The question of how students might concurrently engage in historical empathy as both a cognitive and affective construct remains as a sticking point in the understanding of historical thinking. This study employed three instructional units to place students in situations in which they were likely to engage in historical empathy using both the cognitive and affective domains. Three historical figures from a traditional social studies curriculum were chosen for their specific need to confront a historical paradox. Data include student responses gathered from investigative activities, discussions, historical narratives, metacognitive activities, and researcher notes. Findings indicate that students demonstrate an affective connection to historical figures, and use source evidence and personal experiences to better understand difficult situations. The results further support previous preliminary findings that engagement in historical empathy is not necessarily a mutually exclusive exercise in either cognitive understanding or affective connection, and may be cultivated as a simultaneous combination of both approaches. (Contains 2 tables.)