What Iran war? In desperate search of a legacy, Trump goes after Cuba’s failing regime. It's sad on both sides
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What Iran war? In desperate search of a legacy, Trump goes after Cuba’s failing regime. It's sad on both sides
Executive Editor
Published
May 24, 2026 9:00AM (EDT)
Analysis: Trump seeks redemption in Cuba after his regime-change failure in Iran | CNN Politics
Trump has Cuba in his gunsights. His next move could define his legacy
Trump seeks redemption in Cuba after his regime-change failure in Iran
The Irish Times view on Cuba: in Trump’s sights
Trump's Cuba strategy echoes his Venezuela playbook, but experts point out key differences
Trump eyes Cuba as possible military victory as Iran talks stall
Trump’s Cuba strategy echoes his Venezuela playbook. But there are key differences
Trump's Cuba strategy echoes his Venezuela playbook. But there are key differences
4 ways Trump is following the Venezuela playbook with Cuba, and one where he isn't | Fortune
Donald Trump is pushing towards the end game in Cuba
President Donald Trump is chasing the kind of regime-altering triumph in Cuba that has eluded him in Iran. But any move toward…
The US President wants to be the one who finally removes a long-standing American enemy
Analysis: Any move towards yet more action by the stretched US forces would come with high risks.
If the US does take military action the consequences are highly uncertain
Similar pressure campaigns do not equal similar results, experts say, even if President Donald Trump has often warned that "Cuba…
The Trump administration has ratcheted up its pressure campaign on Cuba as talks with Iran have still not resulted in a…
