US pressure on Cuba intensifies as analysts see regime at its weakest in decades

US political and security indicators toward Cuba have escalated markedly in recent months, according to The Hill, as conservative circles in Washington increasingly assess that the Cuban regime is passing through one of its most vulnerable phases in decades. The assessment comes amid crushing economic pressures, tightened sanctions, and a surge in US military surveillance and intelligence activities near the island.

The newspaper argues that recent US moves reflect a transition of the Cuban file from a phase of political containment to one of multi-tool strategic pressure. This shift follows Washington’s intensification of aerial reconnaissance and surveillance operations, as well as the launch of military drills incorporating artificial intelligence and unmanned systems near Cuban shores.

Military Drills and New Command Structure

Over the past weeks, the United States conducted strategic exercises in Florida that focused on integrating AI and drone systems into military operations across the Americas. The drills were widely seen as a direct message to Havana. For the first time, the exercises unveiled the Autonomous Warfare Command under US Southern Command, a system relying on low-cost autonomous and semi-autonomous platforms—including drones and smart surveillance stations—to counter regional threats.

US media reports indicate that Washington has carried out dozens of reconnaissance and intelligence-gathering sorties off the Cuban coast since February, using surveillance aircraft and specialized drones to collect signals intelligence and monitor military movements and communications. Analysts view this activity as reflecting Washington’s growing interest in Cuba’s security and military infrastructure, particularly amid US concerns over expanding security cooperation between Havana and US adversaries.

Trump’s Rhetoric and Military Posturing

President Donald Trump has sharpened his tone toward the Cuban regime, stating that Havana could be “the next phase” following US escalation against Iran, as The Hill reported citing conservative US media. According to those statements, Washington is considering reinforcing its military presence near the island, including the possible deployment of the aircraft carrier USS Abraham Lincoln to the region to “deter the Cuban regime.” This marks a shift in US rhetoric from economic pressure to the implicit threat of military deterrence.

The newspaper also noted that Trump revived predictions by political analyst Mark Thiessen, who spoke of the possibility of visiting a “free Havana” before the end of his second presidential term—a symbolic reference to the potential for regime change on the island. Some conservative circles in Washington, per The Hill, invoke historical precedents of US interventions in Latin America, from Operation Just Cause in Panama in 1990 to recent developments involving Venezuelan President Nicolás Maduro, as indicators of mounting US pressure on hostile regimes in the region.

Economic Sanctions Target the Military’s Economic Empire

On the economic front, the US administration has expanded sanctions on Cuba, declaring that the Cuban regime poses an “unusual and extraordinary threat” to US national security. The Hill reported that the sanctions now target the GAESA conglomerate, the backbone of the Cuban military establishment’s economic empire and the Castro family’s interests. GAESA controls vast sectors including tourism, trade, financial services, and real estate.

Economic circles view the targeting of GAESA as carrying implications beyond traditional sanctions, aiming to undermine the ruling elite’s main funding sources and reduce the regime’s ability to manage its internal economic networks. These pressures come as Cuba suffers a severe economic crisis marked by fuel and food shortages, currency devaluation, and rising emigration rates, compounding social and political strain on the government.

US Secretary of State Marco Rubio asserted that Cuba’s economic crisis is directly linked to the nature of the existing political system. “The Cuban economy will not change unless the system of governance changes,” Rubio was quoted as saying by The Hill, adding that international investors will not pour billions of dollars into a communist economy suffering structural imbalances and weak economic management. Rubio’s remarks reflect a growing trend within the US administration to tie economic opening in Cuba to broader political reforms, as some Washington circles increasingly bet on the possibility of internal transformation under accumulated pressure.

Internal Crackdown and Waning International Support

In response, Cuban authorities have intensified security mobilization and internal surveillance, amid reports of growing concern within state institutions over the potential for social unrest or rising popular protests. The Hill noted the expansion of military training programs for civilians, tighter media and security controls, and political mobilization campaigns urging citizens to pledge loyalty to the regime.

Efforts to rally political support for Cuba have shown a marked decline, according to the newspaper. A leftist gathering held in Barcelona, Spain, drew limited participation, while clear official backing was confined to the governments of Brazil, Mexico, and Spain.

Observers argue that the combination of increased US reconnaissance activities, tightened economic sanctions, and escalating political rhetoric in Washington all point to a new phase of compounded pressure on the Cuban regime, at a time when the island faces one of its most complex economic and political crises in decades.