In this essay, I seek to refine our understanding of historical counterfactuals by classifying them into a new typology. After providing a systematic definition of counterfactuals, I divide them up into five different categories: causal, emotive, temporal, spatial, and manneristic. Within each of these categories, I identify eighteen different types of counterfactuals, which I classify with descriptive names and illustrate with specific examples from recent works of historiography. The different types of counterfactuals vary in numerous ways, but they are all linked by their rhetorical elements. These elements, in turn, help explain the present-day popularity of wondering how history might have been different.