In the twentieth century, the antinomy of freedom and coercion served as the dominant paradigm for understanding issues of crime and punishment. Roscoe Pound in Criminal Justice in America (1930) and Herbert Packer in The Limits of the Criminal Sanction (1968) described a tension between the values of individual liberty and general security to explain the problems with the justice system and the public's disagreements over their solution. Historians of twentieth-century criminal law have also adopted this framework to explain causation and change. This essay argues that an antinomic perspective of criminal justice history, while useful, has obscured important historical questions. A focus on social changes, such as the transformations that the automobile brought about in the commission of crimes and police practices, instead of on contrasting values, offers a different account of how proceduralism became inextricably tied to notions of American freedom in the twentieth century. This approach also historicizes the “paradigm of antinomies” and shows how people in the past, like Pound and Packer, mobilized dualistic thinking, which shaped a criminal legal culture based on an antagonism—both real and perceived—between citizens and law enforcement.