"Historical empathy" connotes "perspective taking-in-historical-context," or explaining the intentions that motivated behavior within a framework of beliefs, values, and institutions, among other factors, as they existed at some time and in some place, rather than through contemporary norms and perspectives. As a construct, historical empathy is difficult to achieve. This mixed method study explored 38 middle students' experiences of historical empathy in a digital history game. As an interactive medium that provides feedback, video games might be effective tools with which to help learners become better historical thinkers. The goal of the study was to learn more about the relationship between player agency and achieving perspective taking. I hypothesized that three factors might influence players' achievement of historical empathy in the game: prior knowledge, theory of mind (or social understanding), and game play. After operationalizing knowledge using a multiple-choice test and theory of mind using participants' open-ended responses to questions about two ambiguous social scenarios, I sorted students into high and low knowledge and social understanding groups. I operationalized historical empathy using player think-aloud statements and responses to interview questions. The results of two Fisher's exact tests revealed a positive association between prior knowledge and historical empathy and no association between historical empathy and theory of mind. The effect size for the first finding is small, but warrants additional investigation, and the second finding suggests the way theory of mind was operationalized was too broad. Analysis of player statements suggested that, for at least half the participants, the ways in which they engaged in role-play and strategy complicated historical perspective taking, as some evidenced "slippage" between their historical player-character and themselves when reasoning through problems. Thus, role-playing games might encourage "human connection" with the past, while simultaneously making "objective" accounts more difficult. The conclusions suggest that history teachers might use games following direct instruction such that students are prepared to contextualize game events. Further, game designers should anticipate "slips" between players' real-world identities and player-character identities and design constraints that can push back on--without stifling--players' "presentist" assumptions. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]