Trump’s second-term Cuba policy centers on maximum pressure through expanded sanctions, an oil blockade, and demands that President Miguel Díaz-Canel step down before any substantive progress, as conveyed by U.S. officials in March. Recent developments include new executive sanctions imposed on May 1 targeting regime figures, Trump’s May 12 statement that Cuba seeks help and talks will occur, and Cuban acceptance of limited humanitarian aid while rejecting broader U.S. terms. These moves align with the administration’s focus on economic coercion and regime change rather than direct leader-level engagement. No bilateral summit, call, or schedule involving Trump and Díaz-Canel has been announced, and Cuba has outlined red lines amid heightened tensions. Traders therefore price a direct conversation by June 30 at low odds, consistent with historical patterns of U.S. pressure campaigns prioritizing leverage over immediate presidential diplomacy.