▶ Watch Video: Senior U.S. defense officials weigh military options in Cuba
Washington — As the U.S.-Iran war restarts following the collapse of the weeks-long ceasefire, senior Pentagon officials are also quietly eyeing another flashpoint much closer to home: Cuba.
Military planners have in recent weeks examined a range of options for possible action against the island, including an Army-led air assault involving thousands of U.S. soldiers to be carried out by the 101st Airborne Division, the only unit trained for such a task, according to multiple U.S. officials with knowledge of the discussions.
The officials, who spoke to CBS News under condition of anonymity to discuss national security matters, stressed that the briefings are not an indication that President Trump or the Pentagon have decided to carry out an operation.
Any operation against Cuba would confront the Pentagon with a significant problem because much of the U.S. military’s attention and some of its most valuable offensive capabilities are already committed elsewhere. Secretary of State Marco Rubio has emphasized that the U.S. prefers a diplomatic option for a transition to a new government led by technocrats and willing to make economic reforms. That process has stalled, despite tightening financial pressure around the Cuban military and its conglomerate GAESA, the sprawling, military-controlled holding company which the United States refers to as an $18 billion trust fund. In a July 11 statement, Rubio said that so far, the regime and its “corrupt elites” continue to refuse reform, instead “perpetuating their total control” and adherence to a “morally bankrupt Marxist ideology.”
The State Department announced that it has also tightened the financial vice around Cuba’s state-owned entities that “funnel revenue to the regime and paramilitary forces” that repress the Cuban people, including rapid response brigades.
Late last month, the U.S. military held a concept-of-operations briefing to discuss early-stage military planning options for select missions that could be carried out, the officials said. Such briefings are routinely developed by the Defense Department and combatant commands for a range of contingencies that examine mission objectives, the number of troops needed, the sequence of events, logistical considerations and associated risks.
The Pentagon has shifted aircraft, intelligence assets and other resources from other geographical regions to the Middle East to sustain operations against Iran. Officials who spoke to CBS News said that shifting the focus toward Cuba isn’t likely at the moment, given the restart of military operations against Iran last week.
Behind the scenes, the war with Iran has exposed some friction between President Trump and Hegseth, an Army veteran and former Fox News host, according to sources familiar with the matter. While Mr. Trump has at times praised Hegseth and various military operations during his second term, he has privately expressed frustration with the progress of Operation Epic Fury, believing the administration missed an opportunity to avert a dragged-out conflict earlier this year by rejecting an Iranian proposal to limit its nuclear program, the officials said.
Two U.S. officials told CBS News that Hegseth urged a more confrontational approach to Iran, despite reservations voiced by Gen. Dan Caine, the chairman of the Joint Chiefs of Staff, leaving the president increasingly dissatisfied as the military campaign has become more protracted and complicated than originally anticipated when the war began back in February.
Over the course of the U.S.-Israel-led war against Iran, Mr. Trump has been irritated by both Hegseth and Caine when they raised the limitations of military operations. Some in the Defense Department and on the interagency team have also expressed frustration with Navy Adm. Brad Cooper, the commander of U.S. Central Command, grumbling that he oversold what the military could accomplish against Iran, one of the sources said.
Anna Kelly, a White House spokeswoman, said 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 the recent U.S. strikes against Iran prove the U.S. “can attack anywhere, anytime, and Iran can do nothing about it.”
Acting Pentagon press secretary Joel Valdez said, “We do not comment on hypothetical military operations,” and added that the department also wouldn’t comment on Hegseth’s private conversations with Mr. Trump.
Cuba has presented new security challenges. CBS News previously reported that Cuba had acquired attack drones of unknown origin. During a June 10 visit to the U.S. Naval base at Guantanamo Bay, Hegseth indirectly acknowledged the possibility of a threat to that installation.
“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.
Hegseth acknowledged the U.S. was presenting military options to Mr. Trump, but offered the possibility of a more peaceful relationship, saying the U.S. hopes to soon be “a friend of the leadership of the government of Cuba.”
CBS News reported in May that U.S. intelligence officials have been assessing how Cuba would respond to possible U.S. military action, as the Trump administration accused Havana of strengthening ties with Russia, China and Iran. The intelligence community’s 2026 annual threat assessment largely portrays Cuba as an enabling environment for larger geopolitical competitors, rather than as an independent strategic threat. Notably, the March assessment doesn’t identify Cuba itself as possessing military capabilities that materially threaten the U.S. or describe Havana as an independent driver of instability.
In May, CIA Director John Ratcliffe traveled to Havana for a rare meeting with senior Cuban officials, using the visit to deliver a message that the U.S. was prepared to expand economic and security engagement with Cuba if Havana “makes fundamental changes.”
But Ratcliffe also brought along one of the operators who was involved in the U.S. mission to capture then-Venezuelan leader Nicolás Maduro in January, making a point of introducing the paramilitary leader to the Cubans as the one who had killed their people in Venezuela, several people familiar with the trip told CBS News.
Days after the visit, the Justice Department indicted 95-year-old former leader Raul Castro and five others on charges dating back to the 1996 shootdown of two U.S. planes. That indictment has led to speculation that Castro would be arrested in an operation similar to the snatch and grab of Maduro. Multiple sources told CBS News that the preference would be for the Castro family to depart the island of their own accord, and nodded to the Trump administration’s meetings with Castro’s grandnephew Raulito.
The administration’s confrontation with Cuba did not emerge overnight. Over the past 18 months, the White House has steadily dismantled the limited engagement pursued under former Presidents Joe Biden and Barack Obama and replaced it with a campaign of economic, diplomatic and legal pressure that has isolated Havana and deprived its security apparatus of revenue in an effort to force political change.
Cuba policy since Trump’s return to office
Hours after returning to office in January 2025, Mr. Trump reversed one of Biden’s final foreign policy decisions by restoring Cuba’s designation as a state sponsor of terrorism, a move that again restricted Cuba’s access to international finance and signaled a return to the “maximum pressure” strategy of Mr. Trump’s first term.
The Trump administration expanded that approach when Rubio reinstated restrictions on business transactions with Cuba’s military-controlled conglomerate, GAESA, arguing that the armed forces—not Cuba’s 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 trying to discredit thousands of Cuban doctors working around the world while also cutting off a critical source of income to the island country.
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 that expanded restrictions on travel, remittances and financial transactions, while strengthening enforcement of the embargo.
The campaign escalated further 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, marked by fuel shortages, blackouts and protests. Cuban officials blamed U.S. sanctions, while the Trump administration pointed to internal mismanagement.