Cuba's tightrope: oil, prisoners, and a deal with washington?
Havana is teetering. A sanctioned Russian oil tanker, the Anatoly Kolodkin, recently unloaded its cargo, while a simultaneous prisoner release has sparked a flurry of speculation: is cuba negotiating a radical shift with the United States?
The paradox of trump's policy
Just weeks ago, Donald Trump declared a complete oil and money embargo on Cuba. Yet, he now shrugs off the arrival of the Anatoly Kolodkin, seemingly waving it through. The timing is peculiar, to say the least. The island’s economy is collapsing, crippled by a US blockade that has choked off vital trade and tourism. Airlines from major nations—Canada, Russia, China, France—have ceased operations, and Iberia is following suit by the end of May. Petrol stations stand shuttered, and blackouts are a daily occurrence.
One man, speaking outside a church in El Cobre, a site of profound religious significance, captured the desperation: “Everything is collapsing – health, education, transport, everything.” The island’s population, reduced by a staggering 2 million in the last five years due to emigration, is exhausted. Information trickles in, invariably sourced from US leaks, hinting at ongoing, and seemingly irreconcilable, negotiations. Trump has vowed to “take” the island, while Cuba insists its political system is off the table.
A humanitarian gesture, or something more?
The release of 2,010 prisoners, initially framed as a gesture for Holy Week, has fueled the suspicion that something larger is at play. Diplomats are struggling to interpret these events, with one ambassador suggesting a cynical, but plausible, explanation: “One option is that it’s a tactical move by the White House, so that as the humanitarian emergency worsens, they can point to something specific they did.” However, Trump's infrequent displays of humanitarian concern make this explanation less convincing.
William LeoGrande, a professor at American University, believes the prisoner release points to a more optimistic scenario: “It suggests that the two sides may be making reciprocal gestures of good will to advance the conversations they have been having.” The arrival of another tanker, the Sea Horse, further complicates the picture, moving from the Atlantic to Venezuela, a nation eager to appease Trump's demands following the US's actions against Nicolás Maduro.
The rise of the mipymes and castro's kin
But there’s another, crucial layer to this story. Since 2021, Cuba has seen the rise of over 10,000 small and medium-sized private businesses—Mipymes—transforming the economic landscape. These businesses, visible in corner stores and bustling container trucks, have created a new class of wealthy Cubans, many with ties to the regime and Gaesa, the army’s powerful economic wing. Raúl Guillermo Rodríguez Castro, grandson of former president Raúl Castro and son of the late head of Gaesa, Luis Rodríguez López-Calleja, is reportedly involved in these negotiations.
Even more striking is the emergence of Sandro Castro, Fidel's grandson and a popular influencer. While often criticized for his lavish lifestyle, diplomats reveal he is also a successful businessman and importer. His recent criticisms of President Díaz-Canel, which would normally trigger state security intervention, have been conspicuously ignored, suggesting a shift in the political winds. Díaz-Canel’s potential removal from power has been floated by Washington as a condition for further talks.
A transactional future?
The emerging scenario appears to be a transactional one: Cuba would open its economy to the US, while senior regime members, including several Castros, retain power and influence. This would mirror events in Venezuela and provide Trump with a political victory. As one senior diplomat in Havana put it, “If the Americans are saying, ‘you can keep your businesses, but you need to open the economy up to the US too,’ then I can see that happening.”
But what of the roughly 40% of Cubans who remain outside the private sector or reliant on remittances? These are often the elderly, the bedrock of the revolution that promised them lifelong security. They face a grim future, staring down the barrel of starvation as a new elite thrives on connections to Washington. The promise of a “friendly” takeover rings hollow for those left behind.