Podcast Summary: Big Take – "What Trump Wants in Cuba"

Date: March 24, 2026
Host: Sarah Holder (Bloomberg News)
Guests: Jim Wiss (Bloomberg Reporter on Cuba), Eric Martin (Bloomberg State Department and Foreign Policy Reporter)

Overview

This episode of Bloomberg's "The Big Take" explores the sharply escalating U.S. pressure on Cuba during President Donald Trump's second term. The focus is on the American strategy—political, economic, and potentially military—aimed at triggering profound change in Cuba's government. The discussion also analyzes the key role of Secretary of State Marco Rubio, the impacts on everyday Cubans, reactions from the Cuban diaspora, and what might come next as both countries reach a possible inflection point.

Key Discussion Points & Insights

1. Escalation of U.S. Policy Toward Cuba

• President Trump’s attention to Cuba has intensified in his second term.
• The appointment of Marco Rubio (son of Cuban immigrants, Miami political base) as Secretary of State signaled a renewed hardline posture. ([02:15])
  • Quote: “The naming of Marco Rubio...was a strong signal that the communist governments in the Western Hemisphere were going to be a big focus of attention for the administration right out of the gate.” – Eric Martin ([02:15])
• Rubio led the push to re-designate Cuba as a state sponsor of terrorism, reversing Obama-era thawing efforts. ([02:40])

2. The Oil Blockade and Knock-On Effects

• After the US ousted Venezuelan President Nicolas Maduro in January, a key source of Cuban oil was severed.
• Imposed American oil blockade has devastated Cuba’s energy and economic sectors, causing week-long blackouts and severe hardship. ([03:11], [03:30])
  • Quote: “Some nights the entire island goes dark.” – Sarah Holder ([03:30])

3. Cuba at a Breaking Point

• Cuba is experiencing its worst crisis since the "special period" following the fall of the Soviet Union. The government has acknowledged being unable to deliver food and aid due to lack of fuel. ([04:09], [04:47], [08:04])
  • Quote: “It’s a huge moment... 67 years and it's looking really unclear if this one-party system is going to survive the year.” – Jim Wiss ([04:09])
  • Quote: “Industry is grinding to a halt, and resorts... have had to shut down because there’s not enough fuel. ...Hunger is real.” – Jim Wiss ([08:04])

4. The Venezuela-Cuba Relationship: Critical Context

• Historical context: Venezuela became Cuba's lifeline after the Soviet Union’s collapse, sending oil in exchange for Cuban expertise and labor.
• The U.S. cutoff of Venezuelan oil to Cuba—and threats against other suppliers like Mexico—has left Cuba isolated. ([05:25], [07:03])

5. Popular Dissent and Government Survival

• Unconfirmed reports of deaths in hospitals, more visible protests including attacks on Communist Party offices, and general dissatisfaction toward both governments. ([09:02])
• Outright demonstrations are banned, but discontent is surfacing.
  • Quote: “There’s a lot of dissatisfaction on the street, some of it aimed at Washington, some of it aimed at the local authorities.” – Jim Wiss ([09:02])

6. U.S. Goals: Dominance and Democratic Change

• The Trump administration’s national security strategy, released in December, focuses on reasserting U.S. dominance in the Western Hemisphere and preventing influence from nations like China.
• Nostalgia and strategic interest among the Cuban-American exile community in Florida further shape policy. ([09:49])
  • Quote: “This is an administration that... is very focused on asserting US preeminence and dominance in the Western Hemisphere.” – Eric Martin ([09:49])

7. Diaspora and Expatriate Reactions

• The Cuban diaspora shows interest in investing and changing Cuba, especially with recent Cuban legislation allowing exiles to participate in the economy.
• However, skepticism abounds due to Cuban government history of expropriation and complicated legal realities. ([11:08], [17:38])
  • Quote: “There’s a lot of skepticism in the exile community about putting money into Cuba... this is not nearly enough for what people need to see.” – Eric Martin ([17:38])

