This article is a part of an ongoing dissertation work with a purpose of describe and develop knowledge about teaching responded to children’s play (Pramling et al, 2019). What happens to children's “free” play1 when teaching is established? The question stems from the idea “children are free” in relation to play (Huizinga, 1949). The Convention on the Rights of the Child (UN, 1989) becomes interesting to weave into the discussion, since the CRC are enabling children to feel free. In order to understand why teaching at a preschool can be criticized an understanding of what teaching implicates as well what play implicates in relation to the concept of free must be made. I turn to Arendt (1961) and Berlin (1969) who have different views on the concept of free. What happens if we place free next to teaching?