John Dewey - an American philosopher, psychologist, and educational reformer was a leading proponent of American pragmatism. His area of work encompassed philosophy, ethics, and pedagogy , and his thoughts have influenced the education systems of Japan and China. This study, divided in three sections, explores the characteristics of Dewey’s pragmatism and theories of knowledge. The first section introduces his life experiences and considers his ideological characteristics at each stage of his career. The second section introduces the characteristics of pragmatism and concretely clarifies the characteristics of Dewey's pragmatism based on his original works : Democracy and Education (1916) and Reconstruction i n Philosophy (1920). The last section discusses significant aspects of his educational theory, namely his theories of knowledge. Specifically, characteristics at each stage of his theories of knowledge are clarified . This section comprises three parts: stages of Dewey’s epistemological development, overcoming dualism, and schools of thought on the functions of knowledge and methods of knowing.