As argued in Teaching History for the Common Good, the measure of a democratic society lies in the degree to which its members learn to exercise individual and collective agency in informed, intelligent, and humane ways and to demand the same from national and global institutions. One way in which teaching history can advance democratic aims involves the exploration of the historical roots of democratic dilemmas with particular attention to analyzing the differential agency available to individuals, groups and institutions in responding to such dilemmas. This paper draws on an on-going research project to explore the ways in which personal and aspirational identities support students’ deeper engagement with history. Students’ more nuanced understandings of how the past influenced the present led to interest in and concern for the power citizens have to shape those influences.