CIA in Cuba: The Communists Allow the Old Enemy In

After months of sustained economic, diplomatic and military pressure on Cuba’s communist leadership, the United States is turning the screws even further on Havana, and they’re using the Central Intelligence Agency, with its long history on the island, to do it.

Cuban state-controlled media reported on Thursday that the U.S. government had requested that a delegation headed by CIA chief John Ratcliffe be sent to Havana, a request the Cuban government granted. The CIA later posted images of Ratcliffe meeting top Cuban officials in the island’s capital.

Ratcliffe is believed to have met with the head of Cuba’s intelligence services, the country’s interior minister, and Raúl Guillermo Rodríguez Castro-the grandson of former Cuban President Raúl Castro and great-nephew of revolutionary leader Fidel Castro. The conversations were intended to ease tensions between the two countries, according to the Cuban state media readout, after weeks of fruitless talks.

But separately, the U.S. is making preparations to indict Raúl Castro, U.S. media reported on Thursday.

The possible indictment will likely home in on the Cuban military shootdown of two civilian planes operated by an anti-Castro exile group in early 1996, killing four people and triggering a new diplomatic crisis between Havana and Washington.

Combined, this is “unprecedented” pressure on Havana, said Connor Pfeiffer, who advises Congress on foreign policy and intelligence in the Western Hemisphere with the Foundation for Defense of Democracies Action, an activist and lobbying group.

Along with two rounds of new sanctions in the past few weeks, the U.S. is tightening its grip on Havana beyond the painful strangulation of fuel to the island, Pfeiffer told Newsweek.

Accepting a CIA meeting, not least because of the agency’s history with Cuba over the failed Bay of Pigs attempt to overthrow Castro’s government in 1961, is a “huge sign of weakness” for Havana, Pfeiffer added.

The CIA is increasingly becoming the “visible tip of the spear in American foreign policy,” said Brian Fonseca, the director of the Jack D. Gordon Institute for Public Policy at Florida International University.

The agency is becoming more prominent in the Western Hemisphere, he told Newsweek, and is one of the ways the U.S. is now showing its “ready to go to the next level” in its showdown with Havana.

Blockades and Sanctions

President Donald Trump ramped up decades of U.S. pressure on Cuba in January, squeezing the island with a new fuel blockade, alluding to military action against Havana once U.S. operations in Iran wrap up and slapping the country with fresh American sanctions, including on its defense and financial sectors.

Cuba was heavily dependent on Venezuela’s oil exports before U.S. forces swept into Caracas and captured then-leader Nicolás Maduro, bringing him to New York to face narcoterrorism charges.

The U.S. then said that any country supplying Cuba with fuel could face punitive tariffs, and has allowed only a small shipment from Russia to reach port in Cuba for “humanitarian” reasons.

Despite this limited lifeline, Cuban energy minister Vicente de la O Levy said on Wednesday that the island’s energy system was in a “critical state” and that all supplies of diesel and other fuels were drained. Only small amounts of gas remained, he said.

Blackouts have become routine, sometimes for up to 22 hours a day, according to Cuban authorities. Protests have broken out in waves as garbage piles up in the streets, the vital tourist trade drying up, and residents sinking into what the United Nations has called “energy starvation.”

Cuba has admitted the situation is “tense,” but has hit back at U.S. claims that Havana has refused to accept $100 million in humanitarian aid-which would be handled by the Catholic Church, not the government-in exchange for “meaningful reforms” within its leadership.

With the State Department, Justice Department, White House and CIA working together, this could be what topples the longstanding regime, although its staying power isn’t to be underestimated, Pfeiffer said.

Cut off from its fuel imports, its allies and its hard-cash sources like nickel exports and staring down public ire, Havana is in “its most dire economic situation since the end of the Soviet Union,” Pfeiffer said.

Moving to indict Raúl Castro, who is now closing in on his 95th birthday, could be a way for the U.S. to justify its intensifying pressure campaign and offer a sense of perceived justice for Cuban-Americans and human rights activists who have long pushed for Havana to face consequences over the shooting down of the two planes operated by exiled Cubans 30 years ago.

The Cuban government said at the time the aircraft were inside Cuban airspace, while the U.S. insisted the planes were in international airspace. A later probe by United Nations aviation authorities concluded the aircraft were outside Havana’s jurisdiction but acknowledged the Brothers to the Rescue group operating the planes had previously violated Cuban airspace.

Venezuela Parallels

Wrapping up Castro in an indictment could also be setting the stage for a Venezuela-type operation, some experts predict.

The CIA was authorized to carry out covert operations in Venezuela before U.S. forces entered Caracas, and Ratcliffe was one of the first visitors to the city after Maduro’s removal.

“A lot of the same aspects of the playbook are being employed here,” said Pfeiffer.

Maduro, along with a number of his top officials, was indicted on multiple charges in U.S. federal court and faced down a massive U.S. military buildup near its shores ahead of the U.S. operations at the start of the year.

The U.S. is also thought to have ramped up intelligence-gathering flights off the Cuban coast, while the White House has repeatedly hinted at a possible military takeover of the island.

Cuba, 90 miles from Florida, is close enough to the mainland U.S. and major military bases that a carrier strike group wouldn’t be needed in U.S. operations against the island. Any military action could be run from the U.S. without having to deploy ships near Cuba’s shores, unlike in Venezuela and Iran.

But experts say a Venezuela-style leader grab is unlikely. Cuba’s leadership is more spread out, and the capture of President Miguel Díaz-Canel or Castro would not have the same effect as Maduro’s highly publicized trip to an American jail.

Díaz-Canel told Newsweek in an interview in the Cuban capital last month that the country was prepared to fight any U.S. military attack, although U.S. officials have said there are no imminent plans for invading Cuba.

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This story was originally published May 15, 2026 at 9:44 AM.