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A NOTE FROM THE PRODUCER

is the Executive Producer of The Long Game

This week, Jake Sullivan and Jon Finer break down Ukraine’s military leadership shakeup, the drone revolution reshaping warfare, and America’s shrinking choices in Iran.

In Ukraine, President Volodymyr Zelensky has dismissed both his defense minister and the commander of the armed forces—an extraordinary reshuffle at a moment when Ukraine has been gaining ground. The personnel fight reflects a larger debate over how the war should be fought: with traditional military tactics or a new model built around drones, autonomous systems, and technological innovation.

“To have both the defense minister and the overall commander of Ukrainian forces fired basically within a week of one another—while the war is going pretty well—that’s a striking thing,” Jake says. The overhaul also raises questions about Zelensky’s management of increasingly popular officials who could someday become political rivals.

Jake and Jon then trace the rise of Ukraine’s drone industry, including the U.S.-backed “technology sprint” they helped launch after the failed 2023 counteroffensive. Jon argues that Ukraine has now “surpassed the United States military, and basically every other military on the planet” in integrating autonomous systems into combat.

Meanwhile, the U.S.-Iran war is intensifying, the Strait of Hormuz remains effectively closed, and more U.S. service members have been killed. Jake and Jon outline President Trump narrowing set of bad choices: escalate, pursue another deal, declare victory and leave, or simply continue exchanging strikes with Iran in the hope that something changes. As Jake puts it: “All of the options are pretty bad, because the choice of getting into this mess in the first place was pretty bad.”

Listen to the episode and share your thoughts and questions. Comment below or email Jake & Jon at longgame@voxmedia.com.

Transcripts here.

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REFERENCES & SUPPLEMENTAL MATERIALS:

YouTube, “2014 Hero of Mariupol Becomes Ukraine’s New Army Chief”

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A NOTE FROM THE PRODUCER

is the Executive Producer of The Long Game

This week on The Long Game, Jake Sullivan and Jon Finer take on a threat that is both foreign and domestic: the security of American elections.

Just as President Trump prepares to deliver a Thursday primetime address expected to focus in part on “election integrity,” Michigan Secretary of State Jocelyn Benson joins the show.

Benson is one of the country’s leading election officials and a frontline target of President Trump’s repeated claims about voter fraud and election rigging. In the episode, she offers a clear bottom line about the 2026 midterms: despite growing threats from disinformation, foreign interference, and sustained federal pressure on state election systems, the election will be free, fair, and secure.

The most dangerous form of election interference, she warns, may not come from “hacking of voting machines,” but what she calls the “hacking of the mind”: efforts to flood the public square with fear and confusion so voters either stay home or stop trusting the result.

In the discussion, they address several key issues, including:

• What would happen if federal agents were sent to polling places

• Whether evidence supports claims about widespread noncitizen voting

• The SAVE Act and how it could make voting harder for eligible citizens

• Trump’s efforts to access voter rolls and pressure state election officials

• The dismantling of federal election security support

Then, Jake and Jon turn abroad for a Red Team / Blue Team debate on Russia, Ukraine, and NATO. They take on the opposing roles of advisers to President Vladimir Putin, arguing for and against Russia escalating against NATO member countries as Ukraine gains more and more territorial ground.

We’d love to hear your thoughts and questions. Please comment below or email Jake & Jon at longgame@voxmedia.com.

Earlier this week, Jake and Jon did a special segment for paid subscribers breaking down the big strategic questions raised by the latest Iran news, including the unraveling ceasefire and President Trump’s decision to reimpose a blockade on Iran’s ports and cargo. You can find it here.

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REFERENCES & SUPPLEMENTAL MATERIALS:

Photo credit: Bill Clark/CQ-Roll Call, Inc via Getty Images

Episode transcript is here.

Jon Finer, “The World Is Cutting Ties With America. It’s Already Costing Us,” NYT, 7/21/26

Marc Caputo, “Trump plans ‘potpourri’ prime-time speech Thursday,” Axios, 7/14/26

“Appeals court upholds dismissal of Trump’s demand for Michigan voter rolls,” Detroit Free Press, 6/24/26

U.S. Court of Appeals for the Sixth Circuit, “United States v. Benson, No. 26-1225,” Justia, June 24, 2026 (Court decision related to the Trump administration’s effort to obtain Michigan voter data from Jocelyn Benson)

William J. Clinton, “Inaugural Address,” The American Presidency Project, January 20, 1993 (Source for the Clinton line Jocelyn Benson paraphrases: “There is nothing wrong with America that cannot be cured by what is right with America.”)

