The Long Game with Jake Sullivan and Jon Finer

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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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 [email protected]. 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 [email protected]. 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 [email protected]. 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 [email protected]. Or leave a comment below.
Learn more about your ad choices. Visit podcastchoices.com/adchoices