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[–] TheRedArmy 4 points (+4|-0) Edited

If you can, for The Art of War, read the ones that also include commentary from various Chinese scholars and such. That's the one I had, and their insight is interesting.

The Prince (in keeping with your theme)

1984 (a favorite)

Harrington on Hold 'Em (Poker's fun)

The Gulag Archipelago (On my list)