Trump is likely to succeed on his Cuba policy
By the end of the year, it's possible Cuba's government will be more "Delcy-like" than Venezuela's.
By the end of 2026, the most likely scenario is that Cuba’s regime becomes “Delcy-like1” in terms of its willingness to welcome and work with the Trump administration. While being a bit vague about the exact resolution criteria, I’d say this sort of shift is about 80% likely. The country will be more open to US investment. Bilateral trade will increase. The US will help Cuba with its energy infrastructure. It’s quite likely that by the first half of 2027, if not sooner, embassies will have reopened in both countries. Cuba will effectively become a client state for the United States. And the US, somewhat ironically and contradictorily, will become the next “black knight” that helps Cuba evade and survive the economic pressure of US sanctions.
For decades, US policy has been to overthrow the Cuban dictatorship, with occasional efforts at detente. Trump is working to overturn that dynamic, working from inside the Republican Party with a Cuban-American politician leading his global diplomacy in order to cut a deal with the dictatorship that breaks the political impasse in the US. That means this is not regime change nor democratization. This should not require “boots on the ground” operations or a military extraction mission like the one in Caracas in January.
Trump will portray this shift on Cuba as a massive foreign policy win. He will claim to have done what no president has been able to do since the 1950s. Comparisons to Obama’s attending a baseball game with Raul Castro won’t stick because Obama tried to treat Cuba as a fellow nation-state, not a client state like Trump. Comparisons to how the US managed the Batistas and the other Cuban organized crime leaders from the pre-revolutionary era may be more apt, but will be seen as whining from those who failed in the past.
Ultimately, this shift in US policy is why Trump “succeeds” where others have failed. Many other presidents (except Obama and Biden) worked toward some sort of regime change in Cuba. Trump is the first president to accept the dictatorial regime as long as they behave differently toward the US. While Cuba does not have the geopolitical significance of Venezuela, Panama or Greenland, it’s an easy, symbolic win and one that has the potential for nice tourist resorts, something Trump really cares about.
Most sanctions and the embargo will remain in place, with licenses and workarounds. Those policies give Trump the ability to influence Cuba’s economy and have leverage over its political leadership and any businesses that wish to invest in the country. He can use those policies to restrict certain influence of China and Europe (though he will want their money flowing into Cuba in some way) and prefer US companies that can profit from the arrangement. The state sponsor of terrorism designation will likely need to be dropped because the laws governing it work differently, but many of the other current trade restrictions will remain in place as a threat and a form of control.
This policy may not be sustainable in the long term. But it’ll last at least a few years, probably through the end of the Trump administration, handing a real challenge to the next US president.
Does Diaz-Canel leave power? Probably. Getting rid of Diaz-Canel is far less important in Cuba than removing Maduro in Venezuela. I think Cuba’s leader, like many in the corrupt regime, would be willing to cut a deal that keeps him in place. That said, Trump has a “kingpin theory of power” in which the top person always matters. So for Trump, removing the top guy in Cuba is important in reality as well as symbolically. It gives him some limited political space in the US, demonstrating to those that care (Florida politics!) that some change has occurred. The change at the top also provides some legal wiggle room as well, potentially allowing him greater leeway to interpret the various restrictions on Cuba trade and investment that allow him to work around the Congress-imposed restrictions meant to prevent a US president from working with the Cuban dictatorship.
Trump’s planned Cuba policy does not require a specific Delcy-like figure to fill in as leader, though someone will be portrayed that way. Many in Cuba’s military leadership are so corrupt and transactional, the ideology of the Castro-led revolution so far gone, that the entire system is more amenable to US takeover than Venezuela, where Rodriguez is balancing stakeholders who are less eager to follow the pro-US path that she is on. For years, Cuba’s opposition criticized the military as corrupt, viewing it as a reason for it to be toppled. Trump, instead, views the corruption as an opportunity for leverage. Those who don’t go along with the negotiated accommodation will be killed, imprisoned, or exiled, one of the advantages of Cuba being a dictatorship.
What are the risks?
Cuba’s physical infrastructure, particularly the energy grid, is so far gone that there is significant suffering on the island for years to come. This means that the US could end up being “in charge” of a Cuba that is falling apart.
The Cuban people want freedom and protest. While Cuba’s regime is good at repression, the politics of repression become quite different once they are a client state of the US. It may not be as simple.
GAESA’s economic and political influence is so vast that Trump will need to find a way to co-opt it and deal with any economic actors who try to resist or compete. In other words, as Cuba’s leadership becomes like Delcy, there will be a few Alex Saabs to be removed.
Havana is more eager to accept this deal than Miami. It’s possible (though not likely) that the Cuban-American population and Cuban migrant community recognize the lack of democratic change and turn against Trump and Rubio.
On that last point, the role of Rubio becomes important. He is the person who provides Trump the credibility necessary within the Republican Party and Florida politics to make this change work within the US political system. But why would Rubio give up his dream of a democratic Cuba to accept this sort of compromise? I’m sure that Rubio views this as a step in the direction of eventual change, and, as with Venezuela, he will try to sell the accommodation of the Cuban dictatorship as a temporary measure that will eventually bring freedom back to the island. But the timeline for new elections in Cuba will be even longer than the one he wants in Venezuela.
How does the situation with Iran impact this forecast? I generally view them as two separate issues. Convincing Cuba to work with the US is far easier than the military operation involving Iran. The higher oil prices caused by the shutdown of the Strait of Hormuz make the Cuban regime more desperate. Importantly, Trump is not planning on militarily taking over or bombing Cuba. My forecast about the future would change if this required military force, but it doesn’t.
Process note: I began this newsletter draft as a scenario memo, mapping out different potential outcomes. I included it yesterday in my subscriber-only newsletter about other Cuba issues. However, the more I thought about it, the more I became convinced that some sort of negotiated accommodation was by far the most likely scenario to occur this year. For the record, here is my scenario matrix that I began with:
My current take on Venezuela’s political stability is much more volatile. I owe an update to my Venezuela scenarios, but the brief version is that while consolidated dictatorship under Delcy is one possibility, various other changes up top, democratization, or just utter chaos also remain plausible. The scenarios are more complex than those in Cuba. It’s absolutely possible that Delcy Rodriguez loses power in Venezuela and we’re still talking about Delcy-like leaders in other parts of the world. She’s a meme at this point.