The guy is in a tough spot.
I wish someone would have asked him about the eating of his toe jam. :) It was touched on, and I understand it is not important, but his appearance distracts from his goal. And who in the hell eats the crap between your toes? ( I mean, in public that is, I do so in the privacy of my safe room, duh! )
How in the heck could he have forgotten the belittling of a small kid. Either the OP was in fact making it up/embellishing, or there is no way he forgot, and was covering.
The hypothetical about the software based medical solution; that was a surprising answer to me. In a way, he has invented a religious dogma. He seems to have an answer to everything that comes up, in the same way religions also have an answer for dinosaurs and aliens.
Just pick a damn movie and pick a damn book for Christ's sake! :)
This one just killed me:
When a company says, "We want to merge with competitor XYZ,
since we are too small to compete in this market, and by the way
the merged company will become the biggest in the field," we
need to respond, "We won't let you merge. However, we just split
your biggest competitor into 5 pieces; maybe now you will find
it easier to compete."
His inability to adapt his position hurts him in the long run. When making comments about textbooks, it was clear to me, that the preferable solution would be to use a free textbook over a non free textbook. I can get behind that. However, when the quality of the non free textbook is abysmal, you must go with the non free version. We are talking about one's eduction, or health, or life saving scenario, their future in general.
Giving up a little in the beginning to position yourself to be able to make sure that what you gave up in the beginning never happens again, is the adaptation he lacks, which hurts his end game.
Compromise does not seem to be in his vocabulary, yet I suspect he would be so much further along had he learned about it. He may walk into a meeting with major leaders of other countries to get them to look into free software deployment on a scale of millions. That sets the tone to be able to one day implement his idealistic end game. That meeting would have no negotiation to it, it would be his way, or no way, in which case, Microsoft just made all the money, and he took a step backwards for the sake of being stubborn.