Will President Trump act on his threat to take Cuba? - Fresh Air Recap

Podcast: Fresh Air

Published: 2026-03-24T17:45:34.000Z

Duration: 2683

Guests: John Lee Anderson

What Happened

President Trump's threat to 'take Cuba' comes at a time when the island nation is grappling with severe economic challenges. The power grid is failing, a significant portion of the population is emigrating, and shortages of food, fuel, and medical supplies are rampant. These shortages have led to malnutrition and outbreaks of mosquito-borne illnesses.

Venezuela, once a key supplier of oil to Cuba, has ceased shipments following the U.S. arrest of Venezuelan President Nicolas Maduro, exacerbating Cuba's economic woes. John Lee Anderson points out that the cessation of oil shipments has significantly impacted Cuba's economy, leaving it more vulnerable to external pressures.

The Trump Organization had previously explored potential real estate developments in Cuba, such as golf courses and marinas, in 2013. This interest in Cuba's undeveloped tourism potential aligns with current discussions, raising questions about real estate interests influencing U.S. policy.

Cuba's military, seen as a strong entity with an anti-imperialist ethos, is preparing for a potential U.S. invasion. Raul Castro, despite his advanced age, remains a significant power figure in Cuba, while his grandson, Sandro, diverges from family tradition as a social media influencer and bar owner.

Marco Rubio, a Cuban-American politician, is involved in negotiations with Cuba, advocating for change but stopping short of immediate regime change. The Helms-Burton Act, which makes the U.S. embargo on Cuba permanent unless lifted by Congress, plays a crucial role in these discussions.

Humanitarian missions are sending tankers with supplies to Cuba, aiming to alleviate the shortages. The U.S. ambassador to Cuba has distributed food aid through the Catholic Church, following directives from Rubio to avoid government involvement.

John Lee Anderson, a staff writer at The New Yorker, draws parallels between Cuba and Afghanistan, noting that American-style regime change often fails due to cultural ignorance and lack of genuine investment. He cites his book 'To Lose a War: The Fall and Rise of the Taliban' to illustrate lessons learned from the U.S. intervention in Afghanistan.

Anderson also discusses Che Guevara's transformation from a humanistic figure to a doctrinaire Marxist-Leninist after witnessing a CIA-backed overthrow in Guatemala. He notes that Guevara's views continued to evolve before his death, adding depth to the historical context of U.S.-Cuba relations.

Key Insights

• Cuba's economy is heavily impacted by the cessation of Venezuelan oil shipments, leaving it vulnerable to external pressures and exacerbating existing shortages.
• President Trump's interest in Cuba may be influenced by the country's undeveloped tourism potential, as the Trump Organization previously explored real estate developments there.
• Cuba's military is preparing for a potential U.S. invasion, maintaining a strong anti-imperialist stance despite internal challenges and leadership changes.
• American-style regime change often fails due to cultural ignorance and lack of investment, as demonstrated by the U.S. experience in Afghanistan, which John Lee Anderson uses as a parallel to potential actions in Cuba.