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 (cfr.org/experts/james-m-lindsay), Mary and David Boies Distinguished Senior Fellow in U.S. Foreign Policy, CFR

Guest:

Will Freeman (cfr.org/experts/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 (nbcnews.com/world/cuba/cuba-pushes-sweeping-fr…)," NBC News, June 20, 2026

"July 11, 2021 Protests in Cuba (wola.org/2022/07/july-11-cuba-1-year-later)," WOLA, July 2022

"Miami Herald Investigation: GAESA's Secret Dollar Reserves (miamiherald.com/news/nation-world/world/americ…)," Miami Herald, August 6, 2025

For an episode transcript and show notes, visit The President’s Inbox at: cfr.org/podcasts/presidents-inbox/maximum-pres…

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.