The Long Game with Jake Sullivan and Jon Finer

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

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 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

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

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

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 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 produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 questions: What are the second-and third order effects? Will this instability lead to increased risks of terrorism, displacement, and downstream political consequences as we saw with the Arab Spring, the Syrian Civil War, and the Iraq War?  What’s the eventual off ramp for the U.S.? What actually happens inside Iran? If the current leadership is toppled, who takes over? And, how is China seeing this – does this create new risks with respect to Taiwan? 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. 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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 should we take unexplained aerial phenomena — and what does it mean to assign a non-zero probability to extraterrestrial explanations without sliding into conspiracy? The episode closes with Cowen in the hot seat for his signature overrated/underrated rapid-fire questions covering a broad sweep of topics. 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.  The Long Game is produced by the Vox Media Podcast Network. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 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

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 Justice Press Release, December 8, 2025. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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