History is the study of what happened—the paths, both chosen and unchosen, taken by people in the past. But what about what didn’t happen—the paths not taken, the choices not made, the outcomes that never came to be? Historians refer to this topic of debate as alternate history or counterfactual history. The study of counterfactual history—of what might have happened, had some factor been different—is highly controversial among professional historians. Some scholars argue for a careful embrace of counterfactual analysis as a way to shed light on the causalities and contingencies of actual history, whereas others argue that it is fundamentally an exercise in fiction-making, more properly the domain of novelists than of scholars of the past. In this first-year seminar, we will engage with counterfactual histories, both scholarly and literary, that engage three historical questions that attract a lot of counterfactual attention, including: what if Europe had not “conquered” the Americas after 1492? What if the Confederacy had won the Civil War? and what if the Nazis had prevailed in World War II? We will also try our hand at creating our own counterfactual histories, persuasive narratives about what might have happened based on a deep understanding of what actually did happen. In doing so, we will work towards a deeper understanding of how we can know the past.