Trump's cuba gambit: oil, pardons, and a shifting power dynamic

Havana's economic collapse has reached a critical juncture, but a curious week of events – a Russian oil tanker docking amidst a US embargo, a sudden prisoner release, and whispers of backchannel negotiations – suggests a far more complex picture than simple defiance. Is the Trump administration subtly reshaping Cuba’s future, and at what cost?

The anatomy of a calculated risk

The arrival of the Anatoly Kolodkin, laden with 700,000 barrels of Russian crude, initially seemed a blatant disregard for President Trump's earlier pronouncements of a “zero” oil flow to Cuba. Yet, just days later, the president’s seemingly casual allowance of the shipment, coupled with the release of over 2,000 prisoners – ostensibly a humanitarian gesture for Holy Week – sparked speculation about a quiet diplomatic dance.

The US oil blockade has delivered a brutal blow to Cuba. Tourism, once a lifeline, has evaporated as airlines from major nations ceased operations, and Iberia is poised to follow suit at month’s end. Petrol stations stand shuttered, and daily blackouts have become the norm for the island’s dwindling population—estimated at just 9.5 million after a mass exodus. The desperation is palpable; one resident outside a church in El Cobre lamented, “Everything is collapsing – health, education, transport, everything.”

A transactional approach: new businesses and castro's kin

While a complete overhaul of the Cuban regime remains improbable, a subtle shift is underway. Since 2021, Cuba has seen a surge in small to medium-sized private businesses, known as Mipymes, flourishing across the island. These ventures, while offering a glimmer of hope for economic diversification, are also concentrated within a select group – a cohort of increasingly wealthy Cubans with close ties to the regime and Gaesa, the army's powerful economic wing. Raúl Guillermo Rodríguez Castro, grandson of the former president and son of Gaesa’s former head, sits squarely within this circle, hinting at a potential power structure emerging from the economic reforms.

Adding further intrigue, Fidel Castro’s grandson, Sandro Castro, a prominent social media influencer, recently voiced his opinion to CNN that the current president, Miguel Díaz-Canel, “is not doing a good job.” Such a statement would have traditionally triggered state security intervention, but the unusual silence suggests a loosening of control, perhaps as a negotiating tactic.

The human cost of political maneuvering

But what of the roughly 40% of Cubans who remain untouched by the burgeoning private sector or remittances from abroad? These are often the elderly, those who dedicated their lives to the revolution's promise of cradle-to-grave security. For them, the potential for economic liberalization – orchestrated from the top down – offers little solace, and their future remains bleak. The whispers of a “friendly takeover,” mirroring events in Venezuela, could leave them stranded on the periphery of a new, transactional Cuba.

The US appears to be pursuing a strategy where senior regime members, including members of the Castro family, retain influence while the economy opens to American investment. The question now is whether this calculated gamble will ultimately benefit the Cuban people or simply consolidate power within a select few, leaving the vast majority to face an uncertain and increasingly precarious future.