I second warrrreagl's call for some kind of evaluation - honestly, it sounds like the kid might have some kind of clinical disorder of social/emotional development. Given his mother's strange affect, or lack of it, chances are he may have a genetic predisposition to affective disorders, or he may be suffering abnormal development due to abnormal social cueing from his mom. And if he's been in a Montessori setting up till now, they may have either been able to adapt to his behavior, or they may have just missed it and chalked it up to different learning styles. Could be that the challenge of a new setting and new expectations has triggered some kind of deficit that might not have emerged before. It might help to get in touch with one of his former instructors and find out what kind of issues they had or didn't have with him, and what they did that worked for him.
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"If ten million people believe a foolish thing, it is still a foolish thing."
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