Before AI could annihilate grandmasters, Psion Chess was already humbling humans back in 1985. Available for DOS and Macintosh, this game wasn’t flashy, but it didn’t need to be. It was a smug little program that could outthink you in five moves and then quietly pretend it hadn’t. The board was simple, the pieces lifeless, and yet you’d find yourself muttering “just one more game” at 2 a.m. Psion Chess didn’t just teach chess—it taught humility. Losing to a monochrome screen never felt so intellectually bruising.
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