Uploaded July 2026 | Updated September 2026, 3 weeks ago
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:
1. What the Trump administration is ultimately seeking to accomplish with its Cuba policy.
2. How secondary sanctions differ from the existing trade embargo.
3. What life on the ground in Cuba looks like today, with a mass economic crisis including widespread malnutrition and near-total electricity blackouts.
4. Whether ordinary Cubans blame the United States or their own government for the crisis.
5. Whether Cuba's government is attempting to pivot toward a China-style state capitalist system.
6. What Grupo de Administración Empresarial S.A. (GAESA) is, why it controls so much of Cuba's economy, and who actually benefits from it.
7. Whether the Trump administration's pressure is targeting GAESA directly.
8. Why a Venezuela-style external coup or regime collapse is harder to engineer in Cuba.
00:00 - Introduction to The President’s Inbox
02:14 - Cuba’s Economic Crisis and Protests
05:42 - U.S. Sanctions and Maximum Pressure
08:15 - Human Rights and Political Prisoners
11:03 - Role of Russia and China in Cuba
13:54 - Impact of the State Sponsor of Terrorism List
16:30 - Migration Trends and U.S. Border Security
19:15 - Cuban-American Politics in South Florida
22:04 - Havana’s Diplomatic Strategy
24:52 - Humanitarian Aid vs. Regime Stability
27:18 - Assessing the Embargo’s Effectiveness
30:05 - Geopolitics of Latin American Alliances
31:45 - Future of U.S.-Cuba Relations
32:10 - Closing Remarks and Key Takeaways
Find us
Maximum Pressure on Cuba, With Will Freeman - cfr.org/podcasts/presidents-inbox/maximum-pressure-on-cuba
The President’s Inbox - cfr.org/podcasts/presidents-inbox
Apple Podcasts - podcasts.apple.com/us/podcast/the-presidents-inbox/id1172546141
Spotify - open.spotify.com/show/65u6jcFyV5BnlVhhzSi7UJ
Related Content
Cuba's 176 Market-Liberalization Measures - nbcnews.com/world/cuba/cuba-pushes-sweeping-free-market-reforms-biggest-economic-shift-revolu-rcna350933
July 11, 2021 Protests in Cuba - wola.org/2022/07/july-11-cuba-1-year-later
Miami Herald Investigation: GAESA's Secret Dollar Reserves - miamiherald.com/news/nation-world/world/americas/cuba/article311494641.html
Opinions expressed on The President’s Inbox are solely those of the host or our guests, not of CFR, which takes no institutional positions on matters of policy.
Subscribe to our channel: youtube.com/user/cfr
The Council on Foreign Relations (CFR) is an independent, nonpartisan membership organization, think tank, and publisher.
Visit the CFR website: cfr.org
Follow CFR on X: https://x.com/cfr_org
Follow CFR on Facebook: facebook.com/councilonforeignrelations
Follow CFR on Instagram: @CFR_org
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:
1. What the Trump administration is ultimately seeking to accomplish with its Cuba policy.
2. How secondary sanctions differ from the existing trade embargo.
3. What life on the ground in Cuba looks like today, with a mass economic crisis including widespread malnutrition and near-total electricity blackouts.
4. Whether ordinary Cubans blame the United States or their own government for the crisis.
5. Whether Cuba's government is attempting to pivot toward a China-style state capitalist system.
6. What Grupo de Administración Empresarial S.A. (GAESA) is, why it controls so much of Cuba's economy, and who actually benefits from it.
7. Whether the Trump administration's pressure is targeting GAESA directly.
8. Why a Venezuela-style external coup or regime collapse is harder to engineer in Cuba.
00:00 - Introduction to The President’s Inbox
02:14 - Cuba’s Economic Crisis and Protests
05:42 - U.S. Sanctions and Maximum Pressure
08:15 - Human Rights and Political Prisoners
11:03 - Role of Russia and China in Cuba
13:54 - Impact of the State Sponsor of Terrorism List
16:30 - Migration Trends and U.S. Border Security
19:15 - Cuban-American Politics in South Florida
22:04 - Havana’s Diplomatic Strategy
24:52 - Humanitarian Aid vs. Regime Stability
27:18 - Assessing the Embargo’s Effectiveness
30:05 - Geopolitics of Latin American Alliances
31:45 - Future of U.S.-Cuba Relations
32:10 - Closing Remarks and Key Takeaways
Find us
Maximum Pressure on Cuba, With Will Freeman - cfr.org/podcasts/presidents-inbox/maximum-pressure-on-cuba
The President’s Inbox - cfr.org/podcasts/presidents-inbox
Apple Podcasts - podcasts.apple.com/us/podcast/the-presidents-inbox/id1172546141
Spotify - open.spotify.com/show/65u6jcFyV5BnlVhhzSi7UJ
Related Content
Cuba's 176 Market-Liberalization Measures - nbcnews.com/world/cuba/cuba-pushes-sweeping-free-market-reforms-biggest-economic-shift-revolu-rcna350933
July 11, 2021 Protests in Cuba - wola.org/2022/07/july-11-cuba-1-year-later
Miami Herald Investigation: GAESA's Secret Dollar Reserves - miamiherald.com/news/nation-world/world/americas/cuba/article311494641.html
Opinions expressed on The President’s Inbox are solely those of the host or our guests, not of CFR, which takes no institutional positions on matters of policy.
Subscribe to our channel: youtube.com/user/cfr
The Council on Foreign Relations (CFR) is an independent, nonpartisan membership organization, think tank, and publisher.
Visit the CFR website: cfr.org
Follow CFR on X: https://x.com/cfr_org
Follow CFR on Facebook: facebook.com/councilonforeignrelations
Follow CFR on Instagram: @CFR_org
