CommentRather than invading Cuba, has Donald Trump had a better idea? The US president can rarely be accused of playing the long game, but calling for the arrest of 94-year-old former leader Raul Castro could be a sign he is learning from his foreign policy blunders – and that he wants a regime change he can be proud of, says Mary Dejevsky.
Thursday 21 May 2026 16:05 BST
Trump on Castro indictment: US freeing up Cuba and there won't be an escalation.
What with his delayed visit to Beijing, his unresolved war with Iran, and some largely below-the-radar talks about new military bases in Greenland, you might have thought that President Donald Trump has enough to do. But no. Just as he was embarking on talks with China’s Xi Jinping, a US-liveried plane carrying the director of the CIA, John Ratcliffe, was landing in Havana.
Cuba has been high on the President’s foreign policy agenda since early in his second term, and talks have been going on quietly between the two countries since at least the start of this year. The successful US military operation to extract Nicolas Maduro from his presidential palace in Caracas to a prison in Brooklyn fuelled speculation that Cuba could be Trump’s next candidate for Western hemisphere regime change. In practical terms, the removal of Maduro removed one of Cuba’s last remaining sources of support, precipitating acute shortages of energy and food, and a rash of street protests. And while power cuts, rationing and breakdowns in transport have been regular features of life in Cuba for years, the enforced change of government in Venezuela suggested that the days of Havana’s beleaguered regime really might be numbered.
On the face of it, it seems hard to square the summary action of the US against Venezuela and the reckless risk-taking of the US-Israel attacks on Iran with what, by comparison, seems – so far – the kid-glove treatment of Cuba. Why, it might be asked, the difference, and what, for the US, might be the desired outcome, if there is one?
Perhaps it is simply that the US, via its intelligence channels and the Cuban diaspora in the US, has a more realistic idea of how negligible a threat today’s debilitated Cuba poses to anyone. The history of attempted US interventions would also suggest that at least some armed resistance might follow any military intervention, with the risk of a potentially messy outcome that Trump might prefer to avoid, especially in the run-up to the mid-term Congressional elections.
On the other hand, the US now appears to be setting a very specific price for the US$100m in aid that the CIA head said is on offer. Along with “fundamental changes” (not defined) in policy, that price would now seem to include the extradition of Raúl Castro, a former president of Cuba and brother of Fidel, in connection with the 1996 shooting down of two small planes carrying exiles, in which three of the four people killed were US citizens. A grand jury indictment from a US court is said to be close to completion.
How far handing over Castro might be negotiable or even feasible remains to be seen. The former president is now 94, and while the Castro clan still wields influence (Raúl’s grandson, another Raúl, was in the Cuban team meeting Ratcliffe), the rallying power of the name may be less than it once was. An exception might be for Cuban exiles in the US, to whom this particular measure may be primarily addressed as a possible quid pro quo for the normalisation of US-Cuba relations that they have long opposed.
Another condition for US aid is that it should be administered by churches, charities and non-government organisations, effectively bypassing the regime. This would allow the immediate humanitarian emergency to be mitigated, while making it hard for the regime to claim the credit and perhaps loosening its hold on power.
Trump can rarely be accused of trying to play the long game, but could this be his calculation here? President Diaz-Canel responded to the CIA-communicated offer of aid, saying not unreasonably that it might be more effective for the US simply to lift its blockade. Seen from Washington, however, it would be equally reasonable to ask: why would it?
The situation across Cuba is now so dire, that it must surely be only a matter of time before officials decide that at least engaging with Trump’s conditions is the best option on offer. That is, unless the US president loses patience and gives the green light to armed exiles to chance their hand first.
