Episodes

  • Iran Ceasefire Explained: Winners, Losers, and What Comes Next

    Iran Ceasefire Explained: Winners, Losers, and What Comes Next
    Apr 9 2026
    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 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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    1 hr and 13 mins
  • Trump's Iran Speech & Debating the Deal

    Trump's Iran Speech & Debating the Deal
    Apr 2 2026
    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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    1 hr and 14 mins
  • "Chasing the Dragon" In Iran (with Sen. Ruben Gallego)

    "Chasing the Dragon" In Iran (with Sen. Ruben Gallego)
    Mar 27 2026
    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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    1 hr and 3 mins
  • The Iran War Energy Crisis Is Here (with Helima Croft)

    The Iran War Energy Crisis Is Here (with Helima Croft)
    Mar 19 2026
    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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    1 hr and 18 mins
  • America Doesn’t Understand Iran And It Shows (with Danny Citrinowicz)

    America Doesn’t Understand Iran And It Shows (with Danny Citrinowicz)
    Mar 12 2026
    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, 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
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    1 hr and 12 mins
  • Iran After Khamenei & Pentagon vs. Anthropic (with Karim Sadjadpour)

    Iran After Khamenei & Pentagon vs. Anthropic (with Karim Sadjadpour)
    Mar 5 2026
    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
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    1 hr and 12 mins
  • The Iran Strikes Explained - Live

    The Iran Strikes Explained - Live
    Feb 28 2026
    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
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    23 mins
  • Mexico, Iran, Anthropic and the SOTU Signals

    Mexico, Iran, Anthropic and the SOTU Signals
    Feb 25 2026
    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
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    1 hr and 15 mins