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While not being an expert in psychology I would initially say that this kid has a fear of failure. Maybe during his younger years, his mother or father put too much on him and things went badly for him or something to that effect. It's almost as if he feels by knowing he's going to fail, he doesn't dissapoint someone by giving them high expectations.
You say he's bright, hows his homework level? Does he get good marks on his assignments?
Injuring himself is a definite cry for help. I'd say its a way of hiding or deflecting emotional pain from his past, or maybe even his present. Hows his homelife? Wheres the father figure?
Crying at confrontations with his mother on his failings.....yet a bland excuse when you ask it. I'd say he's desperately seeking approval and praise from the mother. He may have never had any but without his prior montessori history, its hard to tell. This may also have something to do with your perceptions of the mother. If her baggage is being taken out on the child then he's getting the double whammy of both his and hers, not fair at all to him. This could explain almost all of his issues.
If you're truly concerned with the childs welfare then maybe you should seriously consider asking the advice of a professional. Start taking detailed notes of your daily activities, conversations, and interaction with him. Present these to the professional you talk to.
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"no amount of force can control a free man, a man whose mind is free. No, not the rack, not fission bombs, not anything. You cannot conquer a free man; the most you can do is kill him."
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