As news breaks of CIA Director John Ratcliffe’s visit Havana On May 14, Trump ally and political activist Laura Loomer posted a blunt message on X the next day: “Cuba is about to be liberated.” This article captures exactly where Washington’s actions are pointing.

Ratcliff flies directly to Cuba to deliver President’s stern warning Donald Trump On the same day, news broke that the United States was prosecuting the island’s leaders and taking coordinated action. cuba President Raul Castro is attacking the communist government from multiple directions at once.
CIA director arrives in Havana with Trump’s ultimatum
Ratcliffe’s visit makes him the highest-ranking official ever in the Trump administration cuba. According to a statement from the CIA, he traveled to Havana Personally telling Cuban leaders that “the United States is ready to engage seriously in economic and security issues, but only if Cuba makes fundamental changes,” new york times.
He met with Raul G Rodriguez Castro, known as “Raulito” or “El Cangrejo,” the powerful grandson of former President Raul Castro and Cuba’s interior minister and intelligence chief. His most immediate demand is that Cuba close intelligence listening posts run by Russia and China on the island.
U.S. Secretary of State Marco Rubio made the administration’s position clearer in an interview with Fox News, saying he doubted it would be possible to change Cuba’s trajectory “as long as these people are in charge.”
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Raul Castro faces prosecution in 1996 plane shooting down
Hours after the C.I.A. visit, two sources told USA Today The United States is proceeding with a 30-year-old case against former Cuban President Raul Castro, 94. On February 24, 1996, Cuban Air Force MiG fighter jets shot down two unarmed civilian aircraft operated by the humanitarian organization Brothers to the Rescue in the Florida Straits, killing three Americans and one U.S. permanent resident. The U.S. Congress later concluded that the planes “were flying unarmed, defenseless aircraft on the same mission as hundreds of aircraft flown since 1991 and posed no threat to the Cuban government,” USA Today reported.
In February 2026, four Republican congressmen formally urged Trump to file charges, saying Castro was “responsible for the cold-blooded murder of three Americans and one permanent resident of the United States.” “Based on publicly available information, we understand that on February 24, 1996, Raul Castro ordered a Cuban MiG fighter jet to engage and destroy two Rescue Brothers civilian aircraft over international waters,” their letter reads.
The prosecution, led by Jason A. Reding Quinones, the U.S. Attorney for the Southern District of Florida, may include drug trafficking charges in addition to the 1996 shootdown charges, the New York Times reported.
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U.S. pressure intensifies, Cuba succumbs
Ratcliffe’s visit came just a day after Cuban Energy Minister Vicente de la O Levy made a shocking admission: “We have absolutely no fuel, absolutely no diesel. In Havana, the power outage lasted more than 20 or 22 hours today.”
The island’s energy crisis has been worsening for more than two years. Venezuelan oil, Cuba’s long-time lifeline, stopped flowing completely in January after the Trump administration seized on Venezuela’s leader. A U.S.-imposed blockade subsequently cut off all remaining foreign oil shipments. Cubans can only cook with charcoal or wood, and some take to the streets banging pots and pans in frustration.
According to the New York Times, the Cuban government firmly refuted and stated through its official newspaper Granma: “Once again, it is clear that the island does not harbor, support, finance or allow terrorist or extremist organizations; it does not have any foreign military or intelligence bases on its territory, has never supported any hostile activities against the United States, and will not allow Cuba to take any actions against other countries.”
However, Cuba’s current president, Miguel DÃaz-Canel, did not comment directly on Ratcliffe’s visit, but publicly accepted the offer of humanitarian aid in a social media post. A day earlier, he acknowledged that the energy situation was “especially tense” and blamed Washington directly. “There is only one reason for this dramatic deterioration: the United States’ genocidal energy blockade of our country,” he said. write on X.