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A NOTE FROM THE PRODUCER

Jennifer Indig is the Lead Editorial Producer for The Long Game

This week on The Long Game, Jake Sullivan and Jon Finer are joined by historian and foreign policy scholar Robert Kagan for a special conversation recorded live at the Aspen Ideas Festival.

As the United States approaches its 250th birthday, Jake and Jon ask Kagan to conduct a “net assessment” of America: Is the country in decline, or is it entering another period of renewal? 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. Looking ahead, he warns that “we are moving into a genuinely multipolar world... where every nation is basically for itself.”

The conversation explores whether the postwar international order is unraveling, the future of NATO and America’s alliances, Russia’s ambitions in Europe, China’s long-term strategy toward Taiwan, democratic backsliding at home, and what America’s role in the world should look like over the next quarter century.

In a special segment for paying subscribers, Jake and Jon close with a lightning round, where Kagan offers quick takes on everything from presidents and power to books, baseball, and a few questions he may not have seen coming.

Comment below or email Jake & Jon at longgame@voxmedia.com.

Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

The World America Made, By Robert Kagan

The Ghost At the Feast: America and the Collapse of World Order, 1900-1941 (Dangerous Nation Trilogy), By Robert Kagan

“America Vs. The World,” Robert Kagan, The Atlantic, January 18, 2026

The Rise and Fall of the Great Powers: Economic Change and Military Conflict from 1500 to 2000, By Paul Kennedy

The National WWII Museum in New Orleans

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A NOTE FROM THE PRODUCER

Jennifer Indig is the Lead Editorial Producer for The Long Game

This week on The Long Game, Jake Sullivan and Jon Finer sit down with Ambassador Wendy Sherman, the lead U.S. negotiator of the 2015 Iran nuclear deal, to break down the new agreement President Trump has reached with Iran following more than three months of war.

Drawing on years spent negotiating directly with Iranian officials, Sherman explains why she believes the deal gives Tehran significant economic and political concessions while securing few meaningful nuclear constraints in return. Comparing the painstaking diplomacy behind the original JCPOA with the Trump administration’s approach, Sherman argues that “when you read the words of what was just agreed to, it’s horrifying what we gave up.”

The conversation explores what it takes to negotiate with adversaries, whether the United States or Iran emerged with greater leverage after the war, the future of Iran’s nuclear program, and what the agreement means for Israel, the Gulf states, and the broader Middle East.

Jake and Jon then react to the conversation, assess the political and strategic implications of the deal, discuss whether Congress will have any role in reviewing it, and identify several stories to watch in the weeks ahead—from mounting pressure on Russia as oil prices fall and reports of Russian sabotage operations in Europe, to an escalating dispute between the Trump administration, the Pentagon, and AI company Anthropic over the future of frontier AI models and national security.

In a special segment for paying subscribers, available Friday morning, 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.

Comment below or email Jake & Jon at longgame@voxmedia.com.

Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

Not for the Faint of Heart: Lessons in Courage, Power and Persistence, By: Ambassador Wendy R. Sherman

“Read: Full text of U.S.-Iran memorandum of understanding,” Axios

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A NOTE FROM THE PRODUCER

Jennifer Indig is the Lead Editorial Producer for The Long Game

This week on The Long Game, Jake Sullivan and Jon Finer sit down with Franklin Foer, author of How Soccer Explains the World, on the eve of the World Cup.

More than twenty years after the book was first published, Foer reflects on why soccer remains such a powerful lens for understanding globalization, nationalism, identity, and political power. As he puts it, many of the “local affinities and tribal affiliations” that observers expected globalization to weaken instead “survived and sometimes became more intense.” Jake and Jon discuss what that insight can teach us about today’s world, from state-backed clubs and sportswashing to immigration, U.S.-Iran tensions, and the politics surrounding this year’s tournament.

Transcript here.

Comment below or email Jake & Jon at longgame@voxmedia.com.

REFERENCES AND SUPPLEMENTAL MATERIALS:

How Soccer Explains the World: An Unlikely Theory of Globalization by Franklin Foer

“Why Does No One Care About the World Cup This Year?” David Wallace-Wells, The New York Times, June 03, 2026

“Soccer Imitates Life,” Henry Kissinger, The Washington Post, June 29, 1986

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A NOTE FROM THE PRODUCER

Jennifer Indig is the Lead Editorial Producer for The Long Game

This week on The Long Game, Jake Sullivan and Jon Finer sit down with Michael Kofman, one of the leading analysts of the Russia-Ukraine war, to assess a conflict that has now entered its fifth year.

