The Daily – “After Venezuela, Is Cuba Next?”

Date: February 17, 2026
Hosts: Natalie Kitroeff
Guests: Frances Robles (NYT reporter, Cuba specialist), Michael Crowley (NYT foreign policy reporter)

Overview

This episode analyzes the unprecedented crisis facing Cuba after decades of U.S. efforts to topple its regime. With Venezuela—a critical ally—now out of the picture, and intensified U.S. pressure under President Trump, the country may finally be at a breaking point. The hosts and reporters explore what's different this time, what U.S. policy hopes to achieve, and the risks and possible outcomes for Cuba and the region.

Key Discussion Points & Insights

1. A New Crisis—Is This Time Different?

(00:17–04:28)

• Host Natalie Kitroeff opens by noting “this moment feels different” compared to Cuba’s past crises.
• Frances Robles (“Frenchie”), who has covered Cuba since 1993, agrees:
  Quote (02:17):

  “This time, all the people I interview…they all say the same thing. They say, ‘You know what? This time it might actually be true.’ And the word you hear over and over again is ‘unsustainable.’ This current situation in Cuba is unsustainable.”

• The trigger: Cuba used to import 60% of its oil from Venezuela and Mexico. Both have stopped shipments under U.S. pressure, leading to:
  • Acute fuel shortages
  • Intermittent public transportation and reduced hospital services
  • Restricted access to banks, curtailed school hours
  • A collapsing car business and looming food delivery breakdowns

Quote (03:55):

"They're announcing that banks will only be open by certain days…They're going to get to a point where they don't have the gasoline to deliver food to the store." – Frances Robles

2. The Long Saga: U.S. Efforts to Topple Cuba's Regime

(04:28–11:44)

• The U.S. government, for over 60 years, has tried every tactic—from embargoes to invasions—to force regime change in Cuba.
  • The embargo began after the Castro government seized U.S. assets.
  • The U.S. imposed near total isolation; the 1962 Cuban Missile Crisis escalated tensions.
  • CIA assassination attempts and periodic release valves—mass migration events—helped the Cuban regime manage internal unrest (e.g., the Mariel boatlift of 1980). Quote (07:33):

"[The U.S.] almost went to nuclear war with Cuba because it was discovered that Cuba had allowed Russia to place nuclear missiles on the island." – Frances Robles

• Migration as a tool:

  "Whenever things got too hot…Fidel Castro would open the doors and let people out. It was an escape valve." – Frances Robles (08:08)

3. How Cuba Survived—And What Changed

(09:47–14:04)

• Soviet Union collapse (1991) launched Cuba’s “special period”—severe shortages, more migration, but not regime collapse.
• Cuba's survival strategies:
  • Acceptance of periodic crisis and normalization of suffering
  • Reliance on Venezuela for economic and resource support (post-Soviet era)
  • Opening to tourism during the Obama administration, with hopes that economic liberalization would drive change—but the regime resisted, fearing it was a "Trojan horse"
    • Obama’s efforts: expand travel/business, encourage exposure to capitalism
    • Cuban government: limited these efforts, stalling broad reform

Quote (13:23):

"The idea from the Obama administration at the time was...we should try something else. And that something else should be exposing Cubans to the benefits of capitalism." – Natalie Kitroeff

• Trump reversed Obama’s opening; reinstated strict sanctions, travel, and business restrictions—the tactic was back to "sticks," applying pressure and isolation

4. The Trump Administration’s Calculated Pressure

(16:44–21:57)

• Michael Crowley explains the Trump administration’s new intensity, largely driven by Marco Rubio, who made toppling the Cuban regime a key mission.
  • Rubio, as Secretary of State/National Security Advisor, connects the toppling of Venezuela’s Maduro to isolating Cuba and cutting off oil supplies.
  • Trump's policies included tariffs and threats to other countries supplying oil to Cuba—Mexico, despite ideological alignment, stopped oil exports under pressure.

