I have dealt with this and my feeling is that you are not going to get anywhere. Even if you somehow get him to cave, he is going to make sure that he is proven right, and look for all the negatives. When he starts crying in school it will be, "See, I told you he was too immature and you wouldn't listen." (rather than trying to help solve the problem) KWIM? We had the option of switching schools and getting into a better environment, which solved our problem, but that's not an option for everyone, so you may have to just make the best of it.
