Washington — As the U.S.-Iranian war resumes after a week-long cease-fire broke down, senior Pentagon officials are also quietly eyeing another flashpoint much closer to home: Cuba.
Military planners in recent weeks have explored a number of options for possible action against the island, including an Army-led air assault involving thousands of US troops to be carried out by the 101st Airborne Division, the only unit trained for such a task, according to multiple US officials with knowledge of the discussions.
The officials, who spoke to CBS News on condition of anonymity to discuss national security issues, stressed that the briefings were not an indication that President Trump or the Pentagon had decided to conduct the operation.
Any operation against Cuba would present the Pentagon with a major challenge because much of the US military’s attention and some of its most valuable offensive capabilities are already focused elsewhere. Secretary of State Marco Rubio emphasized that the US prefers the diplomatic option of transition to a new government led by technocrats and a desire to carry out economic reforms. That process has stalled despite mounting financial pressure around the Cuban military and its conglomerate GAESA, a vast military-controlled holding company that the United States calls an $18 billion trust fund. Already July 11 statementRubio 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 financial sanctions around Cuban state-owned enterprises that “direct revenues to the regime and paramilitary forces” that repress the Cuban people, including emergency response teams.
Late last month, the U.S. military held a concept of operations briefing to discuss early-stage military planning options for individual missions that could be undertaken, officials said. Such briefings are routinely developed by the Department of Defense and combatant commands for a range of contingencies that examine mission objectives, number of troops required, sequence of events, logistics and associated risks.
The Pentagon has shifted aircraft, intelligence and other resources from other geographic regions to the Middle East to support operations against Iran. Officials who spoke to CBS News said a shift in focus to Cuba is unlikely at this point, given last week’s resumption of hostilities against Iran.
Behind the scenes, the war with Iran has exposed some friction between President Trump and Hegsett, an Army veteran and former Fox News anchor, according to sources familiar with the matter. While Mr. Trump has at times praised Mr. Hegseth and various military operations during his second term, he has privately expressed frustration with Operation Epic Fury, suggesting the administration missed an opportunity to avert a protracted conflict earlier this year by rejecting Iran’s offer to curb its nuclear program, officials said.
Two U.S. officials told CBS News that Hegseth called for a more confrontational approach to Iran despite reservations from Gen. Dan Cain, the chairman of the Joint Chiefs of Staff, leaving the president increasingly unhappy that the military campaign has become longer and more complex than originally expected when the war began in February.
In the US-Israeli-led war against Iran, Mr Trump has been irked by both Hegseth and Kaine as they lifted restrictions on military operations. Some in the Defense Department and on the interagency team also expressed frustration with Navy Admiral Brad Cooper, the commander of U.S. Central Command, who grumbled that he had oversold what the military could achieve against Iran, one of the sources said.
Anna Kelly, a White House press secretary, said the president was “incredibly proud” of Hegsett and Cooper’s leadership “during Operation Epic Fury, which completely destroyed Iran’s ballistic missiles, manufacturing facilities, navy, air defenses and more.” She added that recent US strikes on Iran prove that the US “can attack anywhere and anytime, and Iran can’t do anything about it.”
Acting Pentagon spokesman Joel Valdez said, “We don’t comment on hypothetical military operations,” adding that the department also would not comment on Mr. Hegsett’s private conversations with Mr. Trump.
Cuba posed new security challenges. CBS News earlier reported that Cuba has acquired attack drones of unknown origin. During a June 10 visit to the US naval base at Guantanamo Bay, Hegsett implicitly acknowledged the possibility of a threat to the facility.
“It would be unwise for the Cuban government to attempt to procure or gain access to the types of weapons that could reach this base or the American homeland. They would cause such a confrontation, which they not only do not want, but also cannot endure,” he promised.
Cuba and the US have a long-standing dispute over the facility – after the 1959 Cuban Revolution, Fidel Castro refused to cash the checks, saying the lease, signed in 1903, was invalid.
Hegseth acknowledged that the US was presenting Mr Trump with military options, but suggested the possibility of a more peaceful relationship, saying the US hoped to soon become “friends with the leadership of the Cuban government”.
CBS News reported in May that US intelligence officials were evaluating how Cuba will respond to possible US military action as the Trump administration has accused Havana of strengthening ties with Russia, China and Iran. 2026 Intelligence Community Yearbook threat assessment largely portrays Cuba as an enabling environment for larger geopolitical rivals rather than an independent strategic threat. Notably, the March assessment does not identify Cuba itself as possessing a military capability that significantly threatens the United States, nor does it describe Havana as an independent factor in instability.
In May, CIA Director John Ratcliffe visited Havana for a rare meeting with senior Cuban officials, using the visit to convey the message that the U.S. is willing to expand economic and security cooperation with Cuba if Havana “makes fundamental changes.”
But Ratcliffe also took one of them with him operators who participated in the U.S. mission to capture then-Venezuelan leader Nicolás Maduro in January, making a point of branding the paramilitary leader to Cubans as the one who killed their people in Venezuela, several people familiar with the trip told CBS News.
A few days after the visit of the Ministry of Justice accused 95-year-old former leader Raul Castro and five others on charges in 1996 downing of two American planes. The accusation led to speculation that Castro would be arrested in an operation similar to Maduro’s kidnapping and capture. Multiple sources told CBS News that it would be most desirable for the Castro family to leave the island on their own accord, a nod to the Trump administration’s meeting with Castro’s great-nephew Raulita.
The administration’s confrontation with Cuba did not arise immediately. Over the past 18 months, the White House has steadily dismantled the limited engagement under former presidents Joe Biden and Barack Obama, replacing it with a campaign of economic, diplomatic and legal pressure that has isolated Havana and deprived its security apparatus of revenue in an attempt to force political change.
Cuba policy after Trump’s return to office
Hours after returning to office in January 2025, Mr. Trump inverted one of Biden’s latest foreign policy decisions, restoring Cuba’s status as a state sponsor of terrorism, again limiting Cuba’s access to international finance and marking 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 military, not Cuba’s private sector, controls much of the island’s hard-currency economy. A few weeks later, the State Department expanded visa restrictions targeting Cuba’s foreign medical missions, accusing Havana of exploiting doctors and nurses through the government’s labor export system, which Cuban officials say is voluntary.
Deputy Foreign Minister Carlos Fernandez de Cosio told The Associated Press said in June that the Trump administration was trying to discredit thousands of Cuban doctors working around the world while cutting off an important source of income for the island nation.
Despite rising tensions, limited cooperation continued, including Cuba’s acceptance of US deportation flights under existing migration agreements. By mid-2025, the Trump administration formalized its approach through a new Presidential National Security Memorandum that expands restrictions on travel, money transfers 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 on foreign governments and companies that supply the island with oil. Additional actions included sanctions against high-ranking Cuban officials and executions targeting Cuban President Miguel Diaz-Canel and other dignitaries.
The measures coincided with a worsening economic crisis in Cuba marked by fuel shortages, blackouts and protests. Cuban officials have blamed US sanctions, while the Trump administration has pointed to domestic mismanagement.