This article gives a historical-philosophical overview of three generations of pragmatist thinking centered around the question of democracy. It serves as an introduction and contextualization to the papers that develop a third generation pragmatic point of view in the remainder of the special issue. The perspective is from one American-trained philosopher of education who has studied and written widely in pragmatism and European social theory. The article has sections on three generations generally described and with primary influences of John Dewey, Richard Rorty, and Bruno Latour. In each generation, other important philosophic contributions discussed come from C. S. Peirce and William James, Hilary Putnam, Donna Haraway, and Isabelle Stengers as well as relevant commentators. The first two, Dewey and Rorty, contribute to a sub-theme of democracy in their writings that the third, Latour, continues in politics in a section elaboration. The introduction sets forth a generational theme and an international setting for pragmatism. The conclusion summarizes the article's key ideas and points to a need in education for a democratic future.