What is Trump’s Next Move in Cuba?
By Sierra Knoch | April 30, 2026
What is Trump’s next move in Cuba? As the Iran Operation is wrapping up, all eyes are turning to the small island nation 90 miles off the coast of the US as Trump and his team have repeatedly hinted that their attention will be turning to Cuba next as they take on America’s longtime enemies that grew too powerful under Biden’s absentee Presidency.
Let’s try to unpack America First foreign policy and the administration’s strategic approach to the island nation. What may be emerging is a clear vision: President Trump is applying sustained, innovative pressure on the Cuban regime, leveraging economic tools, key allies like Secretary of State Marco Rubio, and a personal commitment to ending 67 years of communist rule.However, experts have highlighted why Cuba represents one of Trump’s biggest challenges yet — and greatest opportunities. While the administration has scored major wins elsewhere in Latin America, Cuba’s entrenched regime, propped up by alliances with China, Russia, and residual Venezuelan support, demands a tailored strategy.
Current Maximum Pressure Campaign
Since taking office in 2025, the Trump administration has escalated actions against Havana:
Oil Blockade and Sanctions: Tightened restrictions on oil shipments (Cuba relies heavily on imports) and over 240 new sanctions aimed at crippling the regime’s economy.
Executive Actions: Trump declared Cuba a national security threat and cut off money flows.
Diplomatic Maneuvers: Secret talks reportedly involving Rubio and Cuban officials, framed around potential economic openings in exchange for reforms.
Trump has publicly predicted Cuba will “fall pretty soon,” positioning it as a follow-on priority after successes against threats like Iran. The goal isn’t necessarily immediate military action but creating conditions for internal change or negotiated transition — what some describe as a “friendly takeover” or slow shift toward liberalization. Although Trump has stated he may use military actions as well depending on how things go. Expert Mercedes Schlapp recently outlined an America First approach rooted in strength, not endless wars but warned that the Cuba project could be a longer term problem for the administration.
She laid out Trump’s options and his approach highlighting key themes like:
Creative Pressure: Beyond blunt sanctions, the administration is using targeted tools to isolate the regime economically and diplomatically, making strides toward long-overdue transformation.
The Monroe Doctrine Updated (“Donroe Doctrine”): Latin America turning toward the U.S. through strong alliances, free from Chinese and Russian meddling.
Why It Matters for Americans:
Fighting communism abroad prevents it from gaining footholds that threaten U.S. borders, migration, and security. A free Cuba could become a prosperous partner rather than a failing state exporting instability.
Schlapp also expressed confidence that if change will happen at all in Cuba President Trump is the one who can achieve it, working with Rubio who has proven to be an effective planner and diplomat when it comes to matters in Latin America.
Looking Ahead: Why its more complicated than people realize
Analysts see 2026 as potentially pivotal. The strategy combines economic choke points with back-channel diplomacy, aiming for market reforms, leadership shifts, and eventual free elections — all while avoiding the costs of direct intervention. Challenges remain: humanitarian impacts, regime resilience, and regional reactions. Yet the momentum is clear — Cuba’s leaders are watching developments in Venezuela and Iran closely. But there are key items that Trump needs to secure from the Cuban regime in order to move forward with any real change. Schlapp outlined these priority items including: change in Presidential leadership, ending the Castro family’s hold on political power in Cuba, and ending oppression of the Cuban people. In Cuba, the only economic opportunities are for those in military or intelligence roles that were previously exported to places like Venezuela. Also, there are no organized political opposition parties in Cuba which poses problems for creating any type of transitional government or holding elections. Schlapp says, “You are really almost starting from scratch in Cuba.”
As Schlapp stressed in the conversation, the fight for a free Cuba is decades in the making. However, with Trump at the helm, creative pressure, and unwavering resolve, freedom for Cuba may not come overnight, but under this administration, the pressure is building — and the regime knows its time is limited.
