The Long Game Podcast
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Trump Is Running Out of Options on Iran
Posted
May 28, 2026
Views
21,808
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447
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2.58%
May 28, 2026
21,808
447
116
2.58%
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1:07:43Now PlayingTrump's Iran war reaches a Groundhog Day stalemate while former Obama Cuba negotiator Ricardo Zuniga warns that Trump's maximum pressure campaign against Havana, the Raul Castro indictment, and escalating U.S. surveillance flights are setting the table for a military strike on Cuba that won't deliver the regime change victory Trump is looking for.
As negotiations with Iran are underway, Jake Sullivan and Jon Finer walk through a full options memo for President Trump — from walking away with no deal, to a JCPOA-style nuclear agreement Trump swore he'd never accept, to returning to military strikes that already failed once. With the Strait of Hormuz still closed, Iran's enriched uranium stockpile unresolved, and U.S. military readiness being drained, they argue the endgame was always a deal similar to the one Obama made.
Then, they turn to Trump's Cuba invasion threat. Former NSC official Ricardo Zuniga, the architect of Obama's secret Cuba normalization talks, joins to break down why Cuba won't fold like Venezuela, what Trump actually wants from Havana, and why a U.S. military strike on Cuba is more likely than most people think.
Topics covered:
- The politics of U.S. Cuba policy
- What Obama was trying to achieve through engagement with Havana
- How the secret U.S.-Cuba negotiations actually worked
- Trump’s hardline posture toward Cuba
- Whether Cuba actually poses a threat to the United States
- Why Zúñiga thinks the current pressure campaign could lead to a protracted crisis or even military action
- A deep dive into Cuba, Iran, U.S. diplomacy, sanctions, military pressure, Latin America, Venezuela, Trump foreign policy, and the future of American power.
Photo credits:
Trump cabinet meeting at the White House in Washington, D.C., on May 27, 2026. Photographer: Samuel Corum/Sipa/Bloomberg via Getty Images
Cuba's President Raul Castro, right, and U.S. President Barack Obama, left, attend a press conference at the Revolution Palace in Havana on March 21, 2016. Xinhua/Joaquin Hernandez via Getty Images
Cuba's President Miguel Diaz-Canel waves a national flag during celebrations marking the victory on the 65th anniversary of the Bay of Pigs invasion, April 16, 2026. Photo by ADALBERTO ROQUE / AFP via Getty Images
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#Iran #Cuba #Trump #MiddleEast #USForeignPolicy #IranWar #Diplomacy #LatinAmerica #MarcoRubio #Venezuela #JakeSullivan #JonFiner #TheLongGame #NationalSecurity #Geopolitics #ForeignPolicy #USPolitics #IranDeal #CubaPolicy #AbrahamAccords
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