CIA Director John Ratcliffe made a surprise visit to Havana this week in what is believed to be only the second time a sitting CIA chief has set foot in Cuba since the island became a communist state in 1959. Ratcliffe met with senior Cuban officials, including Interior Minister Lázaro Álvarez Casas and Raúl Guillermo Rodríguez Castro — a grandson of former revolutionary leader Raúl Castro — to deliver a message from President Donald Trump: the United States is prepared to engage seriously on economic and security matters, but only if Cuba undertakes what Washington calls "fundamental changes." No specific conditions were publicly detailed.

The Cuban government confirmed the talks took place at Washington's request and said its representatives used the meeting to demonstrate that Cuba poses no threat to US national security. Havana has long disputed its designation on Washington's state sponsors of terrorism list, which was reinstated by Trump in January 2025 as one of his first actions after returning to office. Cuban officials argued there is no legitimate basis for the sanctions, stating the country neither finances nor harbours terrorist organisations. President Miguel Díaz-Canel, writing on X after the visit, made Havana's priorities plain: what Cuba needs most, he said, is for the oil blockade to be lifted — not aid packages tied to political conditions, one of which Cuba had already rejected.

The backdrop to the talks is a severe humanitarian crisis. US pressure on countries to halt oil sales to Cuba — backed by the threat of tariffs announced by Trump in January — has left the island generating barely 40 percent of the fuel it needs to keep its economy running. A Russian oil tanker managed to deliver a shipment despite the restrictions, and Moscow has pledged a second, though reports indicate that vessel has been stalled in the Atlantic for weeks. The resulting fuel shortages have crippled Cuba's already-ageing power grid: this week, a major grid collapse cut electricity to all eastern provinces stretching from Guantánamo to Ciego de Ávila, while Havana residents endured rolling blackouts lasting up to 24 hours.

The energy misery has fuelled rare public unrest. Hundreds of Cubans took to the streets in Havana on Wednesday evening, banging pots and pans, blocking roads with burning rubbish, and chanting anti-government slogans. While many demonstrators directed their anger at the communist authorities, the government continues to attribute the crisis squarely to Washington's sanctions.

Complicating the diplomatic picture further, US media reported on Friday that American prosecutors may be preparing to indict 94-year-old former president Raúl Castro — grandfather of the very official who met with Ratcliffe — over his alleged role in ordering the 1996 shoot-down of planes operated by a Cuban exile organisation, which killed four people. Florida Governor Ron DeSantis publicly welcomed the prospect. Whether the simultaneous pursuit of high-level talks and a potential prosecution of Cuba's most revered revolutionary figure reflects a coherent strategy or internal contradictions within the Trump administration remains to be seen, but it underscores just how fraught the path to any normalisation will be.