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

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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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