President Donald Trump has signaled plans for a U.S. takeover of Cuba, raising questions about the feasibility and potential consequences of such an action. Trump made the announcement following the start of military conflict with Iran, stating that “on the way back” from Iran, the United States would assume control of Cuba “almost immediately.” As he faces political pressures ahead of the upcoming autumn elections, the administration appears eager for a foreign policy success.

Cuba, governed by a communist regime for 67 years through 13 U.S. presidencies, remains a tightly controlled state led primarily by Raúl Castro, who at 95 still wields influence. The government has resisted political and economic reforms, maintaining strict limits on free enterprise and civil liberties. Its economy, once supported by Soviet subsidies and later Venezuelan oil, has sharply declined in recent years. Reports indicate widespread electricity blackouts lasting up to 22 hours daily, significant reductions in agricultural output, and the collapse of key export industries such as sugar, tobacco, and coffee. Tourism, a critical revenue source, has declined sharply as airlines have curtailed flights due to fuel shortages.

Cuban Americans, a key segment of Trump’s political base, largely favor military intervention, according to a Miami Herald poll. Many oppose any form of economic engagement that might sustain the current regime. Interior Secretary Doug Burgum has stated that Cuba’s economy will not improve “as long as the people who are in charge of it now remain in power,” highlighting the dominant role of Gaesa, a military-controlled conglomerate responsible for approximately 70 percent of Cuba’s economy.

Between 2019 and 2024, Cuba’s economy shrank by an estimated 11 percent, and over 1 million Cubans—approximately 10 percent of the population—have fled the country between 2022 and 2023. The Trump administration argues that the country, though weakened, still poses a threat to U.S. national security, especially given Havana’s continuing ties with Russia and China, including reported use of the island for military surveillance. Despite Cuba’s diminished military capabilities, including a reduced army and a small, outdated air force, the regime retains control and influence.

However, Cuba’s political landscape remains deeply challenging. A brief uprising in March saw a mob attack the Communist Party headquarters, but the incident was isolated and quickly suppressed. The population is largely described as politically fragmented and wary, with limited experience in civic collaboration. Analysts note that a peaceful transition to democracy appears unlikely under current conditions.

Trump’s assurances that the regime is ready to fall and his vivid descriptions of a symbolic U.S. aircraft carrier blockade illustrate a confidence that has drawn skepticism from experts who warn of the complex realities on the ground. While the United States possesses leverage over Havana, the risks of unintended consequences and the absence of a clear path forward raise questions about the wisdom and practicality of declaring or attempting a swift takeover of Cuba.