When Ravi Gupta was a struggling high school student, he pulled Jon Lee Anderson’s biography of Che Guevara off his mom’s bookshelf—and it became the first book that truly grabbed him, shaping how he saw the world. That personal connection sparks a wide-ranging conversation about how Anderson’s globe-trotting childhood led him to report from the frontlines of history and build trust with everyone from warlords to world leaders. The episode traces Cuba’s dramatic ups and downs—from the economic collapse of the 1990s to Barack Obama’s brief attempt at reopening relations—and why the country now feels closer to crisis again. And it ends with an unforgettable twist: Anderson’s own unlikely role in uncovering what happened to Che Guevara after his death.
—> VOTE HERE or Where the School’s Went for Webby Awards
Best Health, Science, or Education Podcast
Is Cuba Next (New Yorker, March 2026)
The Devil They Know (New Yorker, July 1998)
Adventures of a Teen-Age Wharf Rat (New Yorker, January, 2024)
Jon Lee Anderson’s’ Che Guevara: A Revolutionary Life (1997)
Goodbye to All That (New York Review, July 1997)
Leave us a voicemail with your thoughts on the show: 201-305-0084
Follow The Branch on Instagram
Subscribe to Lost Debate on Apple
Subscribe to Lost Debate on Spotify
Listen to Where the Schools Went on Apple
Listen to Where the Schools Went on Spotify