The Trump administration’s post-Venezuela strategy has centered on an energy blockade and sanctions targeting Cuba’s oil imports since January 2026, triggering acute fuel shortages, blackouts, and economic strain that Cuban leaders describe as an existential crisis. Executive orders, tariffs on third-country suppliers, and the Justice Department’s indictment of Raúl Castro over the 1996 plane shootdown have intensified legal and diplomatic pressure, while naval assets including the USS Nimitz carrier group, Marine units, and expanded surveillance flights signal military options under review. Cuban ties to Russia, Iran, and China—evidenced by drone acquisitions and reported intelligence facilities—feature in U.S. national-security assessments, alongside mixed signals of backchannel talks and aid offers conditioned on reforms. Traders weigh these developments against the absence of strikes to date, upcoming midterm elections, and Cuba’s entrenched regime as key variables shaping probabilities for limited action versus continued coercion.