March 15, 2026
Trump’s Cuba strategy is straightforward. The outcome will be anything but.
Even as the war in Iran remains in full swing, Trump is already eying his next target: Cuba.
Washington’s oldest adversary in the Western hemisphere is in the midst of an economic and social crisis the likes of which the Cuban Communist Party hasn’t confronted since the 1990s. That’s when the collapse of its former patron, the Soviet Union, forced the island to make do with a lot less. The Trump administration’s Cuba policy is only exacerbating those fissures.
The strategy is straightforward: place so much financial pressure on the Cuban government that it has no option but to meet Trump’s demands, like opening up the country to a multi-party democracy. Trump’s Jan. 29 executive order slapping any country that transports or exports fuel to Cuba with tariffs, combined with a new U.S. Justice Department initiative that seeks to indict senior Cuban officials, is meant to provide Trump with even more leverage in the ongoing talks with Havana.
Trump seems confident he can do to Cuba what he did to Venezuela more than two months ago—decapitate the senior leadership, work with more pragmatic underlings and bring a former U.S. adversary into Washington’s orbit.
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