Although modern systems of mass education are typically defined in their opposition to violence, it has been argued that it is only through an insistent and critical focus upon violence that radical thought can be sustained. This article seeks to take up this challenge in relation to Walter Benjamin's lesser known writings on education. Benjamin retained throughout his life a deep suspicion about academic institutions and about the pedagogic, social and economic violence implicated in the idea of cultural transmission. He nonetheless remained committed to the possibility of another kind of revolutionary potential inherent to true education and, when he comes to speak of this in his "Critique of Violence," it is remarkable that he describes it as manifesting an "educative violence." This article argues that Benjamin's philosophy works toward a critique of educative violence that results in a distinction between a "first" and "second" kind of education and asks whether destruction might have a positive role to play within pedagogical theories in contrast to current valorisations of creativity and productivity.