Growing up in an era when protest at national political conventions is carefully contained in "free-speech zones" (often physically removed from the site of the official conventions), students today may have a difficult time conceptualizing the tumultuous scene that was the 1968 Democratic National Convention (DNC) in Chicago. Fueled by the consensus-shattering backdrop of the Vietnam War, the upheaval of a civil rights movement turned violent, the assassinations and abdications of national leaders both beloved and despised, and the cultural chasm opened by a rising generation of questioning youth, the chaos and unrest of that historic confrontation open up a unique opportunity for twenty-first-century youth to review fundamental issues of democracy that continue to shape America's political culture. A perennial issue confronting democracies is: When does free speech become punishable for "intent to incite a riot"? This article offers a blueprint for addressing this issue through a class reenactment of the Chicago 8 Trial that resulted from the turmoil of the 1968 Democratic Convention. By introducing students to legal issues relating to free speech, the re-enactment offers "a riveting exploration of a pivotal historical moment that students and teachers alike will not soon forget." (Contains 10 resources.)