Is the smirk coming from just been coped with self-consciousness? You know bravery isn't the absence of fear, it's really the decision to act in spite of the fear. Maybe the smirk isn't derision, maybe he's terribly self-conscious most of the time. Even if he is comfortable in his own skin.
Sorry the teacher doesn't love him too. I know there's programs that teach kids leadership but I haven't got that far. Do they teach diplomacy?

Youth lives by personality, age lives by calculation. -- Aristotle on a calendar