Washington — Senior Pentagon officials have been quietly examining a range of military options for potential action against Cuba, including an Army-led air assault involving thousands of U.S. soldiers. The 101st Airborne Division, the only unit trained for such a task, has been considered for this operation, according to multiple U.S. officials with knowledge of the discussions.
These officials, who spoke anonymously due to the sensitivity of national security matters, emphasized that these briefings do not indicate a decision by President Trump or the Pentagon to carry out such an operation. Any significant military action against Cuba would present a challenge for the Pentagon, as much of the U.S. military's attention and many valuable offensive capabilities are currently committed elsewhere, particularly following the restart of military operations against Iran last week.
Secretary of State Marco Rubio has consistently advocated for a diplomatic solution, preferring a transition to a new Cuban government led by technocrats willing to implement economic reforms. However, this diplomatic process has stalled, despite increasing financial pressure on the Cuban military and its sprawling conglomerate, GAESA. The United States refers to GAESA, a military-controlled holding company, as an $18 billion trust fund. In a July 11 statement, Rubio asserted that the Cuban regime and its "corrupt elites" continue to reject reform, instead "perpetuating their total control" and adherence to a "morally bankrupt Marxist ideology."
The State Department has also tightened financial restrictions on Cuba's state-owned entities, which it claims "funnel revenue to the regime and paramilitary forces" that repress the Cuban people, including rapid response brigades.
Late last month, the U.S. military conducted a concept-of-operations briefing to discuss early-stage planning options for select missions. Such briefings are a routine practice by the Defense Department and combatant commands to examine mission objectives, troop requirements, event sequences, logistical considerations, and associated risks for various contingencies.
The Pentagon has redirected aircraft, intelligence assets, and other resources from other geographical regions to the Middle East to support operations against Iran. Officials indicate that shifting focus toward Cuba is unlikely at the moment, given the renewed military engagement with Iran.
Behind the scenes, the conflict with Iran has reportedly exposed friction between President Trump and Hegseth, an Army veteran and former Fox News host. Sources familiar with the matter state that while Mr. Trump has publicly praised Hegseth and various military operations, he has privately expressed frustration with the progress of Operation Epic Fury. The President reportedly believes the administration missed an opportunity earlier this year to avert a prolonged conflict by rejecting an Iranian proposal to limit its nuclear program.
Two U.S. officials noted that Hegseth urged a more confrontational approach to Iran, despite reservations voiced by Gen. Dan Caine, the chairman of the Joint Chiefs of Staff. This left the president increasingly dissatisfied as the military campaign, which began in February, became more protracted and complicated than initially anticipated. Mr. Trump has reportedly been irritated by both Hegseth and Caine when they raised limitations of military operations. Some within the Defense Department and the interagency team have also expressed frustration with Navy Adm. Brad Cooper, the commander of U.S. Central Command, alleging he oversold the military's potential achievements against Iran.
White House spokeswoman Anna Kelly countered these claims, stating the president "has been extraordinarily proud" of Hegseth and Cooper's leadership "throughout Operation Epic Fury, which completely destroyed Iran's ballistic missiles, production facilities, navy, air defenses, and more." She added that recent U.S. strikes against Iran demonstrate the U.S. "can attack anywhere, anytime, and Iran can do nothing about it." Acting Pentagon press secretary Joel Valdez declined to comment on "hypothetical military operations" or Hegseth's private conversations with Mr. Trump.
In May, U.S. intelligence officials were assessing Cuba's potential response to U.S. military action, as the Trump administration accused Havana of strengthening ties with Russia, China, and Iran. The intelligence community's March 2026 annual threat assessment largely portrays Cuba as an enabling environment for larger geopolitical competitors, rather than an independent strategic threat. The assessment notably does not identify Cuba as possessing military capabilities that materially threaten the U.S. or describe Havana as an independent driver of instability.
Also in May, CIA Director John Ratcliffe traveled to Havana for a rare meeting with senior Cuban officials. During his visit, Ratcliffe delivered a message that the U.S. was prepared to expand economic and security engagement with Cuba if Havana "makes fundamental changes." Intriguingly, Ratcliffe brought along one of the operators involved in the January U.S. mission to capture then-Venezuelan leader Nicolás Maduro, introducing the paramilitary leader to the Cubans as the one who had killed their people in Venezuela, according to several people familiar with the trip.
Days after Ratcliffe's visit, the Justice Department indicted 95-year-old former leader Raul Castro and five others on charges stemming from the 1996 shootdown of two U.S. planes. This indictment has fueled speculation about Castro's potential arrest in an operation similar to the "snatch and grab" of Maduro. Multiple sources indicated a preference for the Castro family to depart the island voluntarily, with some noting the Trump administration's meetings with Castro's grandnephew Raulito.
The administration's confrontational approach to Cuba has developed over 18 months, during which the White House systematically dismantled the limited engagement policies pursued under former Presidents Joe Biden and Barack Obama. This was replaced with a campaign of economic, diplomatic, and legal pressure designed to isolate Havana and deprive its security apparatus of revenue, aiming to force political change.
The Trump administration expanded this approach when Rubio reinstated restrictions on business transactions with GAESA, arguing that Cuba's armed forces, not its private sector, control much of the island's hard-currency economy. Weeks later, the State Department broadened visa restrictions targeting Cuba's overseas medical missions, accusing Havana of exploiting doctors and nurses through a state-run labor export system that Cuban officials insist is voluntary. Deputy Foreign Minister Carlos Fernandez de Cossio told The Associated Press in June that the Trump administration was attempting to discredit thousands of Cuban doctors working globally while also cutting off a critical source of income for the island nation.
Despite rising tensions, limited cooperation continued, including Cuba's acceptance of U.S. deportation flights under existing migration agreements. By mid-2025, the Trump administration formalized its approach through a new National Security Presidential Memorandum, which expanded restrictions on travel, remittances, and financial transactions, while strengthening enforcement of the embargo. The campaign further escalated earlier this year when Mr. Trump declared Cuba an "unusual and extraordinary threat" and extended sanctions to foreign governments and companies supplying the island with oil. Additional actions included sanctions on senior Cuban officials, and penalties targeting Cuban President Miguel Diaz-Canel and other top figures.
These measures coincided with a worsening economic crisis in Cuba, characterized by fuel shortages, blackouts, and protests. Cuban officials have attributed these issues to U.S. sanctions, while the Trump administration has pointed to internal mismanagement.
"It would be unwise for the government of Cuba to try to procure or get access to the types of weapons that could reach this base or the American homeland. They would be inviting the kind of confrontation not only do they not want, but they could not stand," he vowed.
Cuba and the U.S. have a longstanding dispute over the facility — after the 1959 Cuban Revolution, Fidel Castro refused to cash the checks, claiming the lease, signed in 1903, is invalid.
