US pressure on Cuba has intensified under the Trump administration through sanctions targeting President Miguel Díaz-Canel and associates in June 2026, following the May indictment of former leader Raúl Castro over a 1996 plane incident. These measures coincide with an energy blockade contributing to blackouts and shortages on the island, alongside executive actions expanding restrictions and public statements referencing potential further steps. Traders assess roughly even odds of federal criminal charges against Díaz-Canel by year-end, reflecting the pattern of escalating Justice Department actions against Cuban officials but also the absence of confirmed charges or arrest warrants to date. Key variables include ongoing diplomatic signals, any new Treasury designations, and procedural timelines for indictments before December 31.