This essay examines the relationship among some key elements of Charles Sanders Peirce's general theory of scientific inquiry (such as final causality, real possibility, methodological convergence, abductive reasoning, hypothesis formation, and diagrammatic idealization) and some prominent issues discussed in the current philosophy of history, especially those pertaining to the role of generalizations in historical explanation. The claim is that, appropriately construed, Peirce's recommendations with respect to rational inquiry in general can provide a reasonable basis for formulating a productive critical method for a responsible philosophy of history. The essay further seeks to reduce the tension between Peirce's interest in epistemic convergence and the arguments that champion the value of historical distance and perspectival pluralism. On the account offered, the kind of methodological convergence envisioned by Peirce need not conflict necessarily with a responsibly construed historical pluralism. On the other hand, the critical perspective of an epistemically disciplined philosophical inquiry may prove indispensable in weeding out wishful but unrealistic ideological perspectives from the writing of history. Hence, the resulting proposal envisions the critique of historical imagination as one potentially viable modality for the pragmatist philosophy of history.