From your description I don't think he is an ODD-sociopathic kid. Cunning? Definitely! Typically really bright kids can get into trouble before they get the maturation to control themselves. However, because they are really bright, they also tend to figure this out faster then the normal child. Of course, they also can figure out how to manipulate the situation just as fast.
Couple of things do bother me though. You said, "He's been seen by school counselors therepists pediatric doctors etc." Since I doubt that he has seen them all this year - there must have been some past history going on. What have the teachers in other grade levels said? He does seem impulsive. And I don't like the fact that he calls, " himself stupid and idiotic dumb." When he obviously isn't. While he could be saying this for attention, it may also be because he is impulsively doing things before he has a chance to think about it. If he is seeming to become more depressed, or more frustrated with the way things are going- then I would have more concerns.
It is possible he has something like ADHD. Due to his intelligence, the schools would not pick up any academic shortfalls - behavior yes! I have had kids that were not diagnosed until 5th grade or later because the math finally got to hard for them. If he is that sharp, he might not have a problem till algebra. Does his homework take any longer than it should? He probably should be done in 30 min or less.
Anyway, it is important to try and figure this out. If he does have ADHD than the punishments and the way you work with him are different than with a child who is just doing the wrong things. Based on what you have said - I can't tell. The impulsiveness is a definite clue (but that could also be maturation - unless he has always been impulsive). The negative feelings - if they are real - do bother me!
You might want to read a book I recommend a lot on the ADHD forum and that is, "The ADD/ ADhD Answer book." , by Susan Ashley. Another interesting one is, a new book by a UC Berkley honors student with severe ADHD about growing up with ADHD. The book is called - "ADHD and Me, What I learned from lighting fires at the dinner table," by Blake Taylor.
By the way - I have never found that looking deep into someones eyes, or making them look you in the eyes ever helped much. What works is constant discipline so even if they don't show that it is working - they know what will always happen. Of course, if they are having trouble controlling what is happening, then its a different story. Hope this helps. Good Luck!
Let me just say 1 more thing he is very smart has a huge vocabualry loves to read plays "normal" children games I've been told he most likely has a high IQ and can finish a 700 page book in a week loves math and science hates english unless its writting about his own ideas and could care less to learn about art because he feels like his teacher can't teach him anything he doesn't already knkow about it. PHEW!