This mixed-methods study investigated how secondary social studies educators mediate their own and their students' emotions while engaging in pedagogical reasoning and teaching about difficult content within a highly charged sociopolitical landscape. This research was informed by sociocultural theory, Shulman's (1987) model of pedagogical reasoning and action, and Zembylas's (2007a) work on emotional knowledge. This study consisted of a quantitative phase and a follow-up qualitative phase. For the first phase, 96 teachers from 27 states plus Puerto Rico and Washington DC completed an anonymous survey focused on teachers' pedagogical decisions for teaching difficult historical events and the challenges and risks associated with teaching such events. Participants were from public, private, and charter schools, and worked in rural, suburban, and urban school districts. This survey allowed for the organization of teacher participants into a typology of emotional engagement. Purposeful sampling led to the selection of six teachers for the follow-up qualitative phase of the study. These six teachers had varying demographics and emotional engagement practices. This phase consisted of interviews and stimulated recall tasks focused on exploring the dispositions, thoughts, decisions, and practices of teachers in different emotional engagement categories. Crystallization of the quantitative and qualitative data sources revealed various risk calculation heuristics that teachers engage in at the levels of: pedagogical risk, professional risk, contextual risk, and emotional risk. Additionally, findings highlighted how emotional disclosure serves as a pedagogical tool for facilitating classroom discourses centered around difficult content and the emotions such content elicits. These findings have important implications for how to research and teach about difficult content, leading to new opportunities for educational research, social studies education, and teacher education. [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.]