Regime change in Cuba could benefit wealthy Republicans

Even for Donald Trump, who is in the middle of a conquistador phase, the declaration was unusually crude. “I do believe I’ll be having the honor of taking Cuba,” he said in the Oval Office on March 16. “Whether I free it, take it — I think I could do anything I want with it, you want to know the truth. They’re a very weakened nation right now.” 

The president is correct: Cuba is in a fragile state at the moment. But that’s mostly due to Trump, who instituted an oil blockade against the island nation in the wake of January’s Venezuela operation. Cuba is now on the verge of collapse — and the Cuban people are suffering greatly because of it. 

The country has suffered three major blackouts this month, leaving 10 million people without power for days at a time. Hospitals are unable to perform surgeries, food is spoiling, garbage is everywhere because there is no fuel for the government trucks to pick it up. School has been canceled. Businesses are shuttered; there is little to buy or sell.

The New York Times reported the administration is seeking to oust President Miguel Díaz-Canel from power while allowing the island’s Communist government to remain in place — a repeat of what they allowed in Venezuela — and giving Trump a “symbolic win.” As his botched Iran “excursion” has begun to falter, taking Cuba would be a soothing salve for the president’s ego.

Significantly, it could also be a boon for rich Republicans. While the Times reported that the administration could keep “the repressive Communist government that has ruled Cuba for more than 65 years” in place with a new leader — in effect, following the model Trump set in Venezuela — the Atlantic noted that plans could also give “wealthy Republican donors with Cuban ancestry” leadership roles in a transition or even permanent government. Current discussions between the U.S. and Cuban governments are said to include “restitution for owners of property seized by the Cuban government” during the 1959 revolution that brought Fidel Castro to power — many of those wealthy expatriates settled in south Florida and became Republicans — and “securing broad U.S. latitude to invest, develop, and ultimately capitalize on Cuba’s under developed cities and beaches.”

Political change, in other words, is not necessarily the priority. As was the case with Venezuela, Trump could not care less about freedom and democracy, even though they have used it as an excuse to declare a national emergency in order to legally justify any actions they will end up taking with Cuba. This is all about business, and it’s unlikely they will listen to anyone who doesn’t have a financial stake in the country’s future and there are plenty of people anxious to get started. Idealists need not apply, especially since Secretary of State Marco Rubio is calling most of the shots. 

After a lifetime agitating for the overthrow of the communist regime in his father’s native country, Rubio will now by all accounts be happy to work with the repressive regime as long as they are willing to welcome the capitalists. He spoke at length about this at the recent Munich Security Conference, acknowledging that while Cuba faces other issues, “the fundamental problem [is that] Cuba has no economy.” 

The Trump administration has made sure of that, capitalizing on the tremendous economic and political stress the country has been under since the fall of the Soviet Union, as well as the recent sanctions and tariffs leveled by Trump following his return to office in January 2025.

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But relations between Cuba and the United States have been fraught for centuries. The U.S tried to buy the country from Spain throughout the 19th century and ended up occupying it many times over the years. In a strange circumstance, Cuba even achieved its independence as a result of the American victory in the Spanish-American War. First as an American protectorate and then as an independent nation, Cuba was exploited by Washington to such an extent that it was pretty much owned by U.S. interests before the 1959 revolution.

The anti-communist politics of the Cold War and the tensions caused by the Cuban Missile Crisis dictated the antagonistic relationship between the two countries for decades until Barack Obama began the process of normalizing relations in December 2014. Both commerce and political reform were on the agenda, and Cuba began to emerge from its isolated existence. But that progress was reversed when Donald Trump took office in 2017 and, as he did with most foreign policy, trashed all agreements that had been signed under Obama. The two countries were again on the road to normalization by the end of Joe Biden’s presidency, but Trump’s win has taken relations to a place we haven’t seen since the late 19th century, with the U.S. openly seeking to dominate the island — if not own it altogether. 

According to the Atlantic, one of the people familiar with the administration’s plans said, “We control our hemisphere, and we have the ability to do this. We want these hostile regimes out of our hemisphere, and we’re going to set up the business community, because we don’t believe in diplomacy.” 

They believe someone’s going to make money and, if you had to guess, one of them will almost certainly be Trump himself. 

The president apparently talked about financial opportunities in Cuba with government officials and the Trump Organization during his first term, and he was excited about the possibility of Trump-branded hotels and condominiums on the island. A source said that “he’s interested in Cuba as a market for him, and completely agnostic about the politics.” Trump doesn’t care, they claimed.

All this brings to mind a famous scene in “The Godfather Part II.” As the mobster Hyman Roth and Michael Corleone plot to take over even more of a Cuba on the verge of revolution, Roth says:

Here we are, protected, free to make our profits without Kefauver, the god d**n Justice Department and the FBI 90 miles away, in partnership with a friendly government. Ninety miles! It’s nothing! Just one small step, looking for a man who wants to be president of the United States, and having the cash to make it possible. Michael, we’re bigger than U.S. Steel.

The mobsters were thwarted back then. But now it appears that Donald Trump and Marco Rubio are preparing to make their long-deferred dream come true.

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