This study offers a new approach to emotions in writing, further refining our understanding of historiography, the process of writing and attributing emotions, and questions the extent to which we can access medieval kings and their habitus through these narratives. Looking at different conflicts during the reigns of the English kings John and Henry III and different chronicles in comparison, we can identify moral, rhetorical, and political influences, detail nuances and distinctions in descriptions, and highlight the fragile relationship between reality and its description by chroniclers. Although some results are sobering, they paradoxically bring us closer to medieval people, while emphasising the need for caution when approaching these characters, due to the filters we must consider.