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these two geniuses face off in a game of chess. which will win?

Shikamaru. Kisuke is more manipulaty then chess smart.

I don't recall Urahara ever being good at this kind of thing. Whereas Shikamaru is shown to be an expert in the manga itself.

yah but the thing is that kisuke is a analytical master so you shouldn't just count him out

And Shikamaru is an analytical master (his feats in that area are better than Urahara as well) as well, PLUS he has skill in strategy games.

Urahara is an analytical master at science.

Scientist vs tactician in chess, tactician wins.