Understanding historical empathy is a bourgeoning subfield of social studies education research. Students demonstrate historical empathy by analyzing sources 1) to determine historical context, 2) identify perspectives of historical figures, and 3) make affective connections to historical content. Therefore, the purpose of this research is to examine primary sources from educational leaders and organizations during the Progressive Era in American public school education in order to trace the origins of historical empathy as an implicit goal in the social studies curriculum. Our guiding research question is “How does the work of Progressive Era organizations and educational leaders impact how Americans viewed historical empathy?” We purposefully selected documents from Progressive Era organizations and certain leaders whose work formed a strong foundation of social studies education history. We conclude with an examination of the importance of historical empathy today in order to demonstrate the importance of historical empathy as a curricular aim of social studies education.