January 23rd, 2026: Inside the White House Plan to Topple Cuba’s Communist Government & Sanctions Enforcement Escalates
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What is the main topic discussed in this episode?
It's Friday, the 23rd of January. Welcome to the President's Daily Brief. I'm Mike Baker, your eyes and ears on the world stage. All right, let's get briefed. First up, a new report is giving us an inside look at the White House's efforts to engineer regime change in Cuba, with U.S. officials emboldened by events in Venezuela and actively hunting for Cuban power brokers willing to cut a deal. Later in the show, President Trump meets with Ukrainian President Zelensky in Davos with Kiev, saying security guarantees are settled. But the most critical issue of all, and that would be territory, well, that issue remains unresolved. Plus, the war against Russia's shadow fleet is expanding, as France's navy – and yes, they do have one, and it's quite good, actually – intercepts an oil tanker in the Mediterranean, linked to Moscow's covert sanctions-busting network.
And in today's Back of the Brief, we turn again to Iran, where a young Iranian soldier has been sentenced to death for refusing orders to fire on protesters during the nationwide anti-regime demonstrations. But first, today's PDB Spotlight. A new report says the White House is actively seeking to overthrow Cuba's communist government, potentially by the end of the year. And look at that. What's old is new again. According to reporting from the Wall Street Journal, the Trump administration believes Cuba's regime is more fragile than at any point in the past seven decades. U.S. intelligence assessments describe an economy on the brink, chronic shortages of food and medicine, rolling blackouts, and a growing sense of desperation across the island.
And maybe, perhaps most critically, Havana has now lost its most important lifeline. That would be subsidized oil from Venezuela, following, of course, the U.S.-backed operation earlier this month that removed President Nicolas Maduro from office. And administration officials see what happened in Caracas not just as a one-off success. but as a blueprint for Cuba. According to officials familiar with the planning, the strategy is not a traditional invasion or a Cold War-style coup.
What are the White House's plans for regime change in Cuba?
Instead, Washington is applying intense pressure on the regime while quietly searching for Cuban government insiders who might be willing to cut a deal once it becomes clear that the current system can't survive. President Trump himself has publicly amplified that message, warning Havana that there will be no more oil or money and urging Cuban leaders to make a deal before it's too late. Now, to understand why U.S. officials think this might work, you have to look back at how the Venezuelan operation unfolded. New reporting from The Guardian reveals that the Maduro capture was preceded by months of secret back-channel discussions with senior figures inside the Venezuelan regime, most notably Delcy Rodriguez, the then vice president and now the country's acting president.
According to multiple sources, Rodriguez and her brother, the propaganda minister, quietly assured U.S. officials that they would cooperate once Maduro was gone. These regime figures did not agree to overthrow Maduro themselves. Instead, they signaled that they would help manage the aftermath, keeping the state functioning, avoiding civil war, and preventing Venezuela from collapsing into chaos. That assurance helped persuade even hardliners inside the Trump administration that working with regime insiders was preferable to potentially unleashing a failed state on America's doorstep. The result was a targeted operation that removed the leader while leaving much of the system intact. Venezuela did not descend into mass violence.
Oil talks resumed, deportation flights continued, political prisoner negotiations began. From Washington's perspective, it was a transactional success. Now, reportedly, that same logic is being applied to Cuba.
What security guarantees were discussed between Trump and Zelensky?
Administration officials believe the island's dependence on Venezuelan oil has left it uniquely vulnerable. Economists warn Cuba could run out of fuel within weeks, bringing transportation, electricity and basic services to a halt.
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Chapters
6 chapters
1
What is the main topic discussed in this episode?
0:12–2:25
2
What are the White House's plans for regime change in Cuba?
2:25–4:13
3
What security guarantees were discussed between Trump and Zelensky?
4:13–5:37
4
How is France addressing Russia's shadow fleet in the Mediterranean?
5:37–6:49
5
What recent events highlight the situation in Iran regarding protests?
6:49–7:55
6
How is the U.S. applying pressure on Cuba's communist regime?
7:55–24:03
Speakers
2 identifiedMore from The President's Daily Brief
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