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I have no answers, thanks for posting in case some others get in this situation.
I do remember this from Educational Psychology class which I've used on students and my own kids countless times:
You reinforce the actions that you acknowledge. Some kids just want attention whether it's bad or good. So far he has gotten attention because he's being a douche.
Take the initiative and compliment him on something. Don't be patronizing, pick something and be honest. You'd be amazed at what barriers will start breaking down.
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