Book Recap #38- Silman’s Chess Odyssey + Stories from a Former Student with Gaurav Datta

Perpetual Chess Podcast

Perpetual Chess LLC

Leisure, Sports, Hobbies

4.8 • 706 Ratings

🗓️ 24 March 2026

⏱️ 82 minutes

🔗️ Recording | iTunes | RSS

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Summary

The Perpetual Chess book discussion series Chess Books Recaptured returns with a personal, funny, and heartfelt episode. Gaurav Datta, a longtime student and close friend of IM Jeremy Silman, joins me to discuss Silman’s Chess Odyssey: Cracked Grandmaster Tales, Legendary Players, & Instructions and Musings. This memoir and collection of writing was Silman’s final work, and it beautifully captures his deep and enduring love for chess. As Gaurav shares, he was an ordinary club player who repeatedly emailed Silman until Jeremy reluctantly agreed to take him on as a student in the late 1990s. What began as lessons soon turned into a decades-long friendship. Jeremy did not care much about Gaurav’s rating, but he appreciated his sense of humor and his ability to tell interesting stories. Throughout the conversation, Gaurav interweaves touching and often hilarious personal memories with insights from the book, offering a glimpse into Silman’s life and teaching philosophy. I greatly enjoyed reading Silman’s Chess Odyssey, and hearing Gaurav’s stories added a whole new dimension to understanding one of chess’s most beloved teachers. 0:00 Intro + overview of Silman’s Chess Odyssey Thanks to our sponsors, Chessable.com. Check out IM Jeremy SIlman’s vast catalog of courses here: https://www.chessable.com/author/Jeremy_Silman/5:48 Guest intro: Gaurav Datta (long-time student & friend of Jeremy Silman) 7:00 How Gaurav discovered Silman, early struggles, and first meeting12:30 What lessons with Silman were really like (stories, life, chess) 18:20 Chess as art: Silman’s core philosophy22:40 Training methods: studying master games & subtle ideas Mentioned: IM Erik Kislik, NM Steve Brandwein 28:00 Gambling struggles, life setbacks, and returning to chess 33:00 Silman’s personality: stories, Japan, boxing & unique interests 38:40 Final years, illness, and completing his last book Mentioned: Autobiography of a Goat 51:30 Key lessons: play for beauty, not rating + lasting impact 1:15:00- Thanks so much to Gaurav for sharing his amazing stories! Here is how you can reach him: Email- gdatta at gmail.com Chess.com- https://www.chess.com/member/olddirtypatzer Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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1:33.9	Hello, everyone and welcome back to perpetual chess. It has been a good while since I've done a book recap. There was a period where I was churning these out almost every month. I don't know how I managed to do that, but these days, they're an increasingly rare sighting, but we had the opportunity to do a recap of Jeremy Soman's Chess Odyssey. Of course, he's a beloved figure by the chess community at large and by myself and many listeners of this podcast. He's unfortunately no longer with us, but he's left so many,
2:01.6	so much great and instructive writing behind. I, of course, have done a couple recaps of
2:07.0	Jeremy Sillman's prior works, and you also can hear a reminisce that I did with his good
2:13.8	friends. I am John Donaldson, and I am Cyrus Lakdawala, shortly after his passing.
2:18.6	But his widow, Gwen Feldman, put me in touch with a former student of his. So we had the opportunity
2:23.4	to discuss this book and to just hear some amazing stories. I just recorded it with him.
	...

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