In this paper, the author contends that the ability to create a political realm is dependent upon one's state of freedom. She questions what it means to be free and whether assumptions of the definitions of this concept are always good or beneficial. After discussing some of the known theories about freedom, she states that schools are some of the most important sites for the dissemination of a dehumanizing negative freedom. This paper uses Erich Fromm's "Escape from Freedom" to consider the following questions: (1) What is freedom? (2) What is the relevance of Fromm's analysis for education? (3) How can Fromm's notion of freedom contribute to the creation of a space such as Maxine Greene's political realm?