What Iran war? In desperate search of a legacy, Trump goes after Cuba’s failing regime. It's sad on both sides
commentary
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
Amid Iran war, peace talks and chaos, Trump eyes Cuba 'collapse' | What we know
Trump’s Cuba strategy echoes his Venezuela playbook. But there are key differences
‘Rabbit holes all over the place’: How hard it would be for Trump to rebuild Cuba
Trump's Cuba strategy echoes his Venezuela playbook. But there are key differences
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
The “Venezuela Option” would address only a portion of the issues that have hobbled the country and driven the conflict with the…
Analysis: Any move towards yet more action by the stretched US forces would come with high risks.
The fallout from the Iran conflict and the approaching U.S. midterms may change Trump’s calculations.
If the US does take military action the consequences are highly uncertain
