Foreign Office by Michael Weiss

Foreign Office by Michael Weiss

The Cuba Crabwalk

An attempt to explain the Trump administration’s chaotic strategy in the Caribbean

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Foreign Office by M.Weiss
May 19, 2026
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On May 14, CIA Director John Ratcliffe paid a visit to the Cuban regime in Havana. CIA on X.

“Cuba is next,” Donald Trump declared at a gathering of investors in Miami in March, and his administration has certainly behaved accordingly since.

The last two weeks alone have hinted at a strong possibility of Washington taking decisive action to put an end to the Castroist nuisance 90 miles off the coast of Florida, either through a softening of its sclerotic regime or by a forced change in leadership. The question is how it aims to do this: with economic pressure and coercive diplomacy, or with warplanes and Bay of Pigs 2: Electric Boogaloo?

In trying to suss out aggressive foreign policy designs in an administration as chaotic and mercurial as this one, it often pays to work your way backward from the sensationalist to the prosaic disclosures.

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