In this article, we explore the uniqueness of argumentation within the field of history, considering whether historians’ processes in crafting an interpretive argument from inexact evidence might provide insights into processes vital for informed civic engagement and civil dialogue in democratic societies. We discuss the role of argumentation in history, taking both historian (expert) and student (novice) perspectives by considering what historical writing is and how it is produced, taught, and learned. Unlike other research on argumentative historical processes, we examine the role of dispositions that complement skills and enrich collaborations as historians grapple with historical problems together. We examine the role that dispositions and historical thinking skills play as students discuss evidence, plan for argumentative writing, and evaluate their peers’ ideas. We propose that the dispositions and skills involved in historians’ reading, writing, and thinking parallel the critical thinking needed for deliberative and collaborative reasoning about complex social issues. Finally, we explore how instruction and experience with deliberative collaboration within historical problem spaces may prepare students for meaningful civic engagement. We call for increased research on these potential connections.