Thanks for your replies. I'm still stumped by what motivates him to be around these kids. He's not lacking in self-esteem, he's a confident kid generally. I've seen him ignore other kids who try to be friendly. He's always been very single-minded about certain things...wondering if this is a case of once a friend, always a friend kind of misguided loyalty.

I need to be aware of my own tendency to worry as I suffered bullying in school, that's why I'm being careful that this isn't about me, and trying to take cues from him and getting him to think whether it's acceptable behaviour