Could it actually work?

For almost seven decades, Cuba has been the unfinished business of American foreign policy.

Every president talks about Cuba. Some tighten sanctions. Some loosen them. Some try engagement. Some try pressure. 

The regime survives all of it. 

The Castros outlasted Eisenhower, Kennedy, Johnson, Nixon, Carter, Reagan, both Bushes, Clinton, Obama, Biden, and Trump’s first term. They survived the fall of the Soviet Union. They survived the loss of Venezuelan oil. They survived poverty, blackouts, exile waves, dissident movements, and generation after generation of Cuban Americans waiting for justice.

But when Donald Trump says Cuba is on his mind, people should probably listen.

The indictment of Raúl Castro this week is not just another sanctions announcement. It is not a strongly worded statement from the State Department. It is a murder indictment against the man who, for decades, represented the hard military spine of the Cuban Revolution.

The case centers on the 1996 shootdown of two Brothers to the Rescue planes, which killed four people: three American citizens and one legal permanent resident. The United States has long maintained that the planes were in international airspace. Cuba has long claimed self-defense. But now prosecutors are saying something more direct: that Raúl Castro, then head of Cuba’s armed forces, authorized deadly action and that the order traveled through the Cuban military chain of command.

This is no longer merely about “Cuba” as an abstract adversary. It is about named men, named victims, and an old crime that the United States says it has not forgotten.

Trump clearly understands the symbolic power of this. 

His comments on the subject were aimed straight at Cuban Americans, especially in Miami. He said this was a “very big moment” for people whose families were ruined by the regime and who still want to see their families and homeland free. That is not incidental. The indictment was announced in Miami for a reason. It speaks to memory, exile, grief, and unfinished justice.

But it also speaks to strategy.

Trump understands his audience. And he is applying pressure the way he applied it in Venezuela. 

The Maduro example hangs over all of this. Maduro was indicted, isolated, and eventually captured and brought to the United States. His successor, Delcy Rodríguez, became a working partner for Washington. That is the model. Criminal exposure at the top. Economic pressure from the outside. A search for someone inside the regime willing to cut a deal before the whole structure collapses.

The question is whether Cuba has a Delcy.

Venezuela had factions, wealth, oil, private power centers, opposition politics, and a regime that behaved in many ways like a corrupt syndicate. Cuba is different. Cuba is older, poorer, more sealed, and more disciplined. It is a true security state. The Communist Party, Interior Ministry, and military are not just institutions. They are the skeleton of the regime. They monitor society down to neighborhoods, workplaces, schools, churches, and concert halls.

There may be no obvious Cuban insider who can be peeled away, blessed by Washington, and installed as a transition figure.

But that does not mean Trump’s strategy is foolish. It means it is a gamble.

Cuba is not stable in the meaningful sense. It is controlled. Those are not the same thing. The island is suffering blackouts, fuel shortages, food scarcity, mass emigration, and deep economic decay. 

The old arrangement — repression at home, subsidy from abroad — is failing. Venezuela can no longer rescue Havana. Russia and China may offer rhetorical support, but the U.S. would never allow either nation to gain to firm a physical foothold its backyard. The regime can still arrest dissidents. It can still intimidate families. It can still force people into exile. But it cannot keep the lights on.

That is the opening Trump sees.

His public line is interesting. He called the indictment historic, but when asked about escalation, he said no. He said he does not think escalation is necessary because Cuba is already falling apart. That is classic Trump leverage politics. He is not saying, “We are coming in tomorrow.” He is saying, “Look around. You are out of oil. Your country is breaking. Your old protectors are gone. Your leaders are exposed. We can help, but not forever.”

That is pressure with an exit ramp — an excellent negotiating technique.

The humanitarian-aid offer is part of the same message. So are the talks in Havana. So are the warnings. This is not random chaos. It is a squeeze paired with an offer. The United States is saying: reform, negotiate, open the system, or face consequences.

Could it backfire? Of course. The indictment could harden the regime. If the men around Raúl Castro believe there is no future for them except prison or humiliation, they may choose to hunker down. Dictatorships often become most dangerous when they feel cornered.

But the opposite is possible too. The indictment may tell younger Cuban officials that tying their futures to a 94-year-old revolutionary icon is no longer rational. It may tell the military that the regime’s survival strategy has become a dead end. It may tell everyone in Havana that Maduro was not an exception.

For decades, American policy toward Cuba has swung between wishful engagement and symbolic punishment. Trump is trying something more direct. He is treating the regime as vulnerable, not permanent. He is tying old crimes to current leverage. He is speaking to Cuban Americans not as a voting bloc to be flattered, but as people who have waited a very long time to hear an American president say: we remember.

Will it work?

No one knows. Cuba is not Venezuela. There may be no easy internal replacement, no clean transition, no friendly figure waiting to make a deal.

But for the first time in a long time, Washington seems to understand something important: the Cuban regime is not strong because it is loved. It is strong because people believe it cannot be moved.

Trump is testing that assumption.

And maybe it is about time.

(Contributing writer, Brooke Bell)