U.S. policy toward Cuba in 2026 centers on a maximum-pressure campaign of economic sanctions, an oil blockade, and legal measures such as the May indictment of Raúl Castro, following the January executive order targeting foreign oil suppliers after the Maduro operation in Venezuela. Diplomatic talks have produced prisoner releases and meetings including a CIA director visit, while President Trump has repeatedly urged a “deal” or “friendly takeover” rather than direct military action. Pentagon asset positioning in the Caribbean and regime-change rhetoric have raised invasion concerns, yet no offensive operations have begun by mid-year. Traders assign the “No” outcome 76.5 percent probability because the administration has prioritized coercive diplomacy and sanctions over the high costs and risks of a full-scale invasion within the calendar year.