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CIA chief Ratcliffe in Havana as Raul Castro indictment looms; Loomer posts 'Cuba is about to be liberated'

The article outlines a sequence of events starting with Cuba's energy crisis deepening in January, followed by a high-profile CIA visit to Havana on May 14, 2026, and subsequent moves including potential indictments against Raul Castro and public responses from Cuban and US officials, with a notable social media post from Laura Loomer.

Why It Matters

The events signal heightened U.S. pressure on Cuba across diplomatic, legal, and security fronts amid Cuba's ongoing energy crisis and regional tensions.

Timeline

18 Events

Indictment seen as to be unsealed on May 20; victims' event planned

May 15, 2026

The indictment against Raul Castro is expected to be unsealed in Miami on May 20, and a separate event to honor victims is planned for that day.

Jason Reding Quiñones oversees related investigations

May 15, 2026

The top federal prosecutor in Miami, Jason Reding Quiñones, is a Trump ally who is overseeing an investigation of John Brennan and a wider set of inquiries into Trump-related investigations.

Miami prosecutors to host victims' event on May 20

May 15, 2026

The prosecutors' office in Miami will host an event on May 20 to honor victims of the 1996 incident.

DOJ official says indictment to be unsealed on May 20

May 15, 2026

A US Justice Department official said federal prosecutors expect to unseal an indictment against Castro on May 20, based on the 1996 incident.

Miami Herald reports planned indictment against Raul Castro

May 15, 2026

The planned announcement of criminal charges against Raul Castro was first reported by the Miami Herald.

May 14, 2026: Ratcliffe visits Havana; message to Cuba

May 14, 2026

CIA chief John Ratcliffe delivered a message from Trump during a rare visit to Havana on Thursday that the US would engage with the government on economic and security issues only if it makes fundamental changes.

Raul Castro hands over leadership of the Cuban Communist Party

2021

Raul Castro handed over leadership of Cuba's Communist Party in 2021.

Raul Castro steps down as Cuba's president

2018

Raul Castro stepped down as Cuba's president in 2018.

1996: Cuban jets shoot down exile planes

1996

During 1996, Cuban jets shot down planes operated by a group of Cuban exiles; Raul Castro was defense minister at the time, and the incident is cited as the basis for potential charges.

May 15, 2026: Diaz-Canel accepts humanitarian aid via social media

May 15, 2026

President Diaz-Canel publicly accepts an offer of humanitarian aid in a social media post, following earlier comments blaming the blockade for Cuba’s energy hardships.

May 15, 2026: Rubio Fox News interview on Cuba policy

May 15, 2026

Secretary of State Marco Rubio discusses the administration's stance on Cuba in a Fox News interview, asserting it may be difficult to change Cuba's trajectory while current leaders remain in charge.

May 15, 2026: Laura Loomer posts on X about Cuba's liberation

May 15, 2026

Trump ally Laura Loomer posts on X declaring that Cuba is about to be liberated, reflecting ongoing U.S. political messaging surrounding Cuba.

May 14, 2026: Diaz-Canel acknowledges energy tensions on X

May 14, 2026

President Miguel Diaz-Canel writes on X acknowledging the energy situation is particularly tense and blaming the United States for the blockade driving the energy crisis.

May 14, 2026: Granma statement denying foreign bases or support for extremism

May 14, 2026

Cuba's Granma publishes a response asserting that the island does not harbor or support terrorist or extremist organizations, has no foreign military bases, and has not supported hostile actions against the United States.

May 14, 2026: Indictment move against Raul Castro reported

May 14, 2026

Hours after Ratcliffe's visit, USA Today reports that the United States is moving to indict Raul Castro over the 1996 Brothers to the Rescue shootdown, with potential drug trafficking charges discussed by sources.

May 14, 2026: CIA Director Ratcliffe visits Havana

May 14, 2026

CIA Director John Ratcliffe travels to Havana to convey a warning from President Trump. He meets Raul G Rodriguez Castro and Cuba’s interior minister and head of intelligence, delivering a demand that Cuba make fundamental changes and shut down listening posts run by Russia and China; the visit is described as a high-level exposure of U.S. stance.

May 13, 2026: Cuban energy minister admission of fuel shortages

May 13, 2026

Cuban Energy Minister Vicente de la O Levy publicly states there is no fuel oil or diesel available and notes blackouts exceed 20 hours in Havana.

January 2026: Venezuelan oil stops flowing to Cuba

January 2026

Cuba's energy supplies are disrupted as Venezuelan oil stops flowing entirely in January after the Trump administration seized Venezuela's leader, contributing to a worsening energy crisis.