After launching what amounted to an invasion of Venezuela, President Donald Trump quickly signaled that Cuba would be next. Even as the United States remains mired in what is becoming a war of attrition with Iran, Trump has declared with striking confidence that he can take over Cuba at will. The boast has raised eyebrows internationally, but it is not without some basis in reality. The most pressing question is not whether a deal can be struck, but what happens after the ink dries.
Before the Venezuela operation commenced, Washington and Havana had already begun holding secret talks. The United States wanted Cuba to align with Trump's national security framework, a strategy premised on the idea that the Americas remain firmly within America's sphere of influence. Under this vision, regional resources should be allocated according to Washington's preferences, requiring Havana to sever its deep-seated dependencies on Beijing and Moscow. In return, Cuba would be permitted to keep its communist system intact. The immediate condition for this arrangement was the resignation of President Miguel Díaz-Canel. His departure would give Trump a narrative victory and a face-saving way to claim he toppled a left-wing government that had defied the United States for decades, ostensibly completing what no American president had managed in 65 years.
Once a preliminary understanding was reached, both sides used the cover of aCaribbean Community summit last month to hold a further secret meeting in Saint Kitts, one of Taiwan's diplomatic allies. Secretary of State Marco Rubio led the American delegation, while the Cuban side was represented by a grandson of former President Raúl Castro. Both governments initially denied the meeting had taken place before eventually acknowledging that contact had occurred. Although Rubio stated the talks produced no results, American participants indicated that a clear consensus had emerged. According to these outlines, Díaz-Canel would resign, Cuba would pursue economic liberalization with priority investment rights granted to American firms, political prisoners would be released, and the United States would ease certain embargo restrictions.
Cuba's willingness to compromise its foundational revolutionary principles is rooted in cold geography and even colder pragmatism. Beijing and Moscow are simply too far away to offer reliable protection, while the United States sits right on Cuba's doorstep. The Venezuela operation made it abundantly clear that Washington is willing to act militarily, and Trump's inherent unpredictability makes waiting out his administration a dangerous strategy. For Havana, regime survival is the ultimate priority.
Washington has tended to view Díaz-Canel as a hardliner, but he is more accurately described as a figurehead for Castro, a man without genuine power. Actual influence in Cuba rests with two primary forces. The first is the Castro family itself, a dynamic evidenced by Castro's grandson serving as the key negotiator with Rubio. The second is GAESA, the military-run commercial conglomerate that controls Cuba's tourism, logistics, ports, and infrastructure. Ideologically conservative but economically pragmatic, GAESA's leadership calculates that under a deal preserving the existing system, they will retain their political authority, protect their economic privileges, and secure first access to an influx of American investment. The incentives for the Cuban military elite to cut a deal are substantial.
This underlying dynamic explains why Trump feels confident enough to talk openly about taking Cuba. However, the most consequential objective for many hardliners — ending Cuban communism and achieving genuine regime change — is precisely what this arrangement fails to deliver. That glaring omission will generate a fierce backlash from anti-Castro Cuban American communities, particularly in the Miami area, as well as from democracy advocates inside Cuba and within the American legislative process itself. Congress has enacted multiple statutes restricting engagement with Havana, most notably the Cuban Liberty and Democratic Solidarity Act, which sets strict legal conditions for lifting sanctions. Trump himself added a layer of complexity to this process by redesignating Cuba as a state sponsor of terrorism during the final stretch of his first term.
By allowing the existing Cuban ruling class to remain in power, Trump may believe he is securing a quick, historic win. In practice, he risks crafting a diplomatic arrangement that cuts both ways. It is a deal that could severely alienate his own political base while failing to fundamentally transform Cuba. Ultimately, this half-measure could entangle Washington in a prolonged strategic dilemma in the Caribbean, not unlike the protracted conflict it now faces in Iran.
*The author is an associate professor at Chihlee University of Technology. （Related： Taiwan Seeks U.S. Manufacturer Help to Restart Nuclear Plants No. 2 and No. 3 ｜ Latest ）
