Trump Administration Does Not Expect a Cuban Uprising, But Keeps the Door Open

The Trump administration is prosecuting a multi-instrument pressure campaign against the Cuban government, combining tightened sanctions, an energy blockade, tariff threats against third-country oil suppliers, and publicly signaled military options, with the stated objective of forcing political and economic liberalization in Havana. What U.S. officials are not building into their leverage calculus, according to POLITICO, is a spontaneous popular uprising against President Miguel Díaz-Canel's government.

The legal architecture undergirding the campaign is substantial. On Jan. 29, 2026, President Trump signed Executive Order 14380, declaring Cuba "an unusual and extraordinary threat" to U.S. national security and invoking the International Emergency Economic Powers Act (IEEPA) to authorize tariffs on imports from any country that directly or indirectly supplies oil to Cuba ^[1][2]. That order followed a June 2025 National Security Presidential Memorandum that established the policy framework for the broader pressure campaign ^[3]. A subsequent executive order issued in May 2026 broadened IEEPA-based sanctions to cover individuals and entities that support Cuba's security apparatus, are complicit in corruption or human rights violations, or act as agents of the government, with secondary liability for foreign financial institutions that process transactions with designated parties ^[3][4]. The State Department also designated Raúl Castro and five others before a U.S. grand jury in the Southern District of Florida returned an indictment against Castro for allegedly ordering the 1996 shootdown of two Brothers to the Rescue aircraft ^[22][16].

The energy pressure has produced measurable results on the ground. After Venezuelan oil shipments to Cuba effectively ceased following the U.S. military operation that removed Nicolás Maduro from power in January 2026, Cuba's government declared emergency fuel measures; Cuba's president acknowledged the country had received no oil shipments for three months as of early March ^[1]. Mexico subsequently halted its own shipments, widely interpreted as a response to U.S. tariff pressure, and at least one Russian tanker bound for Havana diverted from its course before reaching Cuban waters ^[5]. Cuba now faces daily power outages of up to 20 or more hours in some areas, acute food shortages, and strained medical supply lines ^[8][16].

Against that backdrop, U.S. officials who spoke to POLITICO assessed a popular uprising as unlikely in the near term. The analytical anchor for that judgment is the July 11, 2021, protests, the largest mass demonstrations in Cuba since the 1959 revolution ^[9]. The Cuban government responded with systematic force. Rights groups, the European Union, and the United States collectively estimate that between 1,000 and 1,500 people were jailed in connection with those protests, with several hundred still serving sentences, many for broadly drawn charges including "sedition" and "public disorder" ^[12][8]. Human Rights Watch documented due process violations, beatings, and prolonged solitary confinement ^[8]. The deterrent effect has been durable: Reuters reporting from the neighborhoods where 2021 clashes were most intense found that residents remember the crackdown clearly, and that most assessed another large-scale uprising as unlikely ^[12]. Dissident leaders have been largely imprisoned or forced into exile, and the government has demonstrated the capacity and willingness to cut internet access at the first sign of unrest ^[12].

Demographic attrition compounds the structural problem. Cubans in their 20s and 30s, the cohort that typically sustains protest movements, have emigrated at high rates; the Cuban government's own migration crisis drove more than 850,000 arrivals to the United States between 2022 and late 2024 alone ^[3]. Ricardo Zuniga, a former senior U.S. diplomat who worked Cuba policy, told POLITICO that the administration's aggressive rhetorical posture has itself dampened the likelihood of street action. His observation, attributed to POLITICO, was that Cubans waiting for U.S. military intervention may be less inclined to take personal risk in the interim [POLITICO].

Secretary of State Marco Rubio marked Cuba's Independence Day on May 20 with a Spanish-language video message addressed directly to the Cuban population, the first such direct appeal he has made in his current role ^[16]. Rubio, whose parents immigrated to the United States from Cuba, blamed the regime for the island's material deprivation. "The real reason you don't have electricity, fuel, or food is because those who control your country have plundered billions of dollars," he said, targeting GAESA, the military-controlled conglomerate that Rubio alleges holds $18 billion in assets and controls roughly 70 percent of the Cuban economy ^[16][22][23]. Rubio simultaneously announced a conditional U.S. offer of $100 million in food and medicine, contingent on distribution through the Catholic Church or other nongovernmental organizations to prevent diversion through GAESA ^[16][22].

With the fourth anniversary of the July 2021 protests approaching on July 11, the administration may use the date as a trigger for additional sanctions or designations. The State Department used the third anniversary in 2025 to impose visa restrictions on Cuban judicial and prison officials under Section 7031(c) and update the Cuba Restricted List ^[10]. The regime, tracking the same calendar, can be expected to pre-position its security apparatus. Whether Washington moves to intensify pressure or whether conditions inside Cuba generate any organized response, the administration has signaled it will treat a popular uprising as a bonus rather than a strategy.