The Long Game with Jake Sullivan and Jon Finer

Jake Sullivan and Jon Finer unpack Trump’s Greenland gambit and the strain it has placed on NATO and America’s closest partners. They situate the crisis within a one-year assessment of Trump’s foreign policy and debate whether pressure and tariffs are advancing U.S. interests — or undermining the alliance system that has long underpinned American power.

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Show notes and a transcript of the episode are available here.

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Email Jake and Jon with your thoughts and questions at [email protected]. Or leave a comment below. 

Transcript here, coming soon. 

Note: This episode was taped early afternoon on Wednesday, January 21, prior to Trump’s announcement of reaching a framework deal with NATO Secretary General Rutte.

The Long Game is produced by the Vox Media Podcast Network.
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Jake Sullivan and Jon Finer examine the rapidly unfolding crisis in Iran, from nationwide protests and an information blackout to the regime’s brutal crackdown. They place the moment in historical context and debate the central question now facing Washington: whether U.S. military action would protect protesters — or risk escalation without changing realities on the ground.

Follow The Long Game so you never miss an episode. New episodes drop on Fridays.

Show notes and a transcript of the episode are available here.

Watch the video of this episode on Youtube.

Join us on Substack

Email Jake and Jon with your thoughts and questions at [email protected]. Or leave a comment below. 

Transcript here, coming soon. 

The Long Game is produced by the Vox Media Podcast Network.
Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode, Jake Sullivan and Jon Finer discuss the U.S. special operations raid that captured Nicolás Maduro and the Trump administration’s claim that the U.S. will now “run” Venezuela.  Drawing on their experience in the White House, they assess the operational risks of the capture, unclear end state, and the limits of the promised economic upside. The conversation widens to Greenland and what the administration’s refusal to rule out force could mean for U.S. power and global stability.

Follow The Long Game so you never miss an episode. New episodes drop on Fridays.

Show notes and a transcript of the episode are available here.

Watch the video of this episode on Youtube.

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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In this episode, Jake Sullivan and Jon Finer cover:

- The fast-escalating U.S. pressure campaign against the Maduro regime in Venezuela — including the growing American military buildup and Trump’s post calling Venezuela a “foreign terrorist organization.”

- President Trump’s decision to allow the sale of Nvidia’s advanced H200 AI chips to China — announced on the same day that the DOJ called the chip a cornerstone of “AI superiority.”

- A Red Team/Blue Team exercise on the U.S.-backed peace proposal for the Ukraine–Russia war, with Jake and Jon stepping into the roles of advisers to Zelensky and Putin.

Follow The Long Game so you never miss an episode. New episodes drop on Fridays.

Show notes and a transcript of the episode are available here.

Watch the video of this episode on Youtube.

REFERENCES & SUPPLEMENTAL MATERIALS: 

- Interview with Christopher Fouqet “Bloomberg Talks: Christophe Fouqet,” December 12, 2025.

“U.S. authorities shut down major China-linked AI tech smuggling network,” Department of Justice Press Release, December 8, 2025.
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In this episode, Jake Sullivan and Jon Finer cover:

- The U.S. “double tap” strike on a boat in the Caribbean that reportedly killed two survivors, raising questions about potential war crimes, and Congress’s response

- Trump’s newly released 2025 National Security Strategy

- The Trump Administration’s decision to greenlight the sale to China of Nvidia’s powerful H200 chips used in AI 

Then, a lightning round of questions for each other.

Follow The Long Game so you never miss an episode. New episodes drop on Fridays.

Show notes and a transcript of the episode are available here.

Watch the video of this episode on Youtube.

Join us on Substack

Email Jake and Jon with your thoughts and questions at [email protected]. Or leave a comment below. 

Transcript here, coming soon. 

The Long Game is produced by the Vox Media Podcast Network.
Learn more about your ad choices. Visit podcastchoices.com/adchoices