hesperiidae
Yeah, so it is! I guess I ran into the same weirdness as ShamelessC, since when I first Ctrl-F:ed the PDF, hit 1/11 was on page 11. Now that I try my damndest to reproduce it, I get 12 hits and the first is that one on page 10.
The Culture is (in this story) pretty much only bound by their own constraints. They chose Gurgeh for the role, since he had enough skill and talent to actually be able to accomplish the Culture's (or the SC's, winkwink) objectives without having the whole thing being taken over by an AI.
The Culture worked very much like the PoG this thread is about: it minimised potential loss and considered the constraints it had to get the best possible outcome.
The Culture is mostly constrained by only ethical rules, which, admittedly, can get flexible, especially with regards to the SC. The practical restrictions, like it being easier to send one capable human than to conquer a small galaxy, are in my mind lesser in comparison.
As such, I think they got the most out of the operation, just by being confident in their assessment of a single human who played games good. And there's absolutely no reason to believe that the overminds that guide the Culture can't model human behaviour down to the smallest variable, especially considering how augmented humans are in the Culture.
I'm also 100% onboard the idea that all the drones could outplay Gurgeh in a blink in any game, intuition be damned.
Really, Culture is a great setting for discussing a lot of interesting philosophical questions and topics.
Use of Weapons is more than a decent intro, but I'd still personally recommend The Player of Games since it isn't as deep and heavy in comparison, and the narrative structure is simpler.
Of course, YMMV, but I started with TPoG, and reading UoW right after it was absolutely fantastic. I guess my biggest concern with recommending UoW as the starter would be that it might diminish TPoG, which I'm fond of, but I don't know if it actually would, since they're connected pretty much only bound by the setting.