UPDATE 6.9.26: In the Trump administration’s pressure campaign against Cuba’s communist regime, it has changed tactics compared to previous administrations on one very important point; the treatment of refugees leaving Cuba.
In the past, reports Gil Guerra in Foreign Policy, American administrations created a welcoming environment for Cuban refugees. Allowing safe passage to the U.S. for some of the Cuban regime’s greatest critics and their families reduced pressure on the communists, and was even encouraged by them in order to rid the country of potential dissidents. But now they are being forced to look for shelter in other places, as the Trump administration clamps down on refugees coming to the U.S. This could put greater pressure on the Cuban regime, and lead to unrest in the country. Guerra writes:
Shortly after taking office for his second term, Trump issued an executive order stating that “the policies, practices, and actions” of the Cuban government “constitute an unusual and extraordinary threat … to the national security and foreign policy of the United States,” owing to Havana’s ties with U.S. adversaries, including China and Russia. As a result of Trump’s hard-line Cuba policy, including a monthslong U.S. oil embargo, the island’s economic situation has further deteriorated. Inflation is soaring, basic goods are scarce, fuel is gone, and Cuba’s aging power grid is nearing collapse.
Read more here.
UPDATE 5.15.26:
The New York Times reports that CIA Director John Ratcliffe made a rare visit to Cuba to meet officials amid economic crisis and strained U.S.-Cuba relations.
He delivered a message from President Donald Trump saying improved relations depend on major Cuban reforms, while Cuban officials called for continued dialogue.
The visit is notable given long-standing Cold War-era tensions between the two countries.
UPDATE 5.14.26:
Barron’s reports that Cuba has ‘run out’ of fuel. Cuba is facing severe nationwide blackouts after the government said it has exhausted oil reserves needed for power generation, worsening an already fragile electricity system.
The crisis has sparked rare protests in Havana, with authorities blaming US sanctions and fuel import restrictions for the ongoing energy shortages.
UPDATE 4.24.26: Rep. Carlos Gimenez (R-FL): Cuba poses a security threat to the United States. President Trump has said, ‘enough is enough.’
Rep. Carlos Gimenez (R-FL): Cuba poses a security threat to the United States. President Trump has said, ‘enough is enough.’ pic.twitter.com/sjgZtXigCU
— Molly Ploofkins (@Mollyploofkins) April 23, 2026
UPDATE 3.31.26: Sovereign capitalism for Cuba? Fidel Castro’s grandson suggests that he would welcome a deal with the Trump administration.
NEW: While drinking a beer, Fidel Castro’s grandson says he is a capitalist and says if it were up to him, he would welcome a deal with President Trump during an interview with CNN.
“There are many people here [in Cuba] who want to have capitalism with sovereignty.” pic.twitter.com/zrIvQ6uH4Z
— Collin Rugg (@CollinRugg) March 30, 2026
UPDATE 3.27.26: Miguel Díaz-Canel said Raúl Castro is helping guide early-stage talks between Cuba and the United States, even as tensions rise amid sanctions, energy shortages, and a deepening humanitarian crisis on the island, according to Andrea Rodriguez of the AP. Rodriguez writes:
Former Cuban President Raúl Castro is involved in talks between the island and the United States, Cuban President Miguel Díaz-Canel said Wednesday. […]
Prolonged power outages and a near-paralysis of economic and social life are the visible consequences on the island, which in the last week experienced two nationwide blackouts that left millions without electricity as Cuba’s power grid continues to crumble. […]
Raúl Castro, who succeeded his brother, Fidel, as president, led historic talks with former U.S. President Barack Obama in 2014 that led to the reopening of embassies and re-establishment of diplomatic relations.
