John Bolton, former National Security Advisor under Donald Trump, cautioned on Wednesday that the current U.S. administration might be on the verge of repeating its Venezuelan missteps with Cuba by accepting superficial gestures from the regime without demanding genuine structural change.
Bolton remarked on his profile on X, "Trump appears unable to see that there hasn’t been a true regime change in Venezuela. He risks making the same mistake with Cuba if he continues his approach with Maduro. Havana will be more than willing to placate Trump temporarily to secure any assistance or support it can get from Washington."
U.S. officials have verified that high-level negotiations with Cuba are ongoing, albeit insiders suggest the talks are still in a very early and informal stage.
Comparisons with Venezuela
Bolton draws a direct comparison with the Venezuelan situation. The January 3, 2026, apprehension of Nicolás Maduro was touted as a success of Trump’s foreign policy. However, Bolton argues that the Venezuelan outcome was likely pre-arranged with the Trump administration since the autumn, without leading to a real shift in the power structure.
Economic Engagement Concerns
Previously, Bolton criticized the idea of economic engagement with the island, pointing out the absence of a private sector capable of purchasing oil in Cuba, which would render any trade scheme that doesn’t directly benefit the Cuban state unfeasible.
Trump had stated, "Very soon, we will either reach an agreement or do whatever is necessary regarding Cuba," while from Havana, Miguel Díaz-Canel responded with warnings of a “people’s war” in the face of any potential aggression.
Understanding U.S. Relations with Cuba
What is John Bolton's main criticism of Trump's approach to Cuba?
Bolton criticizes Trump's approach for potentially repeating past mistakes made with Venezuela, namely accepting superficial gestures without securing actual structural changes.
How does Bolton compare the situation in Cuba to that in Venezuela?
Bolton draws a parallel between the two by suggesting that, similar to Venezuela, any perceived successes might be superficial and pre-arranged, without leading to real regime change.
What are the potential challenges of economic engagement with Cuba, according to Bolton?
Bolton argues that because Cuba lacks a private sector to participate in oil purchases, any trade agreements would likely only benefit the state, not the broader Cuban economy.