Letter from Washington: Trump’s Endgame on Cuba is Unclear; the Political Risks are Not
By Filipa Jorge
February 13, 2026
The Trump administration’s National Security Strategy and so-called “Donroe Doctrine” have shifted U.S. foreign policy focus to the Western Hemisphere.
This has resulted in controversial moves such as the targeting of drug-smuggling boats in the Caribbean and Eastern Pacific, as well as the military operation in Venezuela that removed Nicolás Maduro. The latter widened the target on Cuba, resulting in a ramp-up of President Trump’s “maximum pressure” campaign on the island.
But with Cuba facing imminent humanitarian and economic crises, the question of what the U.S. endgame is for the island 90 miles off the coast of Florida — whose fraught strategic history with Washington eclipses its size and population — looms large.
Cuban airports this week ran out of jet fuel, leading Canadian and other international airlines to cancel flights to the island. Moscow is going to start evacuating Russian tourists. The hit to Cuba’s tourism industry (Canadians comprise the top market at 750,000- 1 million per year) cuts off an important revenue stream for the government and access to foreign currency at a time when the economy is on the brink of collapse.
While Cubans have struggled with tightened US sanctions, rolling electricity blackouts, shortages of essential goods and services, and dwindling hard currency reserves, the Trump administration’s latest actions to impose an oil embargo have, by all indications, led to the island’s worst economic crisis since the 1959 revolution.
Emboldened by the success of its military operation in Venezuela, the Trump administration has turned its focus to eradicating the alleged national security threat posed by Cuba.
Not only did the Trump administration cut off delivery of heavily subsidized Venezuelan oil, but it threatened tariffs on countries selling or supplying oil to Cuba (note Trump’s Executive Order). Not wanting to provoke the US and risk damage to economic ties (especially amid an already problematic USMCA renewal process), Mexico — Cuba’s largest supplier after Venezuela — ceased oil deliveries. Havana responded by rationing fuel and imposing emergency measures, but Cuba is expected to run out of fuel before the end of February.
Concerned by the risk of humanitarian crisis, the U.S. State Department and Mexico have increased aid to Cuba. Russia is also considering what assistance to provide.
Under pressure, President Miguel Diaz-Canel has offered to negotiate. Talks between American and Cuban officials are ongoing, but reaching an agreement may prove more difficult than it was in Venezuela.
The White House has not disclosed specific aims in negotiations though the regime change component seems to be a priority. This, and other factors listed below, make it highly unlikely that the U.S. can — or even wants to — replicate the model of replacing the figurehead but keeping the regime in place while increasing U.S. access to key economic sectors.
- The White House is constrained by U.S. law (Cuban Democracy Act and Cuban Liberty Act) and, perhaps more importantly ahead of the midterms, the long-intrinsic domestic factor of politically active Cuban-American voters, who demand a democratically elected government, reparations/return of property, and a transition to a market economy.
- GOP members (especially from Florida) largely support the embargo, and while the MAGA base is increasingly supportive of a muscular U.S. foreign policy, less than 30% back military action in Cuba. Cuban American Secretary of State Marco Rubio, widely seen as a Cuba hawk in part based on his personal history, has supported regime change in Havana.
- Cuba lacks Venezuela’s vast natural resources, making the case of prioritizing political stability to extract revenues (and eventually hold elections) harder to sell. Cuba has significant reserves of nickel and cobalt and some oil exploration but not nearly at Venezuela’s scale. Its agricultural sector is in tatters and reviving sugar production would be opposed by U.S. farmers amid an already oversupplied global marketplace.
- It’s also unclear where the power lies in Havana; who could serve as the “Cuban Delcy Rodriguez”?
- Over 60 years of communist rule has restructured Cuba’s political and economic systems. Government officials, party members and the armed forces are indoctrinated and control key areas of the economy.
- Cuba doesn’t have a credible opposition to guide the path to democratization, if that were part of the Trump administration’s agenda. Unlike Venezuela, there are no elected opposition members and the island’s opposition forces are divided and isolated.
- Russia and China may take a more assertive stance to protect their interests and tame the Trump administration’s claim on the Western Hemisphere Direct military confrontation is unlikely, but Moscow and Beijing could deploy hybrid tactics or support local militias.
At the same time, a continuation of the “maximum pressure” campaign or ousting the regime risks massive social unrest and potentially a power vacuum that exacerbates regional insecurity and illegal migration.
How events will play out is unknown, but one thing is certain: Cuba presents a non-trivial political risk for Trump and a cautionary tale for U.S. regional partners increasingly concerned about spill-over effects and their own sovereignty.
Policy Contributing Writer Filipa Jorge is a principal at The Scowcroft Group, where she provides strategic risk advisory services on issues including Latin America, Europe, and BRICS+.
The Scowcroft Group is a Washington, D.C.-based international business advisory firm founded by the late Brent Scowcroft, former National Security Advisor to Presidents George H.W. Bush and Gerald Ford. Its principals generously provide Policy’s regular Letter from Washington and Scowcroft Group Snapshot posts.
