FRESH AIR — “Will President Trump Act on His Threat to Take Cuba?”
A Conversation with Journalist John Lee Anderson
Aired: March 24, 2026
Host: Terry Gross (NPR)
Guest: John Lee Anderson (staff writer at the New Yorker, author, longtime Cuba observer)
Episode Overview
This episode of Fresh Air, hosted by Terry Gross, focuses on the escalating crisis between the United States and Cuba amid widespread turmoil in the region. With Donald Trump publicly threatening to “take Cuba” while ongoing conflicts engulf Iran and much of the Gulf, Cuba faces unprecedented economic, social, and political hardship. Renowned journalist John Lee Anderson, recently back from reporting on the ground in Cuba, discusses current conditions, the motivations and strategies on all sides, and what is at stake for Cubans and U.S. foreign policy.
Key Discussion Points and Insights
1. Trump’s Threats and Rhetoric Toward Cuba
- Trump said he would have “the honor of taking Cuba,” using dismissive and invasive language that sparked widespread offense in Cuba and among observers of U.S.-Cuba relations.
- Quote (Trump): “I think I could do anything I want with it. You want to know the truth? They're a very weakened nation right now." (02:10)
- Anderson responds with “dismay and shock” at the President’s language, noting that Cuban nationalism predates the revolution and runs deep.
- Quote (Anderson): “This kind of dismissive language is deeply humiliating, hurtful, and would get anyone’s back up on the island.” (02:46)
2. Why Cuba Now? U.S. Motivations Under Trump
- Cuba’s “undeveloped beachfront property” is described as a “real estate tycoon’s dream,” more valuable to an operator like Trump than traditional resources.
- Quote (Anderson): “For a real estate guy like Trump, Cuba is just bonanza waiting to happen.” (04:08)
- Trump’s business interests have previously scoped Cuba for possible development (golf courses, marinas), though no deals were struck. (05:49)
3. Conditions on the Ground in Cuba
- Cuba is in ruins: the electrical grid has collapsed, food and fuel are scarce, many have left, and economic activity has all but halted.
- Quote (Anderson): “The emptiness of the island is what struck me … now there was almost none [tourists]. … lights were often off … the electrical grid really has just fallen apart and with it virtually all public transport.” (06:19)
- Health care, once a Cuban point of pride, is in crisis, and outbreaks of mosquito-borne illnesses like chikungunya are rising. Even once-sterile cities are now dirty, with garbage piling up, furthering public health concerns.
- Quote (Anderson): “Now many of the doctors … have left because they just couldn’t survive on the government provided salaries of, you know, the equivalent of a few dollars a month … that’s just what’s happened.” (08:33)
4. Military Mobilization and Resistance
- In anticipation of a U.S. military invasion, Cuba is quietly mobilizing reserves and renewing training, following protocols rooted in decades-old defense doctrine.
- Quote (Anderson): “They have an action plan to defend that area in case of invasion … I would think it would be unwise to regard them as a spent force.” (13:29)
5. Internal Dissent and Revolutionary Fatigue
- Some former revolutionaries, once committed to the ideals of the Cuban project, express despair—willing to consider anything to “end” the current situation.
- Quote (Friend of Anderson): “I don’t care anymore how it happens, but this situation has to end.” (14:39)
- Anderson: “He even said, ‘Where’s Delta Force?’ … a bleak acknowledgment of where they are in history.” (14:58)
6. The Castro Family’s Enduring Influence
- Though official power has transferred, Raul Castro, now 94, exerts control. His relatives, including grandson Raulito and son Alejandro, remain pivotal behind the scenes.
- Details on negotiations involving family members and their meetings with U.S. officials, notably the role of Raulito in recent talks. (16:57–19:19)
- The Miami Cuban lobby strongly opposes any continuation of Castro family rule.
7. Venezuela’s Role and Its Decline
- Cuba’s economic collapse is profoundly linked to the loss of Venezuelan aid—fuel and supplies ceased after the U.S. overthrew Maduro.
- Quote (Anderson): “Venezuela has been the, in a sense, replace the Soviet Union, which had been the sponsor of Cuba, subsidized Cuba for 35 years.” (22:55)
- With Venezuelan and Mexican oil gone, Cuba’s fuel crisis is compounded.
8. U.S. Negotiations, Sanctions, and Hardliners
- Secretary of State Marco Rubio is leading behind-the-scenes U.S.-Cuba negotiations, pushing for economic and political reforms in exchange for humanitarian aid and oil.
- Rubio’s stance is more measured than some hardliners; he seeks “change in Cuba” but with gradual reforms, not a sudden transformation.
