For the first time, Walter Benjamin's critical comments on educator and philosopher Rudolf Steiner are examined in depth. In particular, Benjamin detected protofascist themes within Steiner's seemingly progressive notion of child-centered, arts-based, developmentally appropriate early childhood education. But this does not mean that Benjamin completely rejected Steiner's work as mere ideology. Instead, we can find the subtle trace of Steiner's influence in Benjamin's own reflections on childhood. Here Tyson E. Lewis calls for a dialectical approach modeled by Benjamin that allows us to critically interrogate Steiner's progressive education for protofascist tendencies, while also redeeming various insights into the lives of children. This dialectical approach to understanding the complex relationship between progressive education and fascism is now more urgent than ever before.