Drawing on a recent trip to the frontlines in Ukraine, Kofman argues that the battlefield has shifted in Ukraine’s favor for the first time in years. As he puts it, “Ukraine is in the best position it’s been since summer of 2023,” and for the first time in a long time, “the balance of initiative and the advantage has shifted to Ukraine.” He explains why Russia’s grinding offensive has stalled, how Ukraine used drones and a decentralized defense industry to offset Russian advantages in manpower and artillery, and why Moscow may be running out of effective options on the ground. The conversation explores the evolution of drone warfare, the growing importance of air defense, the risk of Russian escalation against NATO, and whether the war may finally be approaching a meaningful turning point.

Looking ahead, Kofman argues that the key question is whether Russia’s political leadership can be persuaded to adjust its goals to match battlefield realities: “How long will it take the Russian leadership to realize what Ukraine’s been trying to convince them that the war is futile at this point?”

In closing, Jake and Jon then reflect on the conversation, discussing Russia’s increasing use of gray-zone tactics against NATO countries, the challenge of preventing the war from widening beyond Ukraine, and what it would take to translate battlefield developments into a durable diplomatic settlement.

This week, paid subscribers will receive bonus content where Jake and Jon answer listener questions about how they choose sides for their Red Team / Blue Team debates, what a future U.S. president could do to rebuild America’s alliances, the implications of Bill Pulte’s nomination as Director of National Intelligence, and their advice for young people interested in pursuing careers in national security.

Comment below or email Jake & Jon at longgame@voxmedia.com.

Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

“Ukraine Turns the Tide,” Jack Watling, Foreign Affairs, June 1, 2026

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A NOTE FROM THE PRODUCER

Jennifer Indig is the Deputy Editor for The Long Game

This week on The Long Game, Jake Sullivan and Jon Finer begin with an update on the rapidly evolving situation with Iran following recent U.S. strikes alongside simultaneous peace talks to try and end the conflict. Revisiting the policy options currently available to the Trump administration, they walk through how they might advise the president in a National Security Council-style options memo exercise — weighing the risks, probabilities, and potential consequences associated with the paths now on the table. Along the way, they assess the administration’s broader Middle East strategy and discuss the implications for Gulf states and U.S. credibility abroad.

Jake and Jon are then joined by 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. They discuss the politics of 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, and why Zúñiga believes the current pressure campaign could lead to a prolonged crisis — or even military action. The conversation also explores migration, Venezuela, sanctions, and what America’s posture toward Cuba reveals about U.S. strategy in the Western Hemisphere more broadly.

Comment below or email Jake & Jon at longgame@voxmedia.com.

Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

“Exclusive: U.S. eyes attack-drone threat from Cuba,” Marc Caputo, Axios, 5/17/26

You can listen to this episode on Spotify, Apple Podcasts, or other listening apps.

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A NOTE FROM THE PRODUCER

Jennifer Indig is the Deputy Editor for The Long Game

This week on The Long Game, Jake Sullivan and Jon Finer are joined by Jen Easterly, former Director of the Cybersecurity and Infrastructure Security Agency and now CEO of RSAC, the world’s largest cybersecurity community to discuss why America’s biggest cybersecurity challenge may actually be a software security problem. They explore how insecure software created today’s cyber vulnerabilities, why AI tools like Mythos and GPT-5.5 Cyber could change the balance between attackers and defenders, and what threats from China, Russia, and Iran reveal about the future of cyber conflict.

Jake and Jon close the episode with a discussion of the latest developments in the Iran war, tensions around Cuba, the Ebola outbreak in the Congo, and President Trump’s summit with Xi Jinping in Beijing.

Comment below or email Jake & Jon at longgame@voxmedia.com.

Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

“The End of Cybersecurity,” Jen Easterly, Foreign Affairs, October 2025

“The Beginning of the End of Cybersecurity,” Jen Easterly, LinkedIn Post, April 8, 2026

“2028: Two Scenarios for Global AI Leadership,” Anthropic, May 14, 2026

“Deterrance and Dissuasion in Cyberspace,” Joseph S. Nye, International Security 2017

“Early War Goal Was to Install Hard-Line Former President as Iran’s Leader,” Mark Mazzetti, Julian Barnes, Farnaz Fassihi, and Ronen Bergman, New York Times, May 19, 2026

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A NOTE FROM THE PRODUCER

Jennifer Indig is the Deputy Editor for The Long Game

This week on The Long Game, Jake Sullivan and Jon Finer are joined by former Deputy Secretary of State Kurt Campbell to preview President Trump’s summit with Xi Jinping in Beijing. They discuss why China increasingly believes the United States is in decline, what Xi sees when he looks at Trump, the risks surrounding Taiwan and semiconductor policy, and how the Iran crisis is reshaping China’s global strategy.

