How Far Will Trump Go in Cuba?

March 31, 2026·1 hr 7 min·5 clips

Cuba's electrical grid is collapsing under its own weight, depleting families' frozen food stockpiles and triggering historic protests.

The opening is packed with ads. Once the roundtable starts, Jonah Goldberg, filling in for Steve Hayes, uses Cuba's nationwide blackouts as the pressure point. The question quickly widens. He ties the outages to the ruling Communist Party's future and to the chance that Cuba could become a target of Trump's foreign policy. Gil Guerra is the specialist voice. His Dispatch explainer, titled "Will Cuba Be the Next to Fall?", gives the panel its frame. Kevin Williamson and Megan McArdle join the conversation. The excerpt is more interested in leverage, pressure, and adversary reaction than in clean action talk. Cuba understands the pressure. So, the argument goes, do foreign adversaries that do not want the United States to have usable leverage over Cuba. Russia is the example that makes it concrete. Its current oil deliveries to Cuba, described as moving around the embargo, are treated as outside support working against that leverage. Military action stays conditional. The panel does not sell it as inevitable. The visible claim is that outside support, Cuban calculations, and American leverage would all affect whether force is used. The tone stays dry, with a joke about foppish playboys and Donald Trump landing as a quick comic beat. Then the clip moves back to ads. The editorial material sits between a sponsor packed opening and another sponsor break. The closing excerpt is promotional and leaves Cuba behind for Kansas health messaging.

As heard by us

A focused Dispatch roundtable on Cuba's blackouts, regime pressure, Russian oil, and Trump's possible foreign-policy next move.

Jonah Goldberg steers a Dispatch roundtable on Cuba's nationwide blackouts, the future of its ruling Communist Party, and whether the Trump administration might put the island next in its foreign-policy sights.

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Why you'd press play

For a sober read on Cuba's blackouts, the ruling party's future, and whether the island is next in Trump's crosshairs.

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