then, Jake and Jon discuss Sikorski’s strikingly cautious assessment of the US commitment to NATO—and revisit the closest they came to an Article 5 crisis while serving in the Biden administration. For subscribers to The Long Game+ on Apple Podcasts: Jake and Jon break down the FCC’s new restrictions on foreign-made humanoid robots…

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…

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…

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

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…

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

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…

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…

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…

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…

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…

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…

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

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

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

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

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…

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

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…

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…

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…

Iran expert Karim Sadjadpour joins the show to unpack the U.S.–Israel strikes that killed Supreme Leader Ayatollah Ali Khamenei, Iran’s retaliation across the Middle East, and the uncertainty surrounding what comes next in the war. They discuss: What happens to the Islamic Republic after the loss of its supreme leader? Is the regime likely to fracture, harden, or consolidate — and how far might retaliation go? Can the Revolutionary Guards hold the system together? And what are ordinary Iranians thinking as violence escalates? In a final segment, Jake and Jon turn to Washington, where a standoff between Anthropic and the Pentagon raises significant policy questions about AI, national security, and who sets the rules. What does the “supply chain risk” threat mean — and what precedent does this set for frontier AI companies working with the U.S. 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 of the episode are…

Joint U.S.-Israel strikes on Iran, Iran’s retaliation across the region, War Powers Act debate on Capitol Hill. In this recording of a live conversation on Substack, Jake Sullivan and Jon Finer break it all down: What we know so far, what we don’t know, and the biggest questions that will shape what happens next. Topics of discussion include: - What’s the end game? If the U.S. is entering a war, the public needs a clear account of why, what success looks like, and how this strategy plausibly achieves it. - Is there an imminent threat to the U.S.? Based on the administration’s own claims, there isn’t one from the nuclear program. - Why didn’t the administration seek Congressional authorization? Even President George W. Bush got authorization for the Iraq War. - What to watch for in the coming days as details firm up: To what extent have Iran’s capabilities been degraded? Will Iran close the Strait of Hormuz or otherwise disrupt oil shipping infrastructure? Is Ayatollah Khamenei alive? - The long game…

President Trump’s SOTU speech, war with Iran, cartel violence in Mexico, and a high-stakes standoff between the Pentagon and AI company Anthropic, Jake and Jon break it all down In this week’s episode, they: - React to the foreign policy section of Trump’s State of the Union address - Lay out a forceful case against U.S. military strikes on Iran - Examine the fallout from the killing of Mexican cartel leader “El Mencho” — and how President Sheinbaum is faring under mounting pressure from the U.S. - Break down the Pentagon’s showdown with Anthropic over the company’s restrictions on mass surveillance and autonomous lethal weapons. 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, coming soon. 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…

China, AI, sand — and a 10% chance of UFOs? Jake and Jon are joined by economist and public intellectual Tyler Cowen for a wide-ranging conversation about the structural forces reshaping geopolitics and the balance of power. From the rivalry between China and the United States to the unglamorous constraints of supply chains, they step back from the headlines to ask what will actually define the long game. Together, they take on a series of core questions: - China: What does China actually want? Are the U.S. and China headed for decisive conflict — or a long stalemate over Taiwan and the balance of power in Asia?- AI: Is the AI “race” winner-take-all? How much does being first at the frontier matter — and would any U.S. edge be durable or just a temporary window? - Supply Chains & State Capacity: Can America realistically build resilience in critical inputs, from rare earths to sand? And does the U.S. government still have the institutional capacity to execute in an era of rapid change? - UAPs: How seriously…

Iran at a breaking point—and a bizarre airspace shutdown in Texas. As diplomacy and the threat of military action converge around Tehran, Jake and Jon are joined by journalist Yeganeh Torbati for a ground-level look at the widening gulf between the Iranian people and the regime. Together they: Examine internal unrest and what it means for the regime’s durability. Assess whether Tehran is seeking a deal—or buying time. Explore how a younger, more hardline generation inside the Revolutionary Guard could shape escalation. Then, from Tehran to Texas, Jake and Jon unpack the FAA’s brief closure of airspace over El Paso—tracing it to a Pentagon laser test, a suspected cartel drone, and a revealing case of bureaucratic dysfunction. Follow The Long Game so you never miss an episode. New episodes drop on Fridays. Watch the video of this episode on Youtube. Show notes of the episode are available here. Transcript here, coming soon. The Long Game book recommendations here. Join us on Substack Email Jake and Jon with…

