I'm not sure why you think a teacher would put his or her students into prison by telling them the content of freedom. My puzzlement is this: Isn't the question of whether or not I am free or in prison an objective fact about me and my life? It may well be that a teacher can lead a student to recognize (perhaps for the very first time) just how constrained and unfree the student really is. But that is not the same as actually creating the constraints. In fact, I am inclined to think that the more we know about the limits on our freedom, the better equipped we will be to moderate or eliminate our limitations. Perhaps still the most important philosopher of education, especially in regard to the kind of question you are asking, is John Dewey.

Philosophy can offer a little hope--but only to those who manage to listen or read philosophy, and those are probably not the ones who need the help the most. As with so many things, the only real hope for education is that people will become more willing to make the sacrifices necessary to make improvements to what we are doing now. In society, that eventually becomes a matter of our willingness to spend money on education--through taxes for public education, though tuition for private education, to pay for higher salaries and better working conditions, so the best and brightest will find teaching an attractive option, and to diminish class sizes to make sure that students get the kinds of access they need to more personalized instruction. As long as our society (and others) are bent on trying to make as much money as possible, while spending as little as possible on education (or worse, spending so much on other things that--even if we wanted to--we wouldn't have an adequate amount left for...