CIA Director Flies to Havana, Grand Jury Expected by May 20 as Castro Indictment Moves from Rumor to Reality

What's New Since Our Last Report

When we first covered this story, the indictment was described as imminent. Now we have specifics.

According to NBC News, charges against 94-year-old Raúl Castro are expected to be revealed at a public event in Miami on May 20 — Cuban Independence Day. The choice of date carries symbolic weight.

The case must still clear a grand jury. According to NBC News, two U.S. officials familiar with the matter confirmed the Justice Department is actively pushing it forward.

Ratcliffe Goes to Havana

CIA Director John Ratcliffe flew directly to Havana on Thursday and met with Raúl Guillermo Rodríguez Castro — known as "Raulito" — Raúl Castro's grandson and the primary back-channel between the Cuban government and Washington.

According to CBS News, a CIA official stated Ratcliffe personally delivered Trump's message that the U.S. is "prepared to seriously engage on economic and security issues, but only if Cuba makes fundamental changes." The official added Cuba can "no longer be a safe haven for adversaries in the Western Hemisphere."

Ratcliffe's Havana trip happened the night after protests spread across the Cuban capital amid 22-hour blackouts, according to The Guardian.

Cuba Has Run Out of Fuel

Cuba is not just struggling with an energy crisis — it has collapsed.

Vicente de la O Levy, Cuba's energy minister, told state television this week: "We have absolutely nothing." No fuel oil. None.

The Trump administration's oil blockade — which includes threatening heavy tariffs on any country that exports oil to Cuba, according to CBS News — has effectively shut off the island's energy supply. Cuba's energy grid was already on life support. The NYT published a photo essay on Cuba plunging into darkness as the U.S. cuts off oil supply.

The Venezuela Blueprint, Executed

Multiple sources — NBC News, The Guardian, NYT — draw the explicit comparison to Venezuela. In January, Trump ordered a military operation that captured Venezuelan President Nicolás Maduro and flew him to New York on drug trafficking charges. Maduro has pleaded not guilty.

The Cuba strategy mirrors it: indict the leader, use the indictment as legal justification for escalating pressure, and wait for the regime to crack.

Secretary of State Marco Rubio, flying to China this week, put it plainly according to The Guardian: "I don't think we're going to be able to change the trajectory of Cuba as long as these people are in charge."

Trump, asked about the indictment on Air Force One Friday, said: "I'll let DOJ comment on it." Then added: "They are really a nation, a country in decline."

The Legal and Strategic Logic

The 1996 Brothers to the Rescue shootdown wasn't a gray area. According to CBS News, the Organization of American States found the planes were shot down outside Cuban airspace, that Cuba fired without warning, and that it violated international law. Four Cuban Americans died.

Meanwhile, some commentary treats the indictment as a guaranteed outcome. Pedro Freyre, a leading Cuban American lawyer in Miami, told The Guardian: "You can get a grand jury to indict a ham sandwich." The harder question is what happens after. Raúl Castro is 94, living in Cuba, and not getting on a plane to New York voluntarily.

The Indictment as Political Tool

An indictment of a 94-year-old man who will never see the inside of an American courtroom serves as a political weapon alongside law enforcement. The indictment hands the Trump administration a formal legal framework to escalate sanctions, justify further economic warfare, and rally Cuban exile communities in Miami ahead of the 2026 midterms.

Whether it forces Cuba's communist leadership to make concessions is unclear. The regime has survived 60-plus years of American pressure. The difference this time: Venezuela, Cuba's primary economic lifeline, is now under U.S. control. And Cuba has zero fuel.

What It Means for Regular People

For Cuban Americans: this is the most aggressive U.S. action against the Castro regime in decades.

For taxpayers: this pressure campaign has real costs — military surveillance flights, CIA director travel, expanded sanctions enforcement — and no clear exit strategy if the Cuban regime refuses to fold.

For Cubans on the island: blackouts, empty gas stations, and a government uninterested in protecting them from the consequences of its own policies.

The indictment announcement comes May 20.