This paper explores Erich Fromm's contribution to Deweyan democratic education by referring to his psychoanalytic interpretation of John Dewey's pragmatic theory. First, it employs the work by Gert Biesta to secure a space between critical pedagogy and Deweyan democratic education, from which Fromm's theory can be discussed. Furthermore, it argues that Biesta's perspective offers a valuable theoretical ground to extend the emancipatory potential of Deweyan democratic education, while avoiding some pitfalls of critical pedagogy. Subsequently, the paper contrasts Marcuse's and Fromm's views on Dewey to show how Fromm's understanding of Dewey was more effective than that of Marcuse for developing the potential of Dewey's philosophy. Next, the paper clarifies key similarities and differences between Fromm's psychoanalysis and Dewey's pragmatism, as it is applicable specifically to emancipatory education. Finally, the paper argues that despite the differences between these two thinkers, Fromm's theory further radicalizes Deweyan democratic education by adding new elements to the list of preconditions on the role of the emancipatory teacher.