Was George Orwell an Optimist?
The Freedom Rider - Art Blakey and the Jazz Messengers
The Brief and Frightening Reign of Phil - George Saunders
Funky Disco wrote:
...does it really just come down to which war he's more interested in?
I think that's the key. If he's interested in the subject, he's far more likely to enjoy the game. Note that there are two other games available in the same family: Commands & Colors: Ancients and Commands & Colors: Napoleonics. Pick the one that matches his interests best.