8. Cuban Government’s Response

• Cuban President Miguel Díaz-Canel has publicly acknowledged U.S. actions are hurting the country; describes U.S policies as "collective punishment."
• Simultaneously, the government insists it will not negotiate over who leads Cuba, maintaining a tone of defiance. ([12:13])
  • Quote: “They keep saying that... we’re not willing to discuss who leads our country.” – Jim Wiss ([12:13])

9. Prospects for Diplomacy, Intervention, or Economic Takeover

• U.S. and Cuban officials are engaged in talks. The Trump administration reportedly seeks the removal of Díaz-Canel, favoring Raul Castro's grandson ("Raulito/El Congrejo") as a possible leader more open to compromise and markets. ([15:42])
• U.S. strategy includes fostering Cuba’s private sector to trigger political opening, reminiscent of Gorbachev-era reforms in the Soviet Union. ([15:42])
  • Quote: “The US is looking to use economic pressure... to foster this private sector, which they see as leading to a political opening in Cuba.” – Eric Martin ([15:42])
• The administration weighs three options:
  • Diplomacy/deal-making (ongoing),
  • Military action ("friendly takeover" rhetoric, but no preparations observed yet),
  • Economic pressure to make Cuba dependent on the U.S. and force political changes.
• Much depends on the outcome of current U.S. involvement in Iran; a resolution there may shift more focus to Cuba. ([19:04], [20:11])
  • Quote: “He’s repeatedly said Cuba would be dealt with after Iran.” – Eric Martin ([20:11])

10. Historic Stakes and Latin American Perceptions

• Any U.S.-enforced change in Cuba would have massive historical significance after decades of failed U.S. efforts.
  • Quote: “Ever since Kennedy, successive U.S. Presidents have been trying to... force a change, negotiate a change... It’s an incredible story of kind of political survival in Cuba... if Trump was the one to do it, that would be incredibly significant.” – Jim Wiss ([21:15])
• The collapse of Cuba’s one-party system would reshape regional politics and fuel leftwing nostalgia throughout Latin America.

Notable Quotes & Memorable Moments (with Timestamps)

• “Taking Cuba in some form. Yeah.” – Jim Wiss ([03:34])
• "Some nights the entire island goes dark." – Sarah Holder ([03:30])
• “Industry is grinding to a halt, and resorts... have had to shut down because there’s not enough fuel. ...Hunger is real.” – Jim Wiss ([08:04])
• "Ever since Kennedy, successive U.S. presidents have been trying to either force a change, negotiate a change... And it’s never happened." – Jim Wiss ([21:15])
• “He’s repeatedly said Cuba would be dealt with after Iran.” – Eric Martin ([20:11])

Key Timestamps

• 01:46 – Episode content begins, setting stage with Trump’s renewed interest in Cuba
• 02:15 – Analysis of Marco Rubio’s impact as Secretary of State
• 03:11 – US-mandated oil blockade, economic and social impacts described
• 05:25 – Deep dive into Cuba-Venezuela alliance and its breakdown
• 08:04 – Humanitarian impacts: blackouts, hunger, hospital crises
• 09:49 – U.S. strategy: Western Hemisphere dominance, Florida exiles' influence
• 12:13 – Cuban government response: public pain, private intransigence
• 15:42 – Current state of diplomacy: who’s negotiating, what’s at stake
• 17:38 – Cuban-American investment skepticism
• 18:31 – Military intervention as a possibility, administration’s signals
• 20:11 – Trump’s sequencing: Iran first, then Cuba
• 21:15 – Historical significance and regional implications

Conclusion

This episode paints a picture of unprecedented U.S. pressure on Cuba, intersecting humanitarian crisis, and the real possibility of regime change under President Trump’s administration. The voices of Bloomberg’s foreign policy experts capture both the human impact on Cuba’s population and the political ambition animating American strategy. The collapse or transformation of Cuba’s government under pressure from Washington would leave lasting ripples across Latin America and American political history.