After Hegel the Philosophy of Freedom becomes increasingly illiberal. Whereas for Hegel the nation-state was a middle ground between the extreme Left and Right, Marx, Nietzsche and Heidegger embraced revolutionary visions of a future transformation of mankind in which the state vanishes. Hegel extolled classical Greece for its balance between democracy, Platonic philosophy and high culture. Nietzsche and Heidegger instead embraced the pre-Socratic view of existence as war – more suited to their revolutionary stances. They still agreed that historicism could provide a unified account of life rivaling Plato in scope. That belief was shattered by the Fact/Value distinction, which restored Rousseau’s dualism between nature and freedom and made it a permanent chasm. Belief in a comprehensive theory of history was further discredited by totalitarian movements like Marxism-Leninism and National Socialism which used it to deify tyranny. Academically, the Philosophy of Freedom fragmented into Critical Theory, Postmodernism and Hermeneutics. Politically, radicals like Lenin, Fanon, Shariati and Dugin adapted it to their extremist purposes. Given its arguably dangerous political implications, I conclude by asking: Was the Philosophy of Freedom a mistaken path that should never have been taken? Or might it still contribute to liberal education today?