Walter Benjamin wrote about pedagogy from the start of his writing life to its close. He was also an activist in the youth movement in Germany. This essay explores the importance of childhood, play, toys and education to his wider body of work--including his interests in photography, literary form, language acquisition and use, modern art. The opening up of these areas in relation to questions of pedagogy enables the organisation of his thought in relation to two complexes: "colonial" and "communist" pedagogy. What these mean, what determines them and how they further Benjamin's project of emancipation, which begins with youth, is scrutinised here.