President Donald Trump said on Tuesday that a diplomatic agreement with Cuba is possible and that resolving the issue will not be difficult [1].

This shift toward potential diplomacy comes as Cuba faces severe shortages, creating a tension between the administration's public openness to a deal and its continued use of sanctions to pressure the island.

Speaking during a press briefing in Miami, Florida, Trump said the U.S. does not want to see Cuba suffer from these shortages and wants to help the island [1], [2]. He said that the Cuban government has been reaching out to the United States, stating, "Cuba nos está llamando" [3].

Trump also addressed the influence and presence of the Cuban diaspora in Florida. He said he has "gran estima" for the Cuban community, specifically those living in Miami [1].

Despite these comments, the administration's approach remains contradictory. While Trump said, "Resolver el tema de Cuba no será difícil" [2], reports indicate that the U.S. is simultaneously increasing pressure on the island [4].

Further complicating the public narrative are reports of private diplomacy. Some sources indicate that Trump has been engaging in secret conversations with a member of the Castro family, even as he maintains a public stance of strict sanctions [5].

These developments occurred on May 19, 2026 [1], marking a moment where the U.S. executive branch is balancing humanitarian concerns, diplomatic outreach, and a long-standing policy of economic isolation.

"Cuba nos está llamando."

The administration is employing a 'carrot-and-stick' strategy, combining the threat of increased sanctions with the promise of diplomatic relief. By publicly acknowledging Cuba's internal crises and the desire for an agreement, the U.S. may be attempting to leverage Cuba's economic instability to secure specific political concessions before formally easing restrictions.