TODO: strip out now-defunct formatting
(Note: I’m using this to play around with RemoteWikiLink ing on a large scale, partly just to see how ugly it is. And, looking it over, it’s pretty ugly. But it sure beats typing (or even pasting) a lot of URLs, and I like the richness of all those links. Ignore all the BlaH: prefixes; I’ve tried to make the sentences work, mostly, if you read the links as text.)
Most important UgP:PhilosophyOfEducation (see also: WiP:Philosophy_of_education) has been UgP:DemocraticPhilosophyOfEducation. This is not accidental; the ruling classes under whatever governmental structure have always been able to take care of their own; while UgP:Education was always vital to them, it was never a problem—and thus never acquired a WiP:philosophy. But, with the growth of democratic and pre-democratic philosophical forms (e.g., WiP:The_Enlightenment , WiP:Protestantism) that were proposing to turn the whole shebang over to the grizzled mass of humanity (which, it was recognized, was, to smudge WiP:Hobbes a bit, poor, nasty, brutish, and short), it was quickly realized that something would have to be done about said mass.
WiP:Jefferson was a good one for recognzing that a democracy is only as good as its citizens, but he is hardly alone; Plato and Rousseau (WiP:Philosophy_of_education#Plato, WiP:Philosophy_of_education#Rousseau) both wrestled with it to varying degrees, and of course the great prophet of democratic education is UgP:JohnDewey.
What is interesting about this great tradition is, of course, that education itself is virtually never democratic. That is to say, it may, (particularly in its Deweyan form) be thoroughly interested in democracy, wholly committed to it, and entirely about it, but at the end of the day (take that, GooGle:plain+english+campaign) education at the primary and, usually, the secondary levels (the only levels which are incorporated in true WiP:Public_education) is almost always undemocratic—i.e., the participants (students) are mostly without any formal power or democratic voice, and indeed do not even have a clearly defined or protected right to exit the process. Thus, if public education is the foundation of a democratic society, than democratic society is founded precisely on the negation of democracy. (UgP:Zizek would be all up in this motha.)
What’s more surprising to me is that hardly any democratic philosophy of education actually acknolwedges this fact, let alone copes with it. I doubt Dewey could even conceive it. Sizer gives it a shallow nod with his assertion that there are limits to how much schooling a government is entitled to force on its students. Rousseau acknowledged outright that education is always founded on relations of force, but did not provide a systematic justification for this position.
UgP:Arendt , in her discussion of the fate of authority in the seminale essay, “What is Authority” (Between Past and Future), offers this explanation:

The most significant symptom of the crisis (in authority), indicating its depth and seroiusness, is that it has spread to such prepolitical areas as child-rearing and education, where authority in the widest sense has always been accepted as a natural necessity, obviously required as much by natural needs, the helplessness of the child, as by political necessity, the continuity of an established civilization which can be assured only if those who are newcomers by birth are guided through a pre-established world into which they are born as strangers.”

(Interestingly, this, if coupled to UgP:Weil ’s critique of the concept of WiP:Human_rights , would open the way for a coherent response to the UgP:ProblemOfTheRightToTeach. But I digress. (“Oh, like that’s unusual for you”—UgP:SportsNight))
For Arendt, of course, it is, far from being problematic, necessary that education be kept apart from such political ideas as democracy. She views any attempt to change education systematically as a form of philosophical tyranny comparable to Plato’s scheme, a sort of illicit politics by other means. (cf. UgP:AxiomOfPerfectMethod) The solution she proposes is a radical division between primary and secondary education and collegiate education, or even between all three and graduate education. Her entirely unreasonable assumption is that, while philosophical interventions in education are problematically political, education as it stands is not politically problematic. (This split is, amusingly, also advocated by WiP:Rorty , of all people) Of course, such a division of labor is obviously untenable in a society where only some go on to college, and in any case would be highly suspect, as it could only devolve into some embracing some existing and implicit philosophical tyranny and rejecting any attempt at making our politico-philosophical universe at all consistent.
We can also find something vaguely like a recognition of the problem of democracy and education in certain radical educational philosophies. One might argue, for example, that UgP:Freire ’s elimination of the teacher-student dichotomy solves it. Of course, said elimination is highly suspect—Freire offers far too little account of how one can remove or purify power relations in real-life teaching scenarios. Also, Freire’s critique of education is grounded entirely in a quasi-WiP:Marxist realism regarding human nature (i.e., Freire believes that there is such a thing!) and not in a truly democratic philosophy of education.
I recently stumbled across a rather delightful little article (“Can There be a Liberal Philosophy of Education in a Democratic Society?”, by Bowles and Gintis) that comes a bit closer, also Marxist, but taking the form of a critique of liberal democratic educational philosophy as such. There’s more market analogies than I like, but their basic point-that it is hard to imagine how an undemocratic education (an education of “learners”) effectively prepares people to function as powerful citizens (“choosers”) in a democracy-is reasonably well argued. They offer relatively little in the way of a solution, however:

Our critique of the instrumental conception of action bears the unavoidable implication that a viable theory of education in a democratic society requirs the rejection of the fundamental liberal partition of individuals into learners and choosers and its replacement by a theory which takes acount of the manner in which class relationships, the state, the family, and other structures regulate our own individual and collective projects to shape who we are.

In other words, “We’re Marxists!” Well, viva la revolution, baby, but that doesn’t actually tell me anything I can use.
So far, I can think of only at most two ways of dealing with the problem.
1. Setting aside the question of early childhood, which is probably an insoluble problem anyway, make all schools completely democratic. One body, one vote. Which I’m all for.
2. Make the tension between the democratic aims and aspirations of public education and its gerontocratic reality an essential part of the educational process. This would involve highlighting as part of the curriculum all the ways in which kids are not free in our society. In other words, it would teach democracy by a via negativa, a practical tutorial in what democracy isn’t—i.e., school.
Of course, these could be integrated to varying degrees, but if we wanted to get serious about two, we would actually want to make schools as unfree as possible—in other words, assume that tyranny is the best stimulus towards strong democracy. This has many, many parallels in UgP:FrankHerbert , though I’m not sure what that gets us.