The article proposes the critical analyses of the P. Mehring conception of philosophical pedagogy founded on the German idealism and Humboldt’s philosophy of education. Transformations of the philosophical pedagogy are considering on the background of organizing changes in the education in the industrial and post-industrial contexts with regard to its meaning, logics and causes. The advantages of the interdisciplinary approach are proving on the problem field of the philosophical pedagogy in times of its rising and falls.The restoration of philosophical pedagogy of the early and developed industrialism is proposing with its idealistic and institutional paradigm (Humboldt-Hegel-Spranger) and the alternative one – the critical anti-institutionalism(Nietzsche -Adorno-Foucault), The heuristic metaphor of the invention of freedom shows on the political engagement of philosophical pedagogy what has both the negative and positive aspects. Some political pathologies of the state in the early post-industrial societies need pedagogical treating. That is why the revival perspective of philosophical pedagogy is inquiring. For this case some actual ideas of W. von Humboldt and its transformations are used to show the risks and dangerous of educational reforms in the post-industrial contexts.The Kantian and Hegelian transformations are researching with the aim to show different tendencies of the development of education in philosophical reflections of pedagogical issues with political consequences regarding as possible paradigmatic changes which can exist as complementary ones. The coherence of political and pedagogical ideas can exist in different constellations pursuing different purposes. The pedagogical construct of freedom as autonomy was often used in the political programs and political decisions, but the political reason is also an important factor for the transformations of contemporary educational systems and practices. The pedagogical construct of freedom foresees the autonomy of educational institutions and independency of individual which cal be lost by his transforming to a Wikipedia-citizen.