For more than six decades, the United States has tried to topple the regime in Cuba. After ousting President Nicolás Maduro of Venezuela, who was one of Cuba’s closest allies, the Trump administration is closer than ever to forcing radical change on the island. The New York Times reporters Frances Robles and Michael Crowley discuss how the latest escalation is pushing Cuba to the brink, and whether this time the United States will get what it wants.  Guest: • Frances Robles (https://www.nytimes.com/by/frances-robles) , an international correspondent covering Latin America and the Caribbean for The New York Times. • Michael Crowley (https://www.nytimes.com/by/michael-crowley) , a reporter covering the State Department and U.S. foreign policy for The New York Times. Background reading:  • Cuba’s government has lasted 67 years. Will it fall under Mr. Trump (https://www.nytimes.com/2026/02/08/world/americas/cuba-communist-government-trump.html) ? • Can Cuba survive without Venezuela’s oil (https://www.nytimes.com/2026/01/17/world/americas/cuba-venezuela-oil-power-blackouts.html) ? Photo: Yamil Lage/Agence France-Presse — Getty Images For more information on today’s episode, visit nytimes.com/thedaily (http://nytimes.com/thedaily?smid=pc-thedaily) . Transcripts of each episode will be made available by the next workday.  Subscribe today at nytimes.com/podcasts (http://nytimes.com/podcasts) or on Apple Podcasts and Spotify. You can also subscribe via your favorite podcast app here https://www.nytimes.com/activate-access/audio?source=podcatcher. For more podcasts and narrated articles, download The New York Times app at nytimes.com/app.