Is Cuba Nearing an Inflection Point?

President Trump is ramping up economic pressure on Cuba and has instructed U.S. intelligence agencies to find a new leader who could work with the United States – like Delcy Rodriguez in Venezuela. Christopher Hernandez Roy and William LeoGrande join Will to discuss how the Trump administration’s strategy on Cuba is evolving, how Cuban leaders are responding, and if we are nearing an inflection point. State of Play audience survey Christopher Hernandez-Roy, Mark Cancian, and Henry Ziemer, "The Next Caribbean Crisis? Assessing U.S. Military Options Toward Cuba," CSIS, June 3, 2026. William M. LeoGrande and Peter Kornbluh, "Is the United States on the Verge of Military Intervention in Cuba?" Foreign Policy, May 22, 2026. Christopher Hernandez-Roy et al, "Preparing for the Consequences of Collapse in Cuba," CSIS, April 9, 2026. William M. LeoGrande and Peter Kornbluh, Back Channel to Cuba: The Hidden History of Negotiations between Washington and Havana, University of North Carolina Press, 2014.