The geopolitics of the Winter Olympics and a pivotal moment in U.S.-Iran diplomacy. As global attention turns to the Games and the possibility of U.S. military action in Iran, Jake and Jon: Explore how sport, soft power, and international conflict intersect. Run a Red Team/Blue Team exercise from Iran’s perspective as nuclear negotiations with the U.S. get underway in Oman. Taking on the roles of Iranian advisers to the Supreme Leader Ali Khamenei, they weigh the risks of striking a deal against the dangers of refusal. Follow The Long Game so you never miss an episode. New episodes drop on Thursdays. Watch the video of this episode on Youtube. Show notes of the episode are available here. Transcript here, coming soon. 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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jake Sullivan and Jon Finer are joined by Evan Osnos to examine a domestic flashpoint in Minnesota and a sudden purge at the top of China’s military. They explore what unrest at home and ideological tightening in Beijing reveal about power, loyalty, and America’s global standing, and debate whether Xi Jinping’s removal of his top general (and former friend) Zhang Youxia lowers or raises the odds of China invading Taiwan. Follow The Long Game so you never miss an episode. New episodes drop on Thursdays. Watch the video of this episode on Youtube. Show notes of the episode are available here. Transcript here, coming soon. 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

Jake Sullivan and Jon Finer unpack Trump’s Greenland gambit and the strain it has placed on NATO and America’s closest partners. They situate the crisis within a one-year assessment of Trump’s foreign policy and debate whether pressure and tariffs are advancing U.S. interests — or undermining the alliance system that has long underpinned American power. Follow The Long Game so you never miss an episode. New episodes drop on Fridays. Show notes and a transcript of the episode are available here. Watch the video of this episode on Youtube. Join us on Substack Email Jake and Jon with your thoughts and questions at longgame@voxmedia.com. Or leave a comment below. Transcript here, coming soon. Note: This episode was taped early afternoon on Wednesday, January 21, prior to Trump’s announcement of reaching a framework deal with NATO Secretary General Rutte. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jake Sullivan and Jon Finer examine the rapidly unfolding crisis in Iran, from nationwide protests and an information blackout to the regime’s brutal crackdown. They place the moment in historical context and debate the central question now facing Washington: whether U.S. military action would protect protesters — or risk escalation without changing realities on the ground. Follow The Long Game so you never miss an episode. New episodes drop on Fridays. Show notes and a transcript of the episode are available here. Watch the video of this episode on Youtube. Join us on Substack Email Jake and Jon with your thoughts and questions at longgame@voxmedia.com. Or leave a comment below. Transcript here, coming soon. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode, Jake Sullivan and Jon Finer discuss the U.S. special operations raid that captured Nicolás Maduro and the Trump administration’s claim that the U.S. will now “run” Venezuela. Drawing on their experience in the White House, they assess the operational risks of the capture, unclear end state, and the limits of the promised economic upside. The conversation widens to Greenland and what the administration’s refusal to rule out force could mean for U.S. power and global stability. Follow The Long Game so you never miss an episode. New episodes drop on Fridays. Show notes and a transcript of the episode are available here. Watch the video of this episode on Youtube. 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

In this episode, Jake Sullivan and Jon Finer cover: - The fast-escalating U.S. pressure campaign against the Maduro regime in Venezuela — including the growing American military buildup and Trump’s post calling Venezuela a “foreign terrorist organization.” - President Trump’s decision to allow the sale of Nvidia’s advanced H200 AI chips to China — announced on the same day that the DOJ called the chip a cornerstone of “AI superiority.” - A Red Team/Blue Team exercise on the U.S.-backed peace proposal for the Ukraine–Russia war, with Jake and Jon stepping into the roles of advisers to Zelensky and Putin. Follow The Long Game so you never miss an episode. New episodes drop on Fridays. Show notes and a transcript of the episode are available here. Watch the video of this episode on Youtube. REFERENCES & SUPPLEMENTAL MATERIALS: - Interview with Christopher Fouqet “Bloomberg Talks: Christophe Fouqet,” December 12, 2025. “U.S. authorities shut down major China-linked AI tech smuggling network,” Department of…