Comment below or email Jake & Jon at longgame@voxmedia.com.

Follow The Long Game wherever you get your podcasts.

Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

“How China hopes to win from the war,” The Economist, April 1, 2026.

“Xi Is Planning for China’s Final Victory Over the U.S.,” The New York Times, Julian Gerwirtz, May 13, 2026.

“The Stakes of Trump vs. Xi,” Kurt Campbell, Foreign Affairs, May 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.

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A NOTE FROM THE PRODUCER

is the Deputy Editor for The Long Game

This week on The Long Game, Jake Sullivan and Jon Finer unpack the fast-moving Iran war, the search for a diplomatic off-ramp, and whether the United States still has the leverage to shape the outcome. They break down reports of a potential framework deal, the risks of relying on military pressure without a clear endgame, and the economic and strategic costs already piling up.

They also examine the UAE’s decision to leave OPEC and what it reveals about shifting Gulf power dynamics, especially between Abu Dhabi and Riyadh. Then, in light of Trump’s announcement that the U.S. will withdraw 5,000 troops from Germany, Jake and Jon debate whether the U.S. should reduce its troop presence in Europe and what that would mean for NATO, Russia, China, and America’s long-term strategy.

Comment below or email Jake & Jon at longgame@voxmedia.com.

Follow The Long Game on Apple, Spotify or wherever you get your podcasts.

Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

“Exclusive: U.S. and Iran closing in on one-page memo to end war, officials say,” Barak Ravid, Axios, May 5, 2026.

“Trump is 14 days from decisive victory in Iran,” Mark A. Thiessen, The Washington Post, April 30, 2026

“Last Rounds? Status of Key Munitions at the Iran War Ceasefire,” Mark F. Cancian and Chris H. Park, CSIS, April 21, 2026.

“The U.A.E. Stands Up to Iran,” Yousef Al Otaiba, The Wall Street Journal, March 25, 2026.

“The End of the Longest Peace?” Graham Alliosn and James A. Winnefeld, Foreign Affairs, November 24, 2025.

“It’s Only 5,000 Troops, but America Will Come to Regret Its Rash Withdrawal From Germany,” Linas Kojala, The New York Times, 5/2/26.

The Demon of Unrest: A Saga of Hubris, Heartbreak, and Heroism at the Dawn of the Civil War. By Erik Larson

The Splendid and the Vile: A Saga of Churchill, Family, and Defiance During the Blitz, By Erik Larson,

Power and Purpose Podcast with Amanda Sloat and Nathalie Tocci

The View From Here Podcast with Jasmine El-Gamal

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A NOTE FROM THE PRODUCER

is the Deputy Editor for The Long Game

In this week’s episode of The Long Game, Jake Sullivan and Jon Finer sit down with Dan Wang, author of Breakneck, for the show’s first-ever live taping at the Endless Frontiers conference in Austin, Texas.

The conversation begins with Wang’s core argument from his book: that China has become an “engineering state” built to execute at scale, while the United States has evolved into a “lawyerly society” that often struggles to build. Drawing on his years living in China, Wang reflects on how that divide shows up in everything from infrastructure and manufacturing to housing and energy.

They then turn to what each system gets right and wrong. Wang highlights China’s capacity to build and dominate manufacturing, while also confronting the human costs of policies like the one-child policy and zero-COVID. The discussion also offers a more personal window into Xi Jinping, how he operates behind closed doors, his mix of rigidity and political instinct, and what his leadership style reveals about the system he runs.

Finally, the conversation shifts back to the United States and what it would take to compete more effectively. Wang argues that America has focused too much on invention and not enough on “process knowledge,” the practical expertise required to build at scale, and lays out ideas for rebuilding that capacity.

The episode surfaces a deeper tension between two fundamentally different approaches to power, technology, and governance and what that means for the future of U.S.-China competition.

Comment below or email Jake & Jon at longgame@voxmedia.com.

Follow The Long Game wherever you get your podcasts.

Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

Breakneck: China’s Quest to Engineer the Future, By Dan Wang, August 2025

“Litigation Nation, Engineering Empire,” Jonathon P. Sine, Cogitations, August, 25, 2025

“The Real China Model,” By Dan Wang and Arthur Kroeber, Foreign Affairs, September/October 2025

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A NOTE FROM THE PRODUCER

is the Deputy Editor for The Long Game

In this week’s episode of The Long Game, Jake Sullivan and Jon Finer are joined by H.R. McMaster and Matt Pottinger, who respectively served as National Security Adviser and Deputy National Security Adviser in President Trump’s first administration.

