June 2, 2026

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The U.S. is Setting its Sights on Cuba

(AP Photo/Ramon Espinosa)

On Friday, the head of the U.S. Southern Command (SOUTHCOM), General Francis L. Donovan, met with numerous Cuban military commanders in a rare engagement about operational readiness and perimeter security at the U.S.’ Naval Station at Guantánamo Bay. The meeting followed just a week after a recent report was released by Axios, in which the outlet obtained leaked, classified intelligence detailing how Cuba acquired over 300 drones from Russia and Iran with a plan to attack the U.S. military installation at Guantánamo, U.S. military assets in the Caribbean, and even Key West, just under 100 miles from the shores of Cuba.

Reports of Cuba’s expanding drone fleet and designs of an attack come after months of the U.S. modifying and seeking justification to escalate its pressure campaign against Cuba. In January 2026, the Trump administration introduced an energy embargo against Cuba, cutting off oil shipments, threatening tariffs against any country that shipped it supplies, and interdicting vessels carrying energy supplies into Cuban waters. The economic pressure campaign has had a resounding effect, exacerbating an already dire financial crisis on the island. Cubans have faced days-long electricity blackouts, long bread lines, glacial transportation systems, and dwindling food and medicine supply. The healthcare system has particularly become affected — already challenged by the lack of access to medicine — with emergency service vehicles grounded due to the lack of fuel. The cost of basic necessities has outsized the average Cuban’s monthly salary of $14.46. Barbers even reportedly began offering free haircuts as a response to the economic crisis.

Trump administration officials sought to capitalize upon Cuba’s economic crisis through diplomacy with the Castro government, signaling incentives in exchange for political reforms. On February 26, Secretary of State Marco Rubio’s team reportedly met with the grandson of Raúl Castro — a close aide and overseer of the military-operated Grupo de Administración Empresarial S.A. (GAESA) that monopolizes between 40 percent and 70 percent of the Cuban economy — to discuss the option of potentially slowing sanctions in exchange for behavioral change: economic and democratic reforms. Secretary Rubio remarked at the conference that Cuba’s economic model was broken and signaled U.S. support if the government undertook change: “… if they want to make those dramatic reforms that open the space for both economic and eventually political freedom for the people of Cuba, obviously the U.S. would love to see that. We’d be helpful.”

The administration’s approach to Cuba, however, shifted both in tone and strategy in early spring. President Trump began making public statements that Cuba was “next” in a March summit in Miami and that the U.S. would be taking over “almost immediately” later in May, raising questions about whether the administration would seek to replicate its strategy of regime change that it conducted in Venezuela earlier this year. Like the lead-up to the U.S.’ Venezuela intervention, the Trump administration authorized an incremental naval military buildup through surveillance aircraft and the USS Nimitz — an aircraft carrier with fighter jets, guided-missile destroyers, and radar-jamming equipment — on May 21, according to POLITICO. It is also widely anticipated that the USS Kearsarge could soon arrive off the coast of Cuba, an amphibious assault vessel that has the capacity to transport up to 2,500 Marines. SOUTHCOM has also increased its tempo of training in nearby locations such as Key West, launching a new Autonomous Warfare Command that includes counter-drone operations and other unmanned platforms. Last week, the U.S. Department of Justice indicted former Cuban President Raúl Castro on four counts of murder for the downing of two civilian planes operated by U.S. nationals in 1996, something that the Trump administration could present as cause for intervention, mimicking U.S. charges against Maduro for narco-terrorism and trafficking. However, unlike in Venezuela, the Trump administration has added an additional component: an open intelligence-driven pressure campaign against Cuba through the Central Intelligence Agency (CIA).

There is a strong historical precedent of U.S.-sponsored coups and paramilitary operations by way of its intelligence services in Latin America, particularly in Cuba. However, these operations were clandestine, while the Trump administration has utilized its intelligence capacity — particularly the threat of launching a revolutionary overthrow of Cuba’s communist regime — out in the open. On May 15, CIA Director John Ratcliffe made a rare, unannounced appearance in Havana to meet with both Raúl Castro’s grandson and Cuban intelligence to speak about the lack of progression with political and economic reforms. Reportedly, Ratcliffe brought along a paramilitary officer who served as a key operator in the U.S. decapitation strike, “Operation Absolute Resolve,” against Cuba’s former ally, Venezuelan President Nicolás Maduro, a development that the Cuban delegation interpreted as a warning of potential intervention. Four days later, Trump remarked that the CIA has “a lot of people in Cuba” and that the U.S. was working to help “free up Cuba.”

The deepened U.S. intelligence footprint has also been flagged in neighboring Mexico, another country where the Trump administration has threatened interference amidst rising tensions over cartel networks and instability. In March, the CIA reportedly offered actionable intelligence to Mexican authorities that helped identify the location of the notable drug kingpin and founder of the Jalisco New Generation Cartel (CJNG) cartel, Nemesio Oseguera Cervantes ‘El Mencho’. Later in April, Mexican police reported that two CIA operatives were killed in a car crash in Chihuahua following their participation in a methamphetamine laboratory raid in El Pinal, without the knowledge of the Mexican government and no accreditation to operate in counter-cartel operations. That next month, reports from CNN surfaced that the CIA had been involved in planning and executing a car bomb attack on Sinaloa leader Francisco Beltrán ‘El Payín’, citing documents released from the Attorney General of Mexico, though denied by the CIA.

As the U.S. considers a strategy against its southern neighbors, the Trump administration has increasingly relied upon its intelligence agencies, even publicly touting them as a pressure tactic. However, while the U.S. weighs its options, the economic situation in countries like Cuba continue to worsen, creating increasing instability in lieu of U.S. military intervention and the potential for a migrant crisis emanating from the island country. Regardless of whether the U.S. intervenes, the downward spiral sparked by governmental mismanagement, economic pressure, and the threat of military intervention in Cuba may unravel its security landscape on its own, creating a different challenge that the Trump administration may not anticipate.