In this episode, Jake Sullivan and Jon Finer cover: - The U.S. “double tap” strike on a boat in the Caribbean that reportedly killed two survivors, raising questions about potential war crimes, and Congress’s response - Trump’s newly released 2025 National Security Strategy - The Trump Administration’s decision to greenlight the sale to China of Nvidia’s powerful H200 chips used in AI Then, a lightning round of questions for each other. Follow The Long Game so you never miss an episode. New episodes drop on Fridays. Show notes and a transcript of the episode are available here. Watch the video of this episode on Youtube. Join us on Substack Email Jake and Jon with your thoughts and questions at longgame@voxmedia.com. Or leave a comment below. Transcript here, coming soon. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode, Jake Sullivan and Jon Finer cover: - Deadlock between Russia and Ukraine as war continues - Rising Japan–China tensions over Taiwan and what Trump’s response signals for U.S. strategy in the region. - Red Team/Blue Team debate on whether the U.S. should maintain, abandon or thicken “strategic ambiguity” toward Taiwan. Follow The Long Game so you never miss an episode. New episodes drop on Fridays. Show notes and a transcript of the episode are available here. Watch the video of this episode on Youtube. Have a question for Jake or Jon? Email us at longgame@voxmedia.com or leave us a comment on Substack. The Long Game is produced by the Vox Media Podcast Network. Episode images source: Getty Images Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode, Jake Sullivan and Jon Finer cover: - Who gained what after Trump’s meeting with Saudi Crown Prince MBS? - How does the corruption scandal inside Zelensky’s government intersects with a new U.S. push for a Ukraine peace deal? - Tabletop: the risks of re-orienting the national-security apparatus to immigration enforcement. Follow The Long Game so you never miss an episode. New episodes drop on Fridays. Show notes and a transcript of the episode are available here. References and Supplemental Readings: - “Disrupting the first reported AI-orchestrated cyber espionage campaign” Anthropic Report, 11/13/25. - “The Risky Movement to Make America Nuclear Again,” Michael Riley in Bloomberg News, 10/30/25. Watch the video of this episode on Youtube. Have a question for Jake or Jon? Email us at letters@cafe.com or leave us a comment on Substack. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode, Jake Sullivan and Jon Finer break down: - Syrian President Ahmed al-Shara’s Oval Office meeting with President Trump, - Trump’s upcoming meeting with Saudi Prince Mohammed Bin Salman and the country’s tech diplomacy, and - Trump’s post about U.S. testing nuclear weapons. They also debate whether Israel should mount more strikes on Iran’s nuclear facilities. Follow The Long Game so you never miss an episode. New episodes drop on Fridays. Show notes and a transcript of the episode are available on Substack. Watch the video of this episode on Youtube. Have a question for Jake or Jon? Email us at letters@cafe.com or leave us a comment on Substack. The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In their first episode, Jake Sullivan and Jon Finer tackle three flashpoints central to U.S. national security interests right now: U.S. / China relations, the Russian - Ukraine War and the situation unfolding in the Caribbean and the Eastern Pacific Ocean. They close with a discussion about the new Netflix film A House of Dynamite, a story about crisis decision-making that, for two people who’ve lived those moments, hits uncomfortably close to home. Follow The Long Game so you never miss an episode. New episodes drop on Fridays. Show notes and a transcript of the episode are available on Substack. Watch the video of this episode on Youtube. Have a question for Jake or Jon? Email us at letters@cafe.com. The Long Game is brought to you by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices

“The Long Game” is a weekly national-security podcast hosted by Jake Sullivan and Jon Finer, former top White House advisers who’ve sat with the president for the classified Presidential Daily Brief and helped turn raw intelligence into real-world policy. Each episode offers an insider’s tour of how consequential decisions get made and why they matter. Learn more about your ad choices. Visit podcastchoices.com/adchoices