The Long Game with Jake Sullivan and Jon Finer

President Trump is simultaneously pursuing peace talks with Iran while escalating U.S. military pressure in the region following recent strikes. Jake Sullivan and Jon Finer revisit the policy options most likely facing the administration and walk through how they would advise the president at this moment of escalation and diplomacy.

Then, 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, joins to discuss:


The politics behind U.S.-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


The likelihood that the U.S. will undertake some form of military action in Cuba


Whether sanctions and pressure campaigns still create meaningful leverage


How Venezuela reshaped U.S. thinking about authoritarian regimes in the hemisphere

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

Watch the video version of this episode on YouTube.

Show notes are available here.

Transcript coming soon.

Email Jake and Jon at [email protected].

The Long Game is produced by the Vox Media Podcast Network.
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President Trump is preparing to sign a major executive order on AI and cybersecurity at a moment of growing concern over cyber threats from China, Russia, Iran, and criminal ransomware gangs.

Jen Easterly, former Director of the Cybersecurity and Infrastructure Security Agency and now CEO of RSAC, the world's largest cybersecurity community, joins Jake Sullivan and Jon Finer to discuss:


Why America has a software security problem, not just a cybersecurity problem


How insecure software shifted risk from tech companies onto consumers


Why AI tools like Mythos and GPT-5.5 Cyber could fundamentally change cyber defense


What China’s Volt Typhoon campaign revealed about U.S. infrastructure vulnerabilities


How cyber warfare has shaped conflicts in Ukraine and Iran

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

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

Watch the video version of this episode on YouTube.

Show notes are available here.

Transcript coming soon.

Email Jake and Jon at [email protected].

The Long Game is produced by the Vox Media Podcast Network.
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President Trump heads to Beijing for a high-stakes summit with Xi Jinping at a moment of growing instability in the Middle East and rising anxiety across Asia.

In this episode, former U.S. Deputy Secretary of State Kurt Campbell joins Jake Sullivan and Jon Finer to preview the summit and discuss:


Why China increasingly believes the United States is in decline


Xi Jinping’s read of Donald Trump


Whether Trump might shift U.S. policy on Taiwan or semiconductor export controls


How the Iran war is factoring into  China’s strategy 


What comes next in the U.S.-China competition

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

Watch the video version of this episode on YouTube.

Transcript here.

Email Jake and Jon at [email protected].

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

REFERENCES & SUPPLEMENTAL MATERIALS:

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

"The Stakes of Trump vs. Xi," Kurt Campbell, Foreign Affairs, May 2026.

“Xi Is Planning for China’s Final Victory Over the U.S.,” The New York Times, Julian Gerwirtz, May 13, 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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Iran war developments, including new signs of a potential deal, UAE’s withdrawal from OPEC, and what weeks of conflict have revealed about U.S. leverage.

In this episode, Jake Sullivan and Jon Finer discuss:

- Why a deal with Iran may be inevitable but harder to reach now

- How markets, military risks, and politics are shaping Trump’s strategy

- Warnings about depleted U.S. munitions 

- Why the UAE is leaving OPEC and what it says about tensions with Saudi Arabia

- A Red Team/Blue Team debate on in U.S. reducing troops in Europe

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 available here.

Email Jake and Jon at [email protected].

The Long Game is produced by the Vox Media Podcast Network.
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Dan Wang, author of Breakneck, breaks down the divide between China’s “engineering state” and America’s “lawyerly society” and what that means for the future of U.S.-China competition.

Wang joined Jake and Jon before a live audience at the Endless Frontiers conference in Austin, Texas.

In this episode:

- Why China builds at scale and why the U.S. often struggles to keep up

- The strengths and limits of China’s model, from manufacturing to social policy

- A closer look at Xi Jinping’s leadership and decision-making

- Why “process knowledge” is key to rebuilding American capacity

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 coming soon.

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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