The process of engaging in historical empathy holds the potential for significant curricular and dispositional benefits for students in history classrooms. In order to realize these benefits, classroom teachers must be able to integrate historical empathy into their existing planning and teaching; a process that would benefit from empirical examination. This single subject case study examined the pedagogical reasoning process of an experienced classroom teacher who integrated historical empathy into an existing instructional unit designed to foster student knowledge of social control as an enduring historical understanding. The findings of this study suggest that experienced teachers may only be able to partially anticipate the unique pedagogical needs integrating historical empathy requires, and that a holistic examination of pedagogical reasoning during all phases of planning and teaching may be most suitable for the task.