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Just weeks after a high-stakes operation in Venezuela, the Trump administration is now setting its sights on Cuba. And this time… the stakes couldn’t be higher.
According to sources from the Wall Street Journal, U.S. officials are actively hunting for insiders within the Cuban government — officials who could cut a deal to remove the Communist regime… potentially by the end of 2026.
The focus is clear: Trump and his team see Cuba’s government as fragile, especially after losing their longtime ally, Venezuela’s Nicolas Maduro. The economic lifeline that Havana once had — heavily subsidized oil from Venezuela — has evaporated. Without it, Cuba’s economy is teetering on the edge of collapse.



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00:00Just weeks after a high-stakes operation in Venezuela, the Trump administration is now
00:21setting its sights on Cuba. And this time, the stakes couldn't be higher. According to sources
00:27from the Wall Street Journal, U.S. officials are actively hunting for insiders within the Cuban
00:32government, officials who could cut a deal to remove the communist regime, potentially by the
00:38end of 2026. Well, Cuba's in bad shape. Cuba relied on Venezuela for oil and for money.
00:46And nobody really knows what's going to happen with Cuba. They're doing very poorly. They're really
00:51a third world all the way. And we have a lot of great Cuban Americans. And I would say Marco fits
00:57very solidly into that category. And I might ask you to say a few words about we were discussing it
01:03before. Cuba is a very different. They don't have energy. They don't have oil, but they would
01:07live off of the oil from Venezuela. And what they do have is very strong people and very powerful
01:15people militarily. And they would protect the people running Venezuela. And they would take
01:22in a lot of money from Venezuela. And now they don't have that. They won't be taking in any money. So,
01:27Marco, what do you think? Well, I mean, the fundamental problem in Cuba is that it's run
01:30by incompetent people that don't know what an economy looks like, much less a functioning one.
01:34They've made a choice. And that is, they would rather have political control over the people than they
01:38would have an economy that functions. And they've gotten away with it for 60-something years,
01:42because they've had donors, the Soviet Union, and now most recently Venezuela. But that's now gone.
01:47So the people in control in Cuba have a choice to make. They can either have a real country with a
01:51real economy where their people can prosper, or they can continue with their failing dictatorship
01:56that's going to lead to systemic and societal collapse. That's a very stark and dramatic choice,
02:00and it's one we hope to make the right one. We don't have an interest in a destabilized Cuba,
02:04but that would be their fault because they refuse to allow the people of Cuba to have
02:08either economic or political freedom for that matter. The focus is clear. Trump and his team
02:14see Cuba's government as fragile, especially after losing their longtime ally, Venezuela's
02:19Nicolas Maduro. The economic lifeline that Havana once had, heavily subsidized oil from Venezuela,
02:26has evaporated. Without it, Cuba's economy is teetering on the edge of collapse.
02:31The White House's strategy is multi-pronged. It includes cutting off remaining oil supplies,
02:37targeting Cuba's overseas medical missions, a major source of hard currency,
02:42sending a clear signal to regime insiders that cooperation could spare them, but resistance will
02:48not be tolerated. And the message from Trump couldn't be clearer. On January 11th, he wrote on
02:55Truth Social, in his signature all-cap style, there will be no more oil or money going to Cuba,
03:02zero. I strongly suggest they make a deal before it is too late.
03:07You mentioned Cuba yesterday in his remarks. Does the U.S. have a plan to do something?
03:12Well, Cuba always survived because of Venezuela. Now they won't have that money coming in. They
03:18won't have the income coming in. You know, a lot of Cubans were killed yesterday. You know that.
03:24A lot of Cubans were killed.
03:26The bodyguards. No, they're looking. There was a lot of death on the other side. No death on our side.
03:34Even though no public military action has been announced against Cuba yet, several Trump allies
03:39believe the communist regime could face a Venezuela-style shakeup. But experts cautioned that
03:45removing the government could trigger a serious humanitarian crisis. After all, Cuba has resisted
03:51U.S. pressure for decades, and insiders willing to cooperate may be few and far between.
03:56Let's break down why this is such a big deal.
04:00Cuba has depended on Venezuela for oil since 1999, when Chavez took power. That supply kept the Cuban
04:07economy afloat. With Maduro ousted and Venezuela's economy destabilized, Havana now faces a supply crunch
04:14that could bring the nation to its knees in a matter of weeks if U.S. sanctions and restrictions
04:19are fully enforced. The U.S. government is also going after one of Cuba's most important sources
04:25of revenue, its overseas medical missions. Visa restrictions are being imposed on Cuban and
04:30foreign officials involved in these programs, further tightening economic pressure. And this comes on the
04:36heels of the Venezuela operation, a playbook Trump apparently hopes to replicate. Officials see the
04:42Maduro mission as both a warning and a template for how to deal with Havana. Despite the looming threats,
04:48insiders say Cuba is a much tougher nut to crack. As former Obama administration official Ricardo
04:54Zunaga explained, the Cuban government is unlikely to have officials willing to turn on their own people,
05:00even under extreme pressure. And it's not just Cuba in Trump's crosshairs. Iran is facing a far more
05:07direct threat as protests continue. Trump recently warned that if unrest persists, the whole country
05:13is going to be blown up. Clearly, 2026 is shaping up to be a year of intense U.S. foreign policy moves
05:20in multiple regions. So here's the million-dollar question. Can Cuba withstand this growing pressure,
05:27or is a Venezuela-style regime change looming on the horizon?
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