Following weeks of warnings from the Trump administration and a Jan. 29 executive order declaring that Cuba poses an “extraordinary threat” to the United States and threatening to impose tariffs on any country that ships oil to Cuba, the administration’s top diplomat in Havana, Mike Hammer, told Telemundo last week that change would come to Cuba in 2026. He cited the precedent of U.S. intervention in Venezuela and referenced conversations with unspecified Cuban officials.
For more than 20 years, Havana’s alliance with Caracas provided Cuba with crucial subsidized oil. Now, the Trump administration is cutting off that flow of oil while also choking off revenue from tourism. The administration hopes that this will pressure President Miguel Díaz-Canel or other regime leaders to act — the executive order provides an off-ramp for Cuba if it takes steps to align with the United States on security issues, and President Donald Trump has expressed a willingness to “work a deal.”
For a Cuban regime that is presiding over a country in free fall, Trump’s clear desire to negotiate could represent its best and last opportunity to avoid the country’s collapse. Díaz-Canel should consider how other leaders who have sought to overcome hostility by reaching out to Trump, most recently Colombian President Gustavo Petro, have been rewarded for their efforts.
The Cubans should also be encouraged by the administration’s practical approach to Venezuelan interim President Delcy Rodríguez. Although it is early in that process, so far, Trump has not focused on dismantling the regime or scheduling elections, to the chagrin of democracy proponents.
Yet these compelling reasons may not matter if no one within the regime has both the authority and incentive to act on them. Cuba is no longer a one-man dictatorship but a coalition regime. Díaz-Canel is the president, but has no independent power and owes his position to the Castros. A deal with the U.S. would likely require buy-in from too many actors, including 94-year-old Raúl Castro and other regime stalwarts, his son and intelligence chief Alejandro Castro Espín, and hard-liners controlling the military and state enterprise GAESA, which operates as a state within a state and controls 40% of the economy.
If the regime leadership refuses Trump’s offer, the administration will be tempted to escalate economic pressure using the extensive leverage it has over Cuba. However, given existing shortages of food and medicine, Washington should think twice about whether its approach would contribute to a humanitarian disaster. The regime has withstood past periods of deprivation and probably feels it can ride out U.S. pressure, regardless of the suffering of ordinary Cubans.
Until now, Cuba’s precarious state has been a result of the regime’s own commitment to a command economy and its tolerance of military elites siphoning cash from tourism and other profitable sectors. The Trump administration should keep the focus on the regime’s record of mismanagement and not become a protagonist in Cuba’s suffering, which would galvanize public opinion in the U.S. and around the region, undercutting other objectives.
Trump should also consider what end state he wants in Cuba. If he does succeed in nudging Cuba toward change, restarting the Cuban economy will be challenging enough without also having to recover from catastrophic conditions. Cuba does not have Venezuela’s oil reserves or any other resources that can quickly stabilize its economy.
Trump’s instinct to pursue a deal is correct, but given the diffuse decision-making within the regime and the risk-averse climate this creates, the administration should avoid the kind of maximalist approach that would exacerbate a bunker mentality within the regime. Washington should instead offer a clear, achievable pathway: measurable steps on foreign policy alignment in exchange for calibrated sanctions relief.
An initial framework might include concrete commitments from Cuba to curb intelligence sharing with China and Russia and restrictions on Chinese military facilities, areas where Cuban behavior genuinely threatens U.S. interests. In return, the administration could offer phased relief: allowing resumption of oil shipments and eventually relaxing travel and trade restrictions. Discussion of elections and matters that are existential to the regime might be left to a later phase of discussions.
Trump’s transactional pragmatism in negotiations could open the door for a Nixon-to-China moment with Cuba — delivering historic progress where decades of pressure failed. But this requires commensurate pragmatism in tactics, recognizing that further immiserating Cubans is more likely to entrench the regime than dislodge it.