Politics5/21/2026•CNN

Analysis: Trump seeks redemption in Cuba after his regime-change failure in Iran | CNN Politics

Analysis: Trump seeks redemption in Cuba after his regime-change failure in Iran | CNN Politics

President Donald Trump is chasing the kind of regime-altering triumph in Cuba that has eluded him in Iran. But any move toward yet more action by the stretched US armed forces would come with high political and military risks. The US government’s indictment of 94-year-old former Cuban President Raúl Castro for murder and conspiracy to kill US nationals is a remarkable twist in a nearly 70-year American showdown with the communist island. Wednesday’s indictment — which came on Cuban Independence Day — is also a significant step up Trump’s escalation ladder. It coincides with a US oil blockade that has caused a grave humanitarian crisis and threatens to collapse Cuban society; steadily rising diplomatic pressure; and a recent list of demands delivered in Havana by CIA Director John Ratcliffe. Trump has been threatening Cuba for weeks, saying he can do “anything” he wants with the impoverished state and may have “the honor of taking Cuba.” On Wednesday, he said he was “freeing up” the country. “It’s a failing nation. You see that. It’s falling apart. They have no oil, they have no money,” Trump told reporters. “But we’re there to help — we’re the

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