In this article I will challenge a received orthodoxy in the philosophy of social science by showing that Collingwood was right in insisting that reenactment is epistemically central for historical explanations of individual agency. Situating Collingwood within the context of the debate between simulation theory and what has come to be called “theory theory” in contemporary philosophy of mind and psychology, I will develop two systematic arguments that attempt to show the essential importance of reenactment for our understanding of rational agency. I will furthermore show that Gadamer’s influential critique of the reenactment model distinguishes insufficiently between the interpretation of certain types of texts and the explanation of individual actions. In providing an account of individual agency, we are committed to a realistic understanding of our ordinary scheme of actionexplanations and have thus to recognize the centrality of reenactment. Nevertheless, Collingwood’s emphasis on reenactment is certainly one-sided. I will demonstrate its limitations even for accounting for individual agency, and show how it has to be supplemented by various theoretical considerations, by analyzing the different explanatory strategies that Christopher Browning and Daniel Goldhagen use to explain the behavior of the ordinary men in Reserve Battalion 101 during World War II.