Freakonomics Radio

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675. Has the New York Times Become a Games Company?

Explore episode May 15, 2026

Where this was said

Human-Made Puzzles vs. AI — and Why Connections Stumps the Machines

At 46:42 · chapter starts 46:40

Dubner asks about AI strategy. Knight's answer is the opposite of most tech executives': NYT Games is doubling down on human-made puzzles. The rationale has two prongs. First, consumers are perceptive — they can sniff out a machine-made game, just as Wordle clones proliferated online without capturing the same feeling. Second, human curation matters at scale: Tracy Bennett's word choices, the discussion of double letters, the cadence of the week's puzzle selections — all of this is invisible but felt. The punchline is Connections: AI companies have told the Times their models still cannot reliably solve it. The misdirects, the human trickery, are too hard to replicate. And there's a brand dimension too: beating a NYT puzzle feels like beating 'a New York Times human,' not just any algorithm.

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