MIAMI-DADE COUNTY, Fla. — As the Trump administration ramps up pressure on Cuba by siphoning off critical Venezuelan oil imports, the president is urging the communist-run island to cut a deal with the United States.

Experts are weighing in on the future of the regime.

“The main goal here is to convince the Cubans — looking at Venezuela — it could happen to them, and perhaps there is a waiting game involved because the Cuban government is in dire straits,” said Sebastián Arcos of Florida International University’s Cuban Research Institute.

Asked what it means for Cuba to “make a deal,” Aaron Rosen, the founder and president of the World Affairs Council of Miami, pointed to Venezuela as a case study.

“The Venezuela case shows us that Trump is not as concerned with quote-unquote ‘regime change’ and ‘democracy’ flourishing as maybe some of his predecessors, particularly the neoconservative movement under President (George W.) Bush,” Rosen said. “He is looking for a quick win that he can market as a victory, with some type of concessions that he can say shows U.S. dominance and really hegemony in the Western Hemisphere.”

Rosen said that, in Cuba’s case, that could mean pledging to release political prisoners, some kind of “re-orientation” toward the United States, or commercial contracts for U.S. companies to come and develop Cuba — even the idea of a “new Riviera,” as Trump has talked about.

But he added that such offers have typically not been well-received by the Cuban government, because they would require ceding control over the economy, something it has been hesitant to do.

“The Cuban government has a history of surviving difficult circumstances, and this could be another case,” Arcos said. “Although this could be it — this could be the last crisis. We could see regime change sooner rather than later.”

Arcos said that while he is hopeful a worsening economic climate could eventually trigger a pivot toward democracy, any change in that direction would likely take years — and only if the U.S. government can identify new transition leadership that maintains stability on the island.

“It is not going to happen immediately,” Arcos said. “It might take a while. It is not going to happen tomorrow. It is not going to happen next week. This is going to take a while.”

Analysts also point to a historical parallel: Cuba in the 1990s, after the collapse of the Soviet Union ended the flow of cheap, subsidized oil that had propped up the socialist state.

“When the Soviet Union collapsed in the ’90s, Cuba went through their special economic period, also called the ‘Special Period,’” Rosen said. “It is because their chief subsidizer and ally collapsed, and the Cuban economy similarly also collapsed. During that period, the Cuban government experimented with austerity measures. They started opening up to more tourism and looked for different ways to run the economy.”

Rosen said to expect Cuba to be defiant again: it may double down on austerity.

“There were a lot of parallels to today — rolling blackouts, mass poverty, shortages of medical and food supplies,” Rosen said. “But ultimately, what they did not do is give up political control. They just sustained, they maintained power, and eventually Hugo Chávez in Venezuela came along and was able to provide subsidized oil to Cuba to help prop them up.”

Rosen said the difference now is that Cuba is again in a position where its chief subsidizer, Venezuela, has collapsed in its ability to serve that role — but this time, “there is not really someone else on the horizon that is going to save” the regime.

“The Chinese and the Russians ― they have a commercial, and to a degree political, partnership with Cuba, but not to the extent that Venezuela was supporting Cuba,” Rosen said. “Recently, the Mexicans are also in the spotlight for supporting Cuba. The difference is that Mexico, for the past two or three years ― they have been sending oil to Cuba, but it hasn’t been a dramatic amount.”

He added that the Cuban government has faced similar situations before and has never shown a willingness to give up control.

“That is not what they are used to, and usually dictatorships don’t have a good track record of giving up control, handing over power, and democracy flourishing,” Rosen said. “Usually they hold off until the end.”

Arcos agrees that Mexico’s support is not enough to keep Cuba financially afloat.

“Venezuela represents 30 percent of the oil Cuba consumes in one day — 110 million barrels,” Arcos said. “Without that, Cuba is limited to a few barrels from Mexico, fewer yet from Russia and local production, which is about 40% of what they need and is very, very bad quality oil. So I don’t think they can survive as a normal functioning economy. The country cannot sustain this.”

Arcos said Mexico may soon be forced to choose between maintaining a close relationship with Cuba or one with the United States.

“And I think you can guess which one they will choose,” he said — especially with a trade deal up for review this summer.

Copyright 2026 by WPLG Local10.com - All rights reserved.