The stuffy headmaster was far more concerned about the reputation of the school and the “proper” way of doing things than he was in the welfare and growth of the students. In fact, I got the impression that their learning anything was entirely incidental, while conforming to the standards of behavior specified by the school was held to be more important.
On the other hand, Keating screwed up a little by not tempering his lessons about thinking differently, questioning authority, and challenging yourself, with some pointed commentary about personal responsibility. He may have assumed that they’d get the point about Thoreau’s civil disobedience through the fact that Thoreau was willing to go to jail rather than conform, but being adolescents they probably glossed over the part about willingly facing the consequences of your choices, whether those consequences are positive or negative.
I also think that Keating would have given Neil some advice on achieving his dreams while also at least fulfilling part of his father’s requirements. I believe he guessed that Neil was lying, but instead of calling him on it, he chose to accept Neil at his word. He probably thought that Neil would have to learn his lesson about lying by himself. Challenging Neil would have damaged or broken the relationship of trust they’d built and he couldn’t have known that Neil would react so badly to his father’s disapproval.
Keating undoubtedly changed many of the student’s lives for the better, but had to live with a sense of responsibility for Neil’s death. Though the real blame lies almost entirely with Neil and his father, he would have felt guilty about his involvement. Personally, I think Neil would have blown his brains out sooner or later, whether it was over a future conflict with his father, or after 20 years of an unfulfilling life he felt trapped in.
I think that someone with Keating’s attitude would be a great teacher in real life. In fact, I had a physics teacher with a similar approach; I’ve written about him on the boards before. He used to give us scientifically absurd “explanations” with a completely straight face and have us debunk them. His favorite leading question during these sessions was “why?” and his rebuttals ranged from, “I don’t believe you,” to, “You’re full of crap.” He made us tell him why he was the one who was full of crap.
He made us reason and think for ourselves in the face of active challenges from an authority figure. Sure, we knew that he couldn’t be serious, but his role playing was a good way to learn how to deal with that kind of pressure in a safe environment. Besides which, if you can use the things you’ve been taught in order to reason through an explanation of why lightbulbs aren’t “dark suckers” and why a rocket works even in a vacuum, you really and truly understand the concepts and principles behind the facts. That transforms fact memorization and rote formula use into real learning. Learning how to formulate and defend an argument worked with physics and there’s nothing I’ve seen to make me think it would be less effective with arts and humanities.