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.

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Watch the video of this episode on YouTube.

Show notes are available here.

Transcript available here.

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The Long Game is produced by the Vox Media Podcast Network.
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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.

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Watch the video of this episode on YouTube.

For show notes and transcripts, find and follow us on Substack.

Email Jake and Jon at [email protected].

The Long Game is produced by the Vox Media Podcast Network.

Photo credit: Photographer: Alex Brandon/AP Photo/Bloomberg via Getty Images
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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 [email protected].

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
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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 [email protected].

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 [email protected]. Or leave a comment below. 

The Long Game is produced by the Vox Media Podcast Network.
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