Quote (17:02):

"I think it's important to understand how much this is coming from Marco Rubio...we may be approaching an end game that Rubio has worked towards for decades now." – Michael Crowley

Quote (22:46):

"Mexico had actually overtaken Venezuela recently as the island's top supplier. So that's the second major supplier to the Cuban government that has stopped sending oil just this year." – Michael Crowley

5. Risks, Repercussions, and What’s Next

(23:52–28:17)

• The U.S. goal: force a humanitarian and economic crisis so severe the regime collapses—with hopes of a "soft landing" or negotiated transition.
• Major risks:
  • Cuba is a “monolithic, brittle political system” with virtually no organized opposition.
  • Regime collapse without a clear alternative could mean chaos, violence, and mass migration toward Florida.
  • Rubio and Trump’s best-case scenario is finding a negotiator/“Delsey Rodriguez figure” within the Cuban regime—but experts say this is "a fool's errand."
  • Cuba’s leadership is deeply experienced in playing for time; agreeing to any U.S.-backed transition would be seen, internally, as suicide.

Quote (24:34):

"It’s not easy...You risk total chaos, violence, mass migration from Cuba toward Florida—a lot of conditions that would put the Trump administration in a very uncomfortable position..." – Michael Crowley

Quote (26:46):

"It’s very unlikely you have somebody who would be willing to kind of step out...and allow themselves to be seen as a sort of American puppet...there’s just going to be very little of that in Cuba." – Michael Crowley

6. What Does Trump Actually Want?

(28:56–30:33)

• For Trump, toppling Cuba’s government may not be a central concern of most Americans, but if successful, it would be a historic foreign policy win outshining predecessors back to Eisenhower. Quote (29:25):

  "If President Trump were to bring down the communist government of Cuba...I really think that would be widely regarded...as a historic triumph. He will have solved a foreign policy problem that many presidents before him were stymied by." – Michael Crowley

Notable Quotes & Memorable Moments

1. Frenchie on Cuba’s endurance:

   “They've been saying this for 60 years, that this is the last year of the Cuban regime. But then this time...they all say, ‘You know what? This time it might actually be true.’” (02:15)

2. On Cuba’s escape valve:

   "Whenever things got too hot...Fidel Castro would open the doors and let people out. It was an escape valve." – Frances Robles (08:08)

3. On the cycle of U.S. policy:

   “Everybody else is trying to suffocate Cuba to get them to fold. [Obama’s] like, you know what? We’re going to do the opposite.” – Frances Robles (12:37)

4. On the personal nature of Rubio’s crusade:

   “This is at the core of his personal and political identity...” – Michael Crowley (19:25)

5. On the risks of a hard collapse:

   “If you bring down the entire government without something to replace it, you risk total chaos, violence, mass migration from Cuba toward Florida...” – Michael Crowley (24:34)

6. On the magnitude of regime change:

   “If [Trump] were able to do it without destroying Cuba along the way...that would be widely regarded...as a historic triumph.” – Michael Crowley (29:25)

Timeline of Important Segments

• 00:17–04:28: Analyzing the present crisis—what’s unsustainable in Cuba now
• 04:28–11:44: History of U.S.-Cuban animosity, embargo, and migration as a pressure valve
• 11:44–14:04: How Cuba survived without the USSR, pivot to Venezuela and tourism
• 14:04–15:14: U.S. policy whiplash—Obama’s opening, Trump’s renewed crackdown
• 16:44–23:22: Rubio's role, link to Venezuela, oil supply crisis, Mexico’s reluctant shift
• 23:22–26:46: Risks of "smashing the system," potential for chaos, soft-landing scenarios explored
• 28:56–30:33: Trump's possible motives, the prize of toppling Cuba in U.S. foreign policy

Tone

• Measured, deeply reported, historical context
• Skeptical but open-minded to the prospect that this time might be different
• Empathetic regarding the hardship endured by ordinary Cubans

Conclusion

This episode offers a comprehensive look at Cuba’s current crisis, why it may be unique, and the historical and political strategy behind U.S. pressure. It smartly situates today's events within the arc of U.S.-Cuba relations, explores how policy choices echo and diverge from the past, and leaves listeners with a sense of both the fragility and endurance of the Cuban regime, the stakes for U.S. policymakers, and the looming, unpredictable risks ahead.