The Long Game with Jake Sullivan and Jon Finer

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.

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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.
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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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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 [email protected]. Or leave a comment below. 

The Long Game is produced by the Vox Media Podcast Network.
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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 [email protected]. Or leave a comment below. 

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

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