oddest............................. NOT OLDEST
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has got to be John Brunner's "The Squares of the City" (1965, publisher unknown since I don't have the book any more). A political novel (?!) based on a game between Steinitz and Chigorin in 1892. I read it many years ago and got rid of the book because:
1. I couldn't find the corresponding game (pre-internet)
1 ... so I couldn't follow along on a chessboard
2. kinda cheesy, who cares about South American politics (sorrry, S.A.)
2 ... the main character "was" the king's knight, who gets taken in the game on move 35 but still is around at the end of the book (as opposed to most of the other characters who get killed or jailed). Anybody else read this? or something stranger?