This article addresses two understudied topics in history and identity research: How individuals assign and take up positions while they explain controversial history and the personal identity negotiation they experience in this process. The study uses positioning analysis to examine adolescents’ negotiation of history and identity through their historical explanations. Positioning analysis examines the cluster of social rights and duties, which people assume and assign to others to make sense of society and themselves. This study conducts an in-depth analysis of the historical narratives of two 16-year-old Mexican and Spanish adolescents about the 16th century Hispanic Conquest of Mexico. The analysis focuses on the positions that participants establish to explain history and how they use these positions to configure their own identities. The outcomes show three common types of positioning used by participants to explain the Conquest, which oscillate between the legitimization and rejection of colonialism. Findings also suggest that positions allow adolescents to mediate tensions between cultural affiliation and historical explanation, as well as creating their own versions of collective and personal identities. Finally, the implications of these findings for historical understanding and the analysis of the psychological impact of colonialism are discussed. (PsycINFO Database Record (c) 2019 APA, all rights reserved)