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To begin with we must ask whether Dewey was a Deweyan. This could be done by revisiting the contexts of how one reads Dewey, how one talks to Dewey’s philosophy, and how education, liberty and disposition converge in a conversation with Dewey’s work. As the complexity of a Deweyan argument unfolds, it becomes clear that Dewey cannot be anything but Deweyan because this compels everyone to recognize one fundamental measure by which we can communicate: that of a social way of living marked by radical diversity, and therefore conditioned by the fact that there cannot be one solid idea which excludes everything else. Here Dewey is presented in his various contexts and influences, including his relationship with Hegelian philosophy, Emersonian transcendentalism, Darwin’s method of scientific experimentation, and pragmatists like William James and Charles Saunders Peirce. Dewey’s life experiences, notably his deep bond with his first wife Alice Chipman, their work in the Laboratory School, and the mark that the Chicago experience left on his thinking, provide significant backdrops to this discussion. In this, as in subsequent chapters, the historic contexts of American politics and philosophy feature heavily. This discussion takes stock of what does a diverse and plural society mean to us today, at a time that remains challenged by the politics of class, race, gender and sexuality. Dewey’s work has a profound bearing on our understanding of these challenges. Thus to read and talk Dewey is to engage with a conversation with Dewey the philosopher who poses an array of questions, ranging from the way we feel (aesthetics), behave (ethics), think (logic), live as a community (politics), and how we learn (education). In this conversation with Dewey one finds an approach where, rather than simply describe his work or present an intellectual biography, readers are presented with an authorial dialogue with Dewey’s philosophy. Right from the start, it is argued that Dewey must not be trapped by narrow categories, such as that of a progressive educationalist or as some father figure for liberal schooling. Rather, Dewey’s work is presented as a critical junction marked by the quandary of schooling and culture, and where learning is also positioned beyond the boundaries of educational institutions. This presents the possibility for education to be free and yet rigorous enough to help us engage with forms of knowledge by which we negotiate and understand the world.