Trump Administration Escalates Pressure on Cuba Using Venezuela-Style Strategy

The Trump administration is escalating pressure on Cuba with a strategy that appears to borrow from its approach to Venezuela, according to Bloomberg’s “Big Take” podcast and related reporting. The campaign includes new sanctions and military moves in the region, all aimed at weakening Havana’s government at a moment when Cuba’s economy is already under severe strain.

Bloomberg reports that this month the administration indicted former President Raúl Castro, announced the deployment of additional military assets to the region and released a video message featuring Secretary of State Marco Rubio blaming Cuba’s economic troubles on its own government. The podcast says those steps come less than five months after the U.S. captured one of Havana’s strongest allies, Venezuela’s Nicolás Maduro, which helped choke off oil supplies to Cuba and contributed to widespread power outages on the island.

The administration’s logic, as described in Bloomberg’s discussion with State Department reporter Eric Martin, is that pressure on Venezuela can be a blueprint for Cuba. The idea is to squeeze the Cuban government economically and politically until it is forced into concessions or negotiations. But Bloomberg notes that the Cuba case is not identical to Venezuela’s, and that the strategy may not play out in the same way in Havana.

That distinction matters because Cuba is already in deep distress. Other reporting cited in the cluster says the island is facing fuel shortages, blackouts, food and water scarcities, and a broader economic breakdown that has pushed daily life close to a standstill. One analyst quoted in a related discussion said Cuba is in its worst crisis in decades, with millions having left in recent years and the opposition too fractured to offer an immediate political alternative.

The pressure campaign also carries major humanitarian risks. As reported by the Council on Foreign Relations in a separate podcast discussion, cutting off key imports and oil supplies has immediate effects on transportation, electricity and basic services, leaving ordinary Cubans in the middle of a confrontation between Washington and Havana. The same discussion framed the situation as a kind of “game of chicken,” with both governments waiting to see who blinks first.

What happens next will likely depend on whether the Trump administration is prepared to keep tightening the squeeze or shift toward some kind of bargain. Bloomberg’s podcast suggests the White House is testing whether the Venezuela playbook can be adapted to Cuba, but the island’s severe economic weakness, the government’s resilience and the humanitarian costs of further pressure make the outcome uncertain.