Pentagon Assembles Forces Near Cuba, Awaits Trump Order to Act

The Pentagon has spent months positioning troops and military assets in the Caribbean capable of supporting a strike or invasion of Cuba, and administration officials now assess the island's government could collapse as soon as this summer, according to Politico and Axios. The buildup awaits a presidential order, and no such directive has been confirmed as of late May 2026. [POLITICO]^[1]

The naval component of the buildup is substantial. The USS Nimitz carrier strike group entered the Caribbean on May 20, accompanied by several destroyers and guided-missile cruisers. ^[2][3] The Iwo Jima Amphibious Ready Group and its embarked 22nd Marine Expeditionary Unit remain in the region, along with the guided-missile cruiser USS Lake Erie and the littoral combat ship USS Billings. ^[4] Accompanying assets, as reported by Politico, include amphibious ships carrying approximately 2,500 Marines and several guided-missile destroyers and cruisers capable of launching precision strikes onshore. ^[1] The Navy's built-up presence in the region is described as the largest in the world outside the Middle East, and would allow the United States to act immediately. ^[1] Advanced drones and surveillance aircraft have circled Cuba for months, while fighter aircraft are available from bases in Florida and Puerto Rico. ^[1]

The current posture mirrors, in part, the sequence that preceded the January 2026 capture of former Venezuelan President Nicolas Maduro. The USS Iwo Jima and USS San Antonio were repositioned to waters north of Cuba within days of the operation that resulted in Maduro's capture by Delta Force personnel; Maduro was transferred by helicopter to the Iwo Jima and subsequently taken to New York, where he faces federal drug trafficking charges. ^[5] The Justice Department's unsealing of an indictment against former Cuban President Raul Castro on May 21, the timing of the Nimitz strike group's arrival, more than 240 sanctions imposed since January, the interception of at least seven oil tankers bound for Cuba, and CIA Director John Ratcliffe's May visit to Havana to warn that the window for talks is closing are, in sequence, consistent with the pressure campaign Washington ran against Caracas. ^[6]

The Justice Department charged Raul Castro and other Cuban officials with murder for their roles in the Feb. 24, 1996, shoot-down of two unarmed Brothers to the Rescue civilian aircraft over international waters; U.S. Southern Command confirmed the Nimitz carrier strike group is operating in the Caribbean in the wake of that announcement. ^[7] The charges against Castro invoke federal murder statutes and mark the first time a former Cuban head of state has been criminally indicted in a U.S. court. The indictment, combined with overt naval positioning, tracks the rhetorical and legal scaffolding the administration erected before military operations against Venezuela: terrorism designations, criminal charges against the targeted government's leadership, and visible force concentration in the region.

Secretary of State Marco Rubio framed the stakes in direct terms at a May 27 Cabinet meeting. Rubio told reporters that Cuba "has been one of the leading sponsors of terrorism in the entire region," and warned that "having a failed state 90 miles from our shores run by friends of our adversaries poses a threat to the national security of the United States." ^[6] Those remarks came the same day the Nimitz strike group's Caribbean deployment was publicly confirmed by U.S. Southern Command. ^[6][7] Trump told reporters that previous presidents have looked to intervene in Cuba for "50, 60 years" and "it looks like I'll be the one that does it." ^[8]

The administration has not cited a specific statutory authorization for any potential military action against Cuba. The Venezuela operation was conducted under the president's Article II commander-in-chief authority and framed as a law enforcement action, a legal posture that drew congressional scrutiny. The administration informed Congress that Venezuelans killed in earlier boat strikes were "enemy combatants" and invoked commander-in-chief powers in a manner analogous to the post-9/11 War on Terror, though Congress never authorized military force against Venezuela, as it had against al-Qaeda and related groups. ^[9] Any Cuba operation would face the same threshold question. In March congressional testimony, Gen. Francis Donovan, the head of U.S. Southern Command, denied that the United States was actively rehearsing or planning for a takeover of Cuba. ^[10] U.S. Southern Command declined to engage directly with questions about Cuba planning: "We do not comment on specific operational planning or contingency plans nor speculate on hypothetical scenarios," a spokesperson told Military.com. ^[10]

Cuba continues to face acute fuel shortages stemming from the loss of Venezuelan oil supplies and deterrence of foreign investment. ^[2] Havana has responded to the escalating pressure by ordering its armed forces to prepare for potential conflict and conducting nationwide defensive exercises. ^[2] Mark Cancian, a senior analyst at the Center for Strategic and International Studies, told Politico the carrier strike group's arrival "is likely there primarily for intimidation, though it could be used in a military operation if needed." ^[11] The administration faces a practical constraint: many of the Navy's largest warships are approaching 10 months continuously at sea, and Pentagon officials are wary of overextending naval crews while much of the broader force remains committed to operations against Iran. ^[11]

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