President Donald Trump sat down with Fox News correspondent Trey Yingst and casually hinted that some pretty significant things are brewing regarding Cuba. As Trending Politics reported, the president offered a two month window for developments while being characteristically vague about what those developments might actually look like.
"A lot of things are going to happen in Cuba over the next maybe two months, but I don't see it being like Venezuela," Trump said. When Yingst followed up with the single word question that probably made a few Pentagon officials choke on their coffee, "Militarily?", Trump responded with the kind of answer that neither confirms nor denies anything while somehow doing both: "Venezuela has massive amounts of oil. We could do that with Cuba, it would not be hard for us to do."
So to recap: he said it would not be like Venezuela, was asked if he meant military action, and then immediately started talking about how easy it would be to do what they did in Venezuela. Classic negotiating technique or just a guy thinking out loud? You decide.
The comments come during what has been a full court press on the Cuban government. Since early 2026, the Trump administration has been running a maximum pressure campaign that reads like a checklist titled "Ways To Make A Country's Week Worse." After the January removal of Venezuelan leader Nicolas Maduro, the U.S. effectively cut off Cuba's subsidized oil shipments from Venezuela, causing massive fuel shortages on the island. Because when your main gas station closes, things get rough.
Last month, the administration slapped sanctions directly on Cuban President Miguel Diaz-Canel, his wife Lis Cuesta Peraza, and Colonel Alejandro Castro Espin. They also went after CUPET, the state oil enterprise, which is a bit like sanctioning a lemonade stand that already ran out of lemons.
Then there was the move to unseal federal charges against longtime dictator Raul Castro in connection with the 1996 downing of civilian aircraft. That one had been sitting in a drawer for three decades apparently waiting for the right moment.
On the diplomatic side, CIA Director John Ratcliffe visited Havana back in May to deliver what amounts to a polite ultimatum: the United States will engage seriously on economic and security issues, but only if Cuba makes fundamental changes. Discussions reportedly covered intelligence cooperation, economic stability, and the general understanding that Cuba should not be hosting activities by U.S. adversaries in the Western Hemisphere.
The administration has also deployed a carrier group to the Caribbean, because nothing says "let's talk diplomacy" quite like parking an aircraft carrier in someone's general vicinity.
Whether those "things" Trump referenced turn out to be military, economic, diplomatic, or some combination remains to be seen. The two month clock is ticking, and Cuba is presumably not sleeping well.
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