Researchers have found that when young people participate in discussions of controversial political issues, they often become more politically engaged and informed (Hess, 2009). Nonetheless, some educators avoid fostering such discussions because they can become heated and distract from academic learning (Hess, 2002). Presidential elections, including the highly publicized debates, provide substantial material for discussions of major national and international issues, but no published research has examined how educators can leverage these events to generate productive civic learning experiences. In this article, we analyze data collected in seven high school classrooms during the 2012 presidential election to examine the challenges and opportunities associated with generating substantive, dynamic discussions of presidential debates. Our findings indicate that students enjoyed learning about candidates' different perspectives and that certain strategies were especially helpful for fostering substantive discussions: (a) scaffolding students' preparation for discussion; (b) providing opportunities for students to address open-ended questions; (c) redirecting students' engagement in competitive, interpersonal dynamics to learning about public issues; and (d) countering students' partisan tendencies. We discuss implications for practice and research and present a conceptual framework for generating dynamic, substantive democratic discussions.