If he likes baseball that much, perhaps a carefully chosen adult who also happened to be very successful academically to work on his baseball with him (and chat about how high school and college actually work -- I think you need to maintain a certain GPA to even play)? If he's worried about "cool" then yes, you will get pushback on anyone who's not considered cool. I think that some colleges even have baseball camps for kids his age -- maybe you could find something like that where academic success is a prerequisite?
Also, with my son, we have had far more success with very very smart male teachers. He doesn't bond the same with female teachers and if his teachers aren't perceived as smart by him (and there is a little jockeying on his part to "test" them)... things just don't go as well. I think if I had had a very smart and demanding female teacher...a go getter, who really pushed me, I would have responded better. They were too easy on me. Always. Too nurturing. They expected so little...
I think that age is very tough though because it's normal to stop looking to parents and start looking to peers. We will be there soon enough and I'm already dreading it.
Apparently, MS isn't only hard on the Middle Schooler -- it's hard on us parents too. I wish we could just skip over it altogether. Hopefully there are some people out there with some good advice!
