Is Cuba Next?

For the first time in nearly 70 years, it looks like there may be major political changes afoot in Cuba — driven by the United States. The Trump administration has been ratcheting up pressure on the island, including by imposing an oil embargo that is strangling the country's energy supplies. On Monday, March 16, Cuba experienced a complete collapse of its electric grid, triggering a nationwide blackout. Meanwhile, Cuba's erstwhile major patron was Venezuela, which, since the ouster of Maduro, no longer provides the support on which Havana once relied. Recent reporting also indicates that Washington and Havana are now engaged in direct talks, even as the Trump administration is explicitly seeking the ouster of President Miguel Díaz-Canel. Trump has also publicly suggested he could "take" Cuba. So will Cuba go the way of Venezuela? What role does the U.S. war in Iran play in Washington's policy toward Cuba? And might the Cuban regime survive after all? My interview guest today, James Bosworth, answers these questions and more. He writes the Latin America Risk Report on Substack, and we kick off with a brief overview of seven decades of U.S.-Cuba relations before having a longer conversation about where things stand today — and where they may be headed.

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Is Cuba Next? is an episode from Global Dispatches -- Conversations on Foreign Policy and World Affairs by Global Dispatches.

This episode is 26:37 long.

This episode was published on Mar 23, 2026.

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