Trump's second-term maximum pressure campaign has intensified economic isolation of Cuba through reimposed sanctions, a renewed state sponsor of terrorism designation, and January 2026 executive orders authorizing tariffs on third countries supplying oil after the U.S. capture of Venezuela's Maduro cut Havana's primary energy lifeline. Subsequent May indictments of Raúl Castro and expanded sanctions on regime officials, combined with naval and troop positioning in the Caribbean, have fueled speculation of Venezuela-style action. However, administration statements have also referenced potential negotiations or regime collapse without direct intervention, and no offensive military operations have commenced by mid-2026. Traders price the low odds of an invasion this year on the continued emphasis on sanctions, legal measures, and diplomatic leverage over kinetic escalation.