Trump has opposed such policy, tightening sanctions even further, exacerbating a deep economic crisis to the extreme of the current energy blockade. […]
UPDATE 2.24.26: Marcos Falcone calls the crisis currently unfolding in Cuba, “its worst yet,” and blames the Cuban government. He writes:
Daily life for Cubans is just as nightmarish. Recent videos filmed by locals depict an almost empty Havana, as the country’s capital can no longer afford to keep public transportation running. The federal government has mandated remote work, and universities are also operating virtually, though a lack of energy effectively means they have shut down. Food shortages, which have long been a part of Cuba’s reality, have become more acute.
The decline of Cuba’s economy is producing mass emigration, even more than in the past. A recent study suggests that up to 1.7 million Cubans fled the country between 2020 and 2024. That study placed the 2024 population of Cuba at 8 million people. For comparison, the 2021 US Census estimated the number of foreign-born Cubans living in the US to be 1.3 million.
Even though recent US action may be putting more pressure on Cuba, the dismal performance of the Cuban economy is a function of the Cuban Communist Party’s central planning, which has been uncontested since the establishment of the dictatorship in 1959. Supporters of the Cuban regime point to the 1960 US embargo as the source of Cuba’s economic problems. However, research suggests that between 1959 and 1989, the embargo was only responsible for “a trivial part (less than a tenth)” of the income loss that can be attributed to the Cuban Revolution. There is no reason to believe that the sanctions, and not communism itself, have played a larger role in the years since.
UPDATE 1.13.26: President Trump has put Cuba on notice that there will be no more money or oil coming to it from Venezuela.
“…THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA – ZERO! I strongly suggest they make a deal, BEFORE IT IS TOO LATE. Thank you for your attention to this matter.”- President Donald J. Trump pic.twitter.com/bHEIysJ7q1
— The White House (@WhiteHouse) January 11, 2026
To Avoid Capture, Go Somewhere Unknown
“If you are really trying to avoid capture, you go to places people don’t know about,” a former US military officer told the WSJ.
Escape: 101
“You wonder why Maduro didn’t go to some nondescript apartment in the middle of Caracas or the countryside.”
Intelligence is critical in protecting VIPs. Patterns of life, daily habits, and routine can seem mundane, but become critically important in helping to keep VIPs safe. For example, it is well known that Russian President Vladimir Putin goes to great lengths to maintain secrecy about his movements, residence details, or workspaces.
Become Unknown
Is there trouble for Havana’s leaders? Maduro’s capture was bad enough. There was more carnage. Cuba reported that 32 officers assigned to a safety detail for Venezuela’s strongman were killed. This doesn’t augur well for Cuba’s leaders.
Cuban intelligence, known for decades as Cold War stars, just had its invulnerability punctured.
U.S. elite forces descended on Maduro’s compound at around 2 a.m. local time Saturday, grabbing him and his wife before they could escape to a safe room, said Gen. Dan Caine, the chairman of the Joint Chiefs of Staff.
Cuba’s defeat indicates its weakness, according to María Werlau, author of “Cuba’s Intervention in Venezuela,” a book published in 2019.
Relied upon by the Soviet KGB for its extensive informant networks in Latin America and Africa, Cuban expertise to protect allies, detect unrest and suppress dissent became a lucrative export. After the collapse of the Soviet Union, Cuba’s security and intelligence services secured a lifeline from oil-rich Venezuela as Havana inched closer to economic collapse.
Old School Craft
Despite a U.S. armada threatening the Venezuelan leader for months from the Caribbean, how did Cuba’s security detail fail to defend Maduro? Perhaps even worse, Cuba’s security failed to inflict any damage on the Americans, points out Jorge Castañeda, Mexico’s former foreign minister and author of several books about Cuba’s regime. “This means the Cubans weren’t where they needed to be, with the strength they needed to have.”
These intelligence flaws are likely to hurt the communist regime at home, writes the WSJ, especially should Cuba lose its economic support and subsidized oil shipments amid an unprecedented economic implosion.
“The people can go hungry, but the repressive apparatus must have privileges,” offers Enrique Garcia, a former Cuban intelligence officer who defected to the U.S. “If the regime loses all economic capacity, no system can withstand it.”