The conversation begins inside the White House, with a look at how national security decisions actually get made and what happens when that process breaks down. As McMaster puts it, the goal is to present real choices to the president, even when “a lot of times you’re looking at the least bad option.”

They then turn to Iran, debating the decision to go to war, the nature of Iran’s nuclear program, and what a successful outcome would even look like including the odds of a diplomatic deal in the near term and whether the conflict ultimately leads to regime change.

Finally, the discussion broadens to China and Venezuela, exploring how the war in Iran is shaping U.S. competition with China, and what the U.S. operation in Venezuela reveals about Trump’s approach to foreign policy.

The conversation surfaces a deeper divide, not just over policy, but over basic assumptions about how wars end and how the U.S. should use power. It’s a rare, substantive debate between experienced policymakers approaching the same questions from different perspectives. The episode is a reminder of what a rigorous, civil exchange on national security can look like.

Comment below or email Jake & Jon at longgame@voxmedia.com.

Follow The Long Game wherever you get your podcasts.

Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

Books by H.R. McMaster:

• Dereliction of Duty: Johnson, McNamara, the Joint Chiefs of Staff, and the Lies That Led to Vietnam (1997)

• Battlegrounds: The Fight to Defend the Free World (2020)

• At War with Ourselves: My Tour of Duty in the Trump White House (2024)

Podcasts hosted by H.R. McMaster:

• Today’s Battlegrounds

• GoodFellows: Conversations on Economics, History & Geopolitics

• 2017 United States National Security Strategy

Other books references:

• A Sense of the Enemy: The High Stakes History of Reading Your Rival’s Mind by Zachery Shore

Articles:

• “The Danger of Trump’s Flamboyant Violence,” Jake Sullivan and Jon Finer, The New York Times, January 5, 2026.

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A NOTE FROM THE PRODUCER

Celine Rohr is the Deputy Editor for The Long Game

In this week’s episode of The Long Game, Jake Sullivan and Jon Finer sit down with the man who has spent more time negotiating with Iranian leaders than anyone: the architect of the Iran nuclear deal, former Secretary of State John Kerry.

They discuss the marathon diplomacy efforts that resulted in the JCPOA, Trump’s decision to strike Iran, the likelihood of a deal, prospects for a two state solution between Israel and Palestinians, and the future of the U.S.-Israel relationship. Secretary Kerry takes listeners inside the complex negotiations and explains why the final agreement entailed the “greatest insight, visibility, transparency, accountability of any agreement that I’ve ever seen since I’ve been in public life.”

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Recalling the coalition that came together, Kerry explains, “Of course, the IRGC would keep pushing, ‘You can’t negotiate with the Great Satan. There’s no way they would deliver. You can’t trust them,’ et cetera. And so I had this intermediary who was working the file in Oman, and I persuaded the Sultan to take a trip to Iran to meet with the Ayatollah in order to convey to him his sense that our bona fides were good, that we were prepared to be honest, we were prepared to be fair brokers. We were prepared to try to get a fair deal. And that played a role in his giving permission to these talks to even take place, because frankly they were bitter enough about the U.S. antipathy to them that it was really hard. There was no clarity of the fact that the Ayatollah was gonna let anybody really negotiate. In the end he became a force for closing the deal.”

Secretary Kerry also addresses criticisms of the JCPOA—including that its restrictions on Iran’s nuclear program were temporary and that it did little to rein in Iran’s regional proxy network—noting that it was always envisioned as a starting point, that diplomacy takes years of personal relationship-building and trust.

Then, Jake and Jon discuss Prime Minister Viktor Orban’s surprising defeat in Hungary’s election. Jon points out, “This is not some radical leftist who has defeated Victor Orban — he came out of the Orban movement. He is right wing on many of the same issues that Orban is right wing on….But in the vein of not letting the perfect be the enemy of the good here, there is actually a lot, I think, to be optimistic about in terms of how he will govern when it comes to Hungary’s role in Europe.”

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Plus, Orban’s loss bodes poorly for Trump’s relationship with the rest of Europe’s far right. Jake explains, “What’s been surprising to me is some of the other far right parties in Europe, like the AfD party in Germany, have actually started distancing themselves from the Trump administration, even before this, because they were recognizing that the bear hug from Trump, even for the voters they’re targeting, just doesn’t mean what they thought it might have meant a year ago. And it goes to show you how badly the Trump administration’s brand has cratered in Europe.”

Listen to the episode and as always comment below with your thoughts and questions or email Jake & Jon at longgame@voxmedia.com.

Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

• Joint Plan of Action (JPOA) — Iran Interim Nuclear Agreement (2013), Arms Control Association

• Prime Minister Benjamin Netanyahu’s Speech at Bar-Ilan University (2009), YouTube

• “Reckoning with Israel’s ‘One-State Reality,’” The Ezra Klein Show, New York Times, 4/14/26

• “You Know Who Believes in Climate Change? The Stock Market,” Mark Gongloff, Bloomberg, 11/6/25

• “The Clean Energy Revolution Is Unstoppable,” Eric Beinhocker and J. Doyne Farmer, Wall Street Journal, 2/28/25

• John Kerry Vietnam Veteran’s Hearing to Congress, Hawthorne High School

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A NOTE FROM THE PRODUCER

is the Lead Editorial Producer for The Long Game podcast

In this week’s episode of The Long Game, Jake Sullivan and Jon Finer react to President Trump’s announcement of a ceasefire between the United States and Iran. They assess who comes out ahead, what, if anything, the United States achieved from going to war, and what may have been lost in the process.

Jake and Jon walk through the chaotic lead-up to the announcement, including President Trump’s escalating rhetoric on social media, Pakistan’s role as an unlikely intermediary, and the sudden shift from brinkmanship to a two-week pause in fighting.

They make clear that any ceasefire is a good thing. As Jon puts it, “It is generally good news when a war ends and fewer people are going to be killed.” But they also stress how uncertain this moment is, with early violations and major gaps between the two sides.

A key focus is the Strait of Hormuz and what this war may have changed. Jake argues that Iran has demonstrated a powerful new form of leverage: “Iran has the capability to shut down the Strait of Hormuz… and that this is a source of deterrence.”

They also look ahead to what comes next from negotiations over shipping and Iran’s nuclear stockpile to whether this temporary pause can turn into something more lasting. Expectations for a breakthrough remain low, with Jon noting there is “a lot of contested space in the diplomacy.”

Stepping back, Jake raises the central question: “It’s not exactly clear… how you could make an argument that we’ve come out of this in a better place.”

At the end of the episode, Jake and Jon open up The Long Game mailbag for the first time, answering listener questions on the legality of targeted assassinations, what makes Russia a great power, what’s next for Cuba, and why they started the podcast after leaving the government.

Comment below or email Jake & Jon at longgame@voxmedia.com.

Follow The Long Game wherever you get your podcasts.

Transcript coming here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

“How Trump Took The U.S. to War With Iran,” Jonathan Swan and Maggie Haberman, The New York Times, 4/7/26.

Oren Cass X post reacting to President Trump’s recent threats

“Negative views of Israel, Netanyahu continue to rise among Americans – especially young people,” Pew Research Center, 4/7/26.

“A Whole Civilization Will Die Tonight,” Trump post on Truth Social, 4/7/26.

Threat Against Iran on Easter Sunday Trump post on Truth Social, 4/5/26.

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A NOTE FROM THE PRODUCER

Tamara Sepper is the Executive Producer for The Long Game

In this week’s episode of The Long Game, Jake Sullivan and Jon Finer go deep on President Trump’s prime-time address to the nation, his first formal speech on the Iran conflict more than a month after it began.

Jake frames the speech as “a tale of two speeches.” In the first three-quarters, Trump essentially declared the mission accomplished, a narrative that allows him to stop the war at any time. But toward the end of the speech, Trump threatened to bomb Iran “back to the stone age” and destroy its energy infrastructure if it doesn’t agree to a deal. Jake and Jon argue that the overall impression is of a president standing in a box, trying out different formulas to see which one sticks and essentially “market testing” how to end this war.

The conversation also covers the central question of what to do about Iran’s highly enriched uranium and the feasibility of a military operation to seize that material. They also address the administration’s core rationale for the war, articulated by Secretary of State Marco Rubio this week, that Iran was building a “conventional shield” of missiles and drones so powerful that no one could stop them from getting a nuclear weapon.

Jake and Jon then explore what a realistic path forward might look like and draw on their own experience negotiating with Iran during the Obama administration to explain how indirect diplomacy works (and doesn’t) and why the Iranian style of negotiation fundamentally clashes with Trump’s approach.

The episode culminates in a Red Team / Blue Team exercise in which Jake and Jon each take on the role of an Iranian advisor to the new Supreme Leader. Jon lays out the arguments for why Iran should take the deal and Jake makes the hardline case for continuing to fight.

Listen to the episode and as always comment below with your thoughts and questions or email Jake & Jon at longgame@voxmedia.com.

Read a transcript of this episode.

REFERENCES & SUPPLEMENTAL MATERIALS:

• President Trump Addresses Nation on War with Iran, CPAN, 4/1/26

• “Securing Iran’s enriched uranium by force would be risky and complex, experts say,” The Washington Post, 4/1/26.

