Can Donald Trump secure a deal with Cuba? | The Economist

Proposed Deal Mechanics

• The proposed framework requires the Cuban regime to present a credible, multi-party free election plan as a condition for economic relief.
• Specific concessions under consideration include lifting the oil embargo and the broader trade blockade.
• Leadership change within Cuba is contingent upon the administration securing a political roadmap Marco Rubio can sell to the Cuban-American voting bloc.
• The strategy mirrors a transactional approach similar to that attempted with Venezuela, prioritizing tangible moves over ideological purity.

Political Dynamics in Florida

• Florida has shifted from a swing state to a solidly Republican ("red") state, altering the political calculus for both parties.
• Historically, 1.2 to 1.5 million Cuban-Americans in Florida exerted disproportionate influence, preventing presidents from unilaterally lifting the embargo.
• Congressional hardliners passed strict laws codifying the need for legislative approval to lift the embargo, creating a structural barrier.
• Polling data indicates a generational divide: the younger Cuban-American generation became more open to embargo liberalization under Obama (2014), whereas rhetoric from the Trump administration (post-2017) shifted the community back toward hardline positions.

Key Figures and Stances

• Marco Rubio and Donald Trump are identified as the only figures capable of promising a long-term timeline that would satisfy Cuban-American voters.
• Former Congressman Joe Garcia argues that Cuban-Americans, largely dependent on government support ("on the dole"), will accept almost any deal ("doesn't matter what that croqueta looks like") that delivers progress.
• Garcia asserts that the Cuban regime itself is the primary obstacle preventing a deal that has been "offered which is damn good for everyone concerned."

Economic and Strategic Implications

• A potential deal could allow the Cuban regime to remain in power while facilitating economic openings necessary to supply the island.
• The administration's goal is to maintain the regime's existence in exchange for economic liberalization rather than immediate regime change.

Skepticism Regarding Implementation

• Critics warn that Donald Trump operates as a "crony capitalist" whose deals may extend contracts to friends rather than foster genuine, slow-motion economic reform.
• There is a high risk of the deal being used as a publicity event that lacks the consistent, long-term follow-up (months to years) required for a complex political transition.
• Past records show a lack of adherence to long-term plans, with a tendency to abandon complex initiatives after short-term gains.

Divergent Optimism Levels

• One participant argues that even a "shabby" or "cronyish" deal is preferable if it successfully dismantles the "decrepit, utterly stubborn" current regime.
• Conversely, another view holds that the lack of ideological nuance and the "attention span" of the current leadership make successful execution unlikely.
• The consensus suggests that while the opportunity for a transaction exists, the complexity of the required political transition poses a significant execution risk.