Will Trump & Co. Go After Cuba Next? with Jon Lee Anderson

In this episode of 'Why Is This Happening?', host Chris Hayes explores the escalating crisis in Cuba, driven by a new U.S. energy blockade under Donald Trump's administration. Following the abduction of Venezuelan President Nicolás Maduro and the severing of Venezuela's oil supply to Cuba, the U.S. has imposed a de facto fuel embargo, cutting off all foreign oil shipments. With Cuba producing only 40,000 barrels a day but needing 100,000, the nation faces a humanitarian catastrophe: collapsing power grids, no public transportation, stalled medical procedures, rampant disease, and widespread garbage accumulation. Veteran journalist Jon Lee Anderson, author of 'Is Cuba Next?' in The New Yorker, provides historical context, tracing Cuba’s economic struggles from the Soviet collapse through the stabilizing role of Hugo Chávez’s Venezuela. He explains how Cuba’s fragile state capitalism—marked by periodic reforms and crackdowns—has failed to deliver systemic change, leaving the country vulnerable to external pressure. Hayes and Anderson debate whether the U.S. strategy is truly about regime change or simply a transactional power play to extract leverage, with Trump’s provocative rhetoric echoing his 'Access Hollywood' past. The episode reveals deep contradictions: while Cuban-Americans in Miami demand regime change, many also rely on remittances and flights to support family, creating moral and political tension. The Cuban government, now mobilizing militarily and preparing for a prolonged standoff, appears to be betting on a U.S. political shift in November, hoping the Trump administration’s faltering foreign policy in Iran will limit its ability to act in Cuba. The risk of civil unrest or a humanitarian disaster looms, but a full-scale military invasion remains unlikely unless chaos erupts. Key takeaways include: 1) Cutting off fossil fuels to a nation with no domestic production is a deliberate strategy to induce collapse, not just economic hardship. 2) The U.S. is attempting to turn Cuba into a dependent client state through economic coercion, not liberation. 3) Cuban resilience is rooted in a deep historical narrative of resistance, which the current U.S. administration appears to misunderstand. 4) The Cuban government is likely playing a long game, using the crisis to stall and survive until the next U.S. election. 5) The humanitarian cost is already severe, with hospitals, water systems, and sanitation failing, and disease spreading unchecked. 6) The role of figures like Marco Rubio and Carlos Jiménez highlights the deep ideological rift within the Cuban-American community. 7) The U.S. strategy may be more about political theater and domestic optics than real foreign policy. 8) The risk of unintended consequences—such as a Haitian-style collapse—is real and could force a U.S. response, even if not desired.