Cuba Libre?

Lost Debate

The Branch

News, Society & Culture, Politics

4.6 • 607 Ratings

🗓️ 16 April 2026

⏱️ 52 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 for Where the School’s Went for Best Health, Science, or Education Podcast ------- Leave us a voicemail with your thoughts on the show! 201-305-0084⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow Ravi at @RaviMGupta Notes from this episode are also available on Substack: https://thelostdebate.substack.com/ Read more from Ravi on Substack: https://realravigupta.substack.com Follow The Branch at @thebranchmedia Listen to more episodes of Lost Debate on Apple: https://podcasts.apple.com/us/podcast/the-lost-debate/id1591300785 Listen to more episodes of Lost Debate on Spotify: https://open.spotify.com/show/7xR9pch9DrQDiZfGB5oF0F Listen to Where the Schools Went: https://thebranchmedia.org/show/where-the-schools-went/

Transcript

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0:00.0	Welcome to the Lost Debata Show for Political Eclectics. I'm Ravi Gupta and holy smokes, this was an all-time interview. I got a chance to interview somebody who I have wanted to talk to for a very, very long time. John Lee Anderson, who is a reporter for the New Yorker, who has chronicled from every war zone you could ever imagine. But I first was introduced to his work because he wrote
0:21.8	a seminal biography of Che Guevara that is comprehensive to say the least captures, you know,
0:28.7	what made Che Guevara such a mythical figure, also was unsparing about Chez's flaws. It is an
0:35.5	incredible read. One of my favorite books I've ever read in just a heroic act of journalism.
0:40.9	And John Lee Anderson actually lived in Cuba in the 90s to write that book and has been reporting
0:46.2	on Cuba and has written numerous articles about Cuba's evolution since the 90s.
0:52.9	And he's also been all over the place. Every, you know, Afghanistan,
0:56.1	I think Syria, Liberia, et cetera. And we talk a little bit about John and what makes him tick as a
1:03.2	writer and how he gets people to open up to him. We also talk about, we spent a lot of time talking about
1:07.5	Cuba now and what the future of this island is and what are the
1:12.0	sort of various risks and opportunities. And then he tells an amazing story at the end about
1:17.4	Che Guevara, which is definitely worth waiting for. But before we get there, if you're listening
1:22.4	to this on Thursday, April 16th, and it's know, it's before midnight, wherever you are,
1:34.1	please click on the link in the show notes for voting for just one category of the Webby Awards.
1:35.7	We're up for the People's Choice Awards.
1:39.2	We're still a couple percentage points behind in the People's Choice Awards. So we're number two in the voting.
1:41.4	So please just pause this.
1:42.7	Before you listen to anything else, click on that link,
1:45.6	just vote for where the schools went, our podcast about New Orleans. Do me a huge favor. We don't
1:50.9	bother you for ads or anything like that. If everybody listens to this, clicks on that link and votes,
1:54.9	we will go from two to number one. It's a huge accolade for our team and really helps us out
2:00.0	as we continue to try to,
	...

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