Maximum Pressure on Cuba, With Will Freeman

This episode unpacks how the Trump administration's maximum pressure campaign is accelerating Cuba's economic collapse and what a firsthand trip to the country reveals about life amidst the crisis. Host: James M. Lindsay, Mary and David Boies Distinguished Senior Fellow in U.S. Foreign Policy, CFR Guest: Will Freeman, Fellow for Latin America Studies, CFR We Discuss: What the Trump administration is ultimately seeking to accomplish with its Cuba policy. How secondary sanctions differ from the existing trade embargo. What life on the ground in Cuba looks like today, with a mass economic crisis including widespread malnutrition and near-total electricity blackouts. Whether ordinary Cubans blame the United States or their own government for the crisis. Whether Cuba's government is attempting to pivot toward a China-style state capitalist system. What Grupo de Administración Empresarial S.A. (GAESA) is, why it controls so much of Cuba's economy, and who actually benefits from it. Whether the Trump administration's pressure is targeting GAESA directly. Why a Venezuela-style external coup or regime collapse is harder to engineer in Cuba. Mentioned on the Episode: "Cuba's 176 Market-Liberalization Measures," NBC News, June 20, 2026 "July 11, 2021 Protests in Cuba," WOLA, July 2022 "Miami Herald Investigation: GAESA's Secret Dollar Reserves," Miami Herald, August 6, 2025 For an episode transcript and show notes, visit The President’s Inbox at: https://www.cfr.org/podcasts/presidents-inbox/maximum-pressure-on-cuba Opinions expressed on The President’s Inbox are solely those of the host or guests, not of CFR, which takes no institutional positions on matters of policy.