The Trump administration has ratcheted up its pressure campaign on Cuba, the island only 90 miles from the southern tip of Florida, as talks with Iran have still not resulted in a breakthrough.
President Donald Trump has tried to squeeze the communist government for months, dating back to the military’s capture of former Venezuelan dictator Nicolas Maduro, which cut off Cuba’s oil lifeline. The administration twisted the island country’s arm further this week with the unveiling of a criminal indictment of former Cuban President Raul Castro and five others of crimes connected to the Feb. 24, 1996, attack on two aircraft operated by the Miami-based Cuban exile group Brothers to the Rescue.
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The Castro indictment paves the way for the United States to carry out a similar raid on him, as the president authorized for Maduro. The Venezuelan dictator had been indicted on narco-trafficking charges in 2020.
“It’s a daunting and complex and highly controversial proposition to remove another country’s government, especially when that country is posing no discernible or notable threat to the USA,” Michael O’Hanlon, the director of research in the Foreign Policy program at the Brookings Institution, told the Washington Examiner. “In other words, I’m not going to make a prediction on what Mr. Trump might do, but I do sense a lot of churn and the possibility of a major decision and action.”

Secretary of State Marco Rubio, whose Cuban parents immigrated to the U.S., said on Thursday, “Cuba not only has weapons that they’ve acquired from Russia and China over the years, but they also host Russian and Chinese intelligence presence in their country not far from where we’re standing right now.”
O’Hanlon argued that Rubio’s remarks sound “entirely like a pretext,” adding, “Cuba would never be so stupid; it would be an open invitation to the very attack they should want to avoid—and that [President John F. Kennedy] promised not to conduct in the resolution of the 1962 Cuban Missile Crisis.”
Trump said Thursday that presidents have considered military action against Cuba for decades, but “it looks like I’ll be the one that does it. So, I would be happy to do it.”
The U.S military announced on Wednesday that the USS Nimitz and three escort warships entered the southern Caribbean Sea shortly after the indictment was announced. Trump denied that the arrival of the warship was meant to intimidate Cuba.

The Pentagon deployed the world’s largest aircraft carrier, the USS Gerald R. Ford, to the Caribbean Sea during the military buildup in the region last year before the Maduro raid. By December 2025, it had become the largest U.S. deployment to the Caribbean since the 1989 invasion of Panama.
In the weeks that followed the Maduro operation, Trump renewed threats against Colombia, criticized Mexican leadership, predicted Cuba’s government would collapse, reiterated his desire to take over Greenland, and told Iranian protesters to keep their movement going because “help is on the way.”
“It does seem as though the administration was influenced at least in part by the relative success of the Venezuela operation, and I think the biggest risk that we’ve now seen is exactly this idea of miscalculation of overreach,” Mona Yacoubian, a Middle East expert with the Center for Strategic and International Studies, told the Washington Examiner. “That might be a challenge should we move forward and seek to undertake operations in Cuba, and also the mistake of applying a simplistic approach where what worked in one context can simply be copied and pasted into an entirely different context.”
Simultaneously, there has been no resolution to the war in Iran. The Iranian military and the Revolutionary Guard Corps have still not agreed to allow commercial vessels to transit the Strait of Hormuz, which continues to hurt the global economy, while the U.S. Navy is continuing its counter-blockade of Iranian ports.

Yacoubin added, “I think the stalemate is really defined by the fact that both sides think they have the upper hand and can coerce the other to their way, and so I think that’s what’s feeding this stalemate, but unfortunately it is an unstable stalemate or equilibrium.”
The president warned this week that he called off a near-imminent attack on Iran at the request of Persian Gulf leaders, who have come under Iranian missile and drone attacks. If the U.S. military were to restart offensive military operations inside Iran, the Islamic regime would likely respond by going after countries in the Persian Gulf, such as the United Arab Emirates, Qatar, and Saudi Arabia.
Trump said on Wednesday he’s “in no hurry” to make a deal, even though the continued closure of the strait and the increased cost of gas could hurt the Republican Party in November’s midterm elections.
Iran’s ability to maintain the closure is part of its asymmetric warfare. Despite being badly degraded during the conflict, the geography of the strait benefits it.
“The president’s policy has just been completely unrestrained, whether it’s in the Western Hemisphere or in the Middle East, and it’s been characterized by an inability to understand the limits of US military power and what it can accomplish, and also even the benefits of what it would would mean for the United States if these leaders were removed,” Rosemary Kelanic, an expert with Defense Priorities, told the Washington Examiner.
Adm. Brad Cooper, the commander of U.S. Central Command, said in a congressional hearing last week that U.S. and Israeli forces have “significantly degraded” Iran’s military capabilities and “they no longer threaten regional partners or the United States in ways that they were able to do before.”
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He added, “The Iranian capability to stop commerce has been dramatically depleted through the strait, but their voice is very loud, and those threats are clearly heard by the merchant industry and insurance industry.”
It’s also unclear if the U.S. and Iran have made any progress on reconciling their opposed viewpoints on Iran’s nuclear and ballistic missile programs, what to do about Iran’s support for proxy forces throughout the region, or what will happen with the more than 900 pounds of highly enriched uranium that is believed to be deeply buried under ground in one of the three facilities the U.S. military bombed last year.