- Details the entanglement of U.S. law (Helms-Burton Act) in Cuba policy—a blockade only Congress can fully lift. (28:51)
- Quote (Anderson on Miami congressman): “He described it to me as like cancer. You know, sometimes chemo does a lot of harm to the body, but you get rid of the cancer. And that’s how he viewed the need for this kind of approach.” (28:51)
9. Humanitarian Missions and Distrust
- Aid tankers from international volunteers are met with skepticism inside Cuba due to government control and potential for inequitable distribution.
- U.S. officials direct aid through the Catholic Church as a way to bypass state mechanisms. (34:30–35:30)
10. The Next Generation of Castros: Sandro Castro
- Fidel’s grandson Sandro is a social media influencer, a marked shift from family austerity and a point of contention in Cuban society.
- Quote (Anderson): “He just does what he wants, which is sort of what an American kid would do … It’s interesting that one of the Castros has produced the first, you know, in-your-face, I say what I want, I do what I want person on social media. Isn’t that interesting?” (37:43, 37:50)
- His privilege allows him freedoms ordinary Cubans lack. (38:02–38:15)
11. Lessons from Afghanistan, Iraq, and U.S. Regime Change
- Drawing on his experience in Afghanistan, Anderson warns of the perils of “regime change”—failing to confer sovereignty and respect leads to disaster.
- Quote (Anderson): “If you show that much disdain and cultural divorce from the place you’re entering in a bellicose way as a warring party, then you know you’re not going to win them over … We’re just repeating the old cycle again and again … Regime change almost always [is] a catastrophic failure.” (39:28–43:00)
12. Che Guevara’s Legacy and Anderson’s Reporting
- Anderson’s deep research into Che Guevara’s life reveals the evolution of a figure from idealistic humanist to hardline revolutionary, and what is lost in that doctrinaire shift.
- Quote (Anderson): “The young Che Guevara was an incredibly open minded man … And to see him become small minded, doctrinaire, intransigent disappointed me.” (46:00)
- He ponders what might have happened if Che had lived longer and continued to evolve.
Notable Quotes & Moments (Timestamps)
- “[Trump:] I think I could do anything I want with [Cuba]. You want to know the truth? They're a very weakened nation right now.” (02:10)
- “[Anderson:] Dismay and shock just at the tone the man who is the President … used in referring to another country.” (02:46)
- “Cuba’s just bonanza waiting to happen.” (04:08)
- “The emptiness of the island is what struck me … people simply aren’t doing anything.” (06:19)
- “Many of the doctors … have left because they just couldn’t survive.” (08:33)
- “I would think it would be unwise to regard them as a spent force. … the anti-imperialist ethos is well grounded.” (13:29)
- “[Friend, former revolutionary:] I don’t care anymore how it happens, but this situation has to end.” (14:39)
- “It includes several large lawsuits by U.S. corporations. … It’s paved the way for lawsuits against the Cuban government for confiscated properties.” (28:51)
- “He described it to me as like cancer. You know, sometimes chemo does a lot of harm to the body, but you get rid of the cancer.” (28:51, paraphrased from Carlos Jimenez, Miami Congressman)
- “He just does what he wants, which is sort of what an American kid would do … one of the Castros has produced the first … I say what I want, I do what I want person on social media.” (37:43, 37:50)
- “Regime change almost always [is] a catastrophic failure.” (43:00)
- “The young Che Guevara was an incredibly open minded man … to see him become small minded, doctrinaire, intransigent disappointed me.” (46:00)
Important Timestamps
- 00:30 — Terry Gross introduces topic and guest John Lee Anderson
- 02:10 — Trump’s quote about taking Cuba
- 02:46 — Anderson’s reaction to Trump’s rhetoric
- 04:08 — Discussion of Cuba as real estate opportunity
- 06:19 — Anderson describes dire conditions in Cuba
- 08:33 — Impact on health care and medical brain drain
- 13:29 — Details of Cuban military readiness
- 14:39 — Former revolutionary’s despair and black humor
- 16:57 — Castro family's continued influence and back-channel negotiations
- 22:55 — Venezuela’s broken pipeline and its impact
- 25:59 — Rubio's approach and negotiating stance
- 28:51 — Helms-Burton Act and hardliner strategies
- 34:30 — Humanitarian supplies reach Cuba; concerns about distribution
- 35:46 — The new "influencer" Castro: Sandro Castro
- 39:28 — Lessons on U.S. regime change from Afghanistan and elsewhere
- 46:00 — Che Guevara’s transformation and Anderson’s personal reflections
Tone and Takeaways
- The conversation blends sobering, factual reporting with moments of black humor and personal reflection.
- Anderson’s on-the-ground perspective and extensive historical context offer a nuanced, skeptical view of American ambitions and the Cuban response.
- The overall mood is one of deep concern: for Cuba’s suffering people, for the cyclical failures of U.S. interventionism, and for the likelihood of further upheaval rather than genuine resolution.
This episode is a must-listen for anyone interested in U.S.–Cuba relations, humanitarian crises under sanctions, and the perils of regime change—past and present.