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Perpetual Chess Podcast

EP 481- IM Greg Shahade: Inside His Incredible Jeopardy Run

Perpetual Chess Podcast

Perpetual Chess LLC

Leisure, Sports, Hobbies

4.8 • 706 Ratings

🗓️ 5 May 2026

⏱️ 77 minutes

🧾️ Download transcript

Summary

IM Greg Shahade has long been well known in the chess world as a three-time national scholastic champion and the founder of the Pro Chess League and the US Chess School. Recently, however, he reached a much broader audience with an impressive run on the syndicated trivia show Jeopardy!. Greg amassed over $75,000 in winnings, dethroning 31-time champion Jamie Ding along the way. He joined me after what he described as “the craziest week of his life” to discuss: The approach to adult learning that helped him go from trivia novice to Jeopardy! champion in just a few years Behind-the-scenes insights from the recording process, plus his reflections on his controversial on-stage mannerisms How his background in chess (and poker) shaped his strategy and decision-making under pressure There isn’t a ton of chess discussion in this episode, but Greg’s approach to learning and performance has clear applications across many domains. 00:00 Introduction  Check out our sponsors, Chessiverse.com , and you can use code Perpetual30 to save 30% on premium feature and/or IM John Bartholomew’s Complete Scandinavian Course.  Chessiverse.com 03:00- Greg Shahade joins the show, we begin by discussing adult learning and Greg’s late start to trivia.  Mentioned: Learned League  Thinking Sideways by Jennifer Shahade  Ducksters  07:43 Building Knowledge Structures 10:03 The Role of Intense Study 12:54 Flashcards and Review Techniques 15:43 Betting Strategies on Jeopardy 18:45 Reflections on the Jeopardy Experience You can review questions Greg faced here: https://www.j-archive.com/showseason.php?season=42 25:00-  Patreon mailbag question- Why does Greg know so little about current events? What is his approach to daily double hunting? 30:44 Daily Double Strategies and Insights 36:57 Patreon mailbag question- Why is Greg so expressive when playing Jeopardy? 42:16 Physicality and Focus in Jeopardy 49:25 Behind the Scenes of Jeopardy 52:40 Facing the Champion: Mental Strategies 55:11 The Weight of Anticipation: Media and Public Perception 57:02 Navigating Fame: Love, Hate, and Public Reaction 59:50 Preparing for the Tournament of Champions 01:03:51 Chess and Jeopardy: Cross-Disciplinary Insights 01:07:20 Reflections on Study Techniques and Memory 01:11:20 Final Thoughts: The Game and Its Emotional Toll Thanks to Greg for joining me at a busy time. Follow him here: Instagram: https://www.instagram.com/gregshahade/?hl=en X:  https://x.com/GregShahade Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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1:34.2

Hello everyone and welcome back to perpetual chess.

1:36.3

We've got a really fun interview coming your way with my old friend,

1:39.7

International Chess Master, Greg Shahadi, who has been in the news a ton for crushing it on the trivia

1:45.3

show, Jeopardy. We'll get you to that interview in one minute. Just wanted to mention a few things

1:49.6

that we forgot to cover in the interview number one. If you haven't seen Greg's performance where he

1:54.2

wins over $75,000, you can actually watch Jeopardy on Hulu or Disney Plus. You might be able to find the episodes on YouTube. So I think a lot of you will have seen it, but if you haven't, you can find them. It's a fun show to watch generally, and it's a lot of fun when you have a rooting interest. So you can check that out. Another thing to note, there's a handful of times during this interview where a specific question comes up from Greg's run. And in those cases,

2:18.7

for those of you watching on YouTube, I was able to find the questions on the website, Jay Archive,

2:23.1

Jeopardy Archive, and show them in the video. So if that's important to you, you might want to

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