Hilary Putnam has been both a forceful champion and penetrating critic of pragmatism. The goal of this paper is to compare and contrast main themes and theses of his philosophy with those associated with pragmatic thought. The task is complicated by the fact that what counts as a pragmatic position is itself not well-defined. To narrow matters down I focus on the writings of the Classic American Pragmatists: Peirce, James, and Dewey, whose work Putnam usually has in mind. The task (...) is further complicated by the fact that Putnam’s own positions have continually changed. Over the years he has often gone from being perhaps the most prominent and insightful proponent of the ideas to be discussed to being the most prominent and trenchant opponent of these same ideas. In what follows I examine selected core features of Putnam’s and the Pragmatists’ positions on: perception, truth, language, and constructivism. I argue that a major difference in their approach to these topics is that the Pragmatists challenge the substantive nature of the realist/antirealist dualisms that underlie the problematics, while Putnam finds it necessary to choose sides. (shrink)