As is well known, Jews, chess, and philosophy go together. The world champion Emanuel Lasker was a philosopher and mathematician by training.
Most famously chess is used as a setting for the greatest of all philosophical novels, Lewis Carroll's Through the Looking Glass and what Alice Found there. In "folk" philosophy, chess is often used as a philosophical metaphor for life's absurd rule-following, or for the belief that we are just pawns in the hand of fate or the gods (or God), as in FitzGerald's translation of Omar Khayyam's poetry:
But helpless pieces in the game He plays(It should be noted that chess isn't mentioned in the original Persian, but added by the translator.)
Upon this chequer-board of Nights and Days
He hither and thither moves, and checks ... and slays
Then one by one, back in the Closet lays
There is an actual book about chess' uses in philosophy: meaning, here, professional philosophers' use of it, not the folk-philosophy above. For philosophers, chess is not a matter of human's lack of free will, but usually an illustration of rule-following, of a logical self-contained world, or artificial intelligence. Wittgenstein, in particular, used chess as a metaphor quite often; Rousseau confesses to have met the great players of the day, Philidor included, 'without making the least improvement in the game' -- a confession as damning, to a chess player, as his better-known confessions on other matters.
Prof. Hale, the author, certainly written an interesting work for both chess players and philosophers.