• Rubio Reveals Why US Launched Preemptive Strike on Iran, YouTube, 4/1/26

• “Strait of Hormuz: Ships Paying Iran Yuan and Crypto Tolls For Safe Passage,” Bloomberg, 4/1/26.

• Joint Plan of Action (JPOA) — Iran Interim Nuclear Agreement (2013), Arms Control Association

• Iranian President’s letter to American people, X, 4/1/25

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A NOTE FROM THE PRODUCER

is the Lead Editorial Producer for The Long Game podcast

In this week’s episode of The Long Game, Jake Sullivan and Jon Finer are joined by Ruben Gallego, a Marine veteran, Iraq War combat survivor, and Senator representing Arizona, for a candid conversation about the war in Iran and the role of Congress in U.S. national security decision-making.

Gallego brings a perspective shaped by his experience fighting in one of the hardest-hit units of the Iraq War and losing his best friend in combat. That experience, he says, still defines how he sees decisions being made in Washington and the risks of repeating the same mistakes. His bottom line is simple, “The best way to support the troops is don’t send us to stupid wars.”

He argues that both parties of Congress have steadily ceded its authority over war to the executive branch resulting in fewer real constraints when the United States moves toward conflict. He also warns about the internal logic of escalation in a conflict like the Iran War. Once the U.S. is committed, each additional step can raise the stakes and narrow the exit path, a dynamic he describes as “chasing the dragon.” What begins as a limited operation can quickly evolve into something far more open-ended.

The conversation turns to the risks of putting ground troops in Iran and how new types of warfare in the form of drones and long-range strikes could make even limited operations far more dangerous than expected.

Jake and Jon reflect on the Obama administration’s decision to go to Congress for authorization to strike Syria after the Assad regime used chemical weapons and the lessons they took away from that experience.

Then they step back to assess the narrowing set of options facing President Trump, including seeking an off-ramp and further escalation. They discuss the role of public opinion, energy markets, and political pressure, as well as whether Congress will ultimately act to constrain the conflict.

Comment below or email Jake & Jon at longgame@voxmedia.com.

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Transcript here.

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

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A NOTE FROM THE PRODUCER

is the Lead Editorial Producer for The Long Game podcast

In this week’s episode of The Long Game, Jake Sullivan and Jon Finer are joined by Helima Croft, Head of Global Commodity Strategy at RBC Capital Markets and a former CIA Senior Economic Analyst, for a clear-eyed assessment of the global energy crisis triggered by the war in Iran.

Helima lays out the scale of the disruption including: the Strait of Hormuz effectively blocked, Qatari LNG exports offline, and large volumes of Middle Eastern oil unable to reach global markets. In her view, this is not just another geopolitical shock, it is the most severe energy disruption in decades, with no easy workaround.

Helima explains why markets failed to anticipate the risk, how the shale revolution reshaped expectations about supply shocks, and why oil prices may now be a lagging — not leading — indicator of geopolitical instability. The conversation also explores who is most exposed, from LNG-dependent economies in Asia and Europe to global supply chains already under strain.

Jake and Jon then step back to examine second-order effects across industries from petrochemicals and metals to semiconductors, including surprising choke points like helium, and what this crisis reveals about the fragility of the global economy.

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. Drawing on their experience in the White House Situation Room, they lay out three potential paths forward for the United States in the Iran War — each with significant risks and no clean resolution. It’s a look at what decision-making actually feels like at moments of crisis including constrained choices, imperfect information, and high stakes.

Comment below or email Jake & Jon at longgame@voxmedia.com.

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Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

“The US-Israeli strategy against Iran is working. Here is why,” Muhanad Seloom, Al Jazeera, 3/16/26.

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A NOTE FROM THE PRODUCER

is the Lead Editorial Producer for The Long Game podcast

In this week’s episode of The Long Game, Jake Sullivan and Jon Finer are joined by Danny (Dennis) Citrinowicz — senior researcher at the Institute for National Security Studies and former head of the Iran branch in Israeli Defense Intelligence — for a sober assessment of where the war with Iran stands following the killing of Supreme Leader Ali Khamenei.

Danny offers a blunt sitrep from Israel: what has been accomplished militarily, what remains unresolved, and why the strategic picture may be more complicated than it appears. In his view, decapitating Khamenei may have removed the very figure most responsible for keeping Iran from crossing the nuclear threshold, and could now push Tehran “beyond the Rubicon.” With Iran’s technical know-how intact and a stockpile of highly enriched uranium believed to be stored in tunnels under Isfahan, Danny argues the postwar reality may be an Iran more motivated — and better positioned — to pursue a bomb.

