Sadly it sounds like he's gotten too far out of hand for too long for a quick and easy solution.

I wonder if he falls into one of the Autistic Spectrum categories?

I've learned with my oldest son that there is no black and white with behavior (not Autistic but they kept trying to attach the ADHD label to him despite doing very well in school). He's never been violent but punishments and repercussions for "screwing around at school" (my term, not theirs), blowing off school/homework, talking back, etc. never enter his head until after the deed has been done and that's when he'd come to the realization that he was wrong. At 11.5 he's markedly better than he was at 8 but he never got away with much without getting punished either.

__________________

1980 300TD-China Blue/Blue MBTex-2nd Owner, 107K (Alt Blau) OBK #15
'06 Chevy Tahoe Z71 (for the wife & 4 kids, current mule) '03 Honda Odyssey (son #1's ride, reluctantly) '99 GMC Suburban (255K+ miles, semi-retired mule) 21' SeaRay Seville (summer escape pod)