What Jennifer Shahade thinks about LLMs
American chess player, poker player and writer; US Women's Chess Champion in 2002 and 2004. Author of Chess Bitch, Play Like a Girl! and Thinking Sideways. Writes a newsletter on chess, poker and decision-making and co-hosts a chess YouTube channel with Fabiano Caruana.
Jennifer Shahade did not write this page.
We collected these quotes from things they published elsewhere, and every quote links to where it was said. They have no account here and have not endorsed this site. Quotes are word for word; the short line under each one is our own restatement, not their wording. Their own site. Is this you? Claim it or ask us to remove it. Or tell us what is wrong here.
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3 dated positions, 2026, in their own words. Our reading of what Jennifer Shahade has said — not written or endorsed by them.
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Their wordsLLMs aren't trying to give you a random result, but a likely result, and their training data contains lots of sevens. So that's what you'll get. Again and again. Unless you prompt it not to.
↗See the Sideways Movejenshahade.substack.com 1st of 3 in this piece
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Their wordsWhat feels like a random, organic process may be leading us down a narrow path of cool sounding numbers and ideas.
↗See the Sideways Movejenshahade.substack.com 2nd of 3 in this piece
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Their wordsAs we are surrounded more and more with LLM generated text, images and ideas, the value of divergence will go up and up.
↗See the Sideways Movejenshahade.substack.com 3rd of 3 in this piece