The conversation explores the emerging leadership dynamic in Iran, the resilience of the regime, and whether U.S. and Israeli objectives remain aligned as the conflict evolves. Jake and Jon press Danny on escalation risks, the role of regional actors, and what Washington misunderstands about Iran’s risk calculus..

In the final segment, Jake and Jon run a Red Team/Blue Team exercise on the most consequential unresolved question of the war: what to do about Iran’s enriched uranium stockpile in Isfahan. They game out a scenario in which President Trump considers sending forces in to secure or neutralize the material — a mission that could buy time against an Iranian sprint to a bomb, but also one that carries extraordinary operational, political, and escalation risks. It’s a debate about what “victory” actually means — and whether trying to put an exclamation point on this war could end up opening a new chapter of it.

Comment below or email Jake & Jon at longgame@voxmedia.com with your questions, comments, and recommendations.

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Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

Follow Danny (Dennis) Citrinowicz on X @citrinowicz

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Stay informed without hysteria, fear-mongering, or rage-baiting. Join our community for reasoned voices in unreasonable times.

A NOTE FROM THE PRODUCER

is the Lead Editorial Producer for The Long Game podcast

In this week’s episode of The Long Game, Jake Sullivan and Jon Finer are joined by Karim Sadjadpour to make sense of a rapidly unfolding crisis following the U.S.–Israel strikes that killed Iranian Supreme Leader Ayatollah Ali Khamenei and other senior leaders, Iran’s retaliation across the Middle East, and the profound uncertainty surrounding what comes next in the war.

Karim describes a conflict in which, so far, “everyone has been a loser” — the regime under pressure, Iranian society in shock, Israel facing incoming fire, Gulf states exposed, and no upside for Americans. But beyond the immediate exchanges of force lies a bigger question: what happens to a system built around a single dominant figure when that figure is suddenly gone?

The conversation explores Khamenei’s worldview — what made him resistant to compromise even under mounting pressure — and whether the Islamic Republic is more likely to fracture, harden, or evolve. Jake and Jon press on succession dynamics, the role of the Iranian Revolutionary Guard Corps, and what ordinary Iranians may be thinking as violence escalates. As Karim notes, in moments of instability, “it’s not the intellectuals and the poets that prevail… it’s men who are able and knowledgeable about mobilizing violence.”

In the final segment, Jake and Jon shift gears to a different national security confrontation taking place at home: the ongoing standoff between Anthropic and the U.S. Pentagon over the terms under which advanced AI models should be used for national defense. They unpack the Pentagon’s threats to label Anthropic a “supply chain risk,” the entry of OpenAI as a replacement government contractor, and what the dispute reveals about the evolving relationship between the U.S. government and private tech companies working on critical technologies.

With events moving quickly on both fronts, Jake and Jon take a moment to discuss what to watch in the days and weeks ahead — from Iran’s next move to how Washington handles its growing dependence on frontier AI.

Comment below or email Jake & Jon at longgame@voxmedia.com with your questions, comments, and recommendations.

Follow The Long Game on Apple, Spotify, or wherever you get your podcasts.

Transcript here.

REFERENCES AND SUPPLEMENTAL MATERIALS:

The Hedgehog and the Fox: An Essay on Tolstoy’s View of History, Isaiah Berlin

“The Iranian Hedgehog vs. the American Fox,” Karim Sadjadpour, The Atlantic, 1/31/26

“The Iranian Regime’s Existential Crisis—and What Might Come After Khamenei,” A Conversation With Karim Sadjadpour, Foreign Affairs, 2/28/26

“The Epic Miscalculations of Trump and Khamenei,” Karim Sadjadpour, The Atlantic, 2/28/26

“The Autumn of the Ayatollahs, What Kind of Change Is Coming to Iran?” Karim Sadjadpour, Foreign Affairs, Nov/Dec 2025

The U.S. and Israel launched a major set of strikes on Iran today and Iran has begun retaliating across the region. In a video message posted to Truth Social, President Trump described it as the start of “major combat operations.” Early reporting indicates the strikes hit Iranian military and security targets, and possibly senior leadership. Full confirmation and battle-damage assessment remains unclear. On Capitol Hill, the strikes have triggered an immediate war-powers fight over whether the action is authorized.

The Long Game hosts Jake Sullivan and Jon Finer went live on Substack to break it all down: what we know so far, what we don’t know yet, and the biggest questions that could 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?

Watch the video, and as always, please share your thoughts and questions in the comments. Or you can email us directly at LongGame@voxmedia.com. You can read a transcript of this discussion here.

Jake and Jon will continue to cover this developing story next week in a new episode of The Long Game, available wherever you get your podcasts.

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