The central thesis of the book is that concepts of the theory of informal fallacies and of applied pragmatics can enhance our understanding of the nature of political argumentation in early American politics. In Chap. 1 central analytic concepts are explained and the four case studies, each bearing on freedom of expression, are presented. The first concerns the first debate in June 1789 on whether a bill of rights should be debated in an expeditious fashion. There was considerable opposition, and the authors substantiate the view that arguments of the opposition involved covert intentions and deceptiveness and that they were fallacious. The second case study examines the final debate on the Sedition Act in the House of Representatives in July 1798 and it is argued that the main sponsors of the proposed act engaged in fallacious argumentation. The third case study concerns the enactment of the Logan Act of 1799, and its main sponsor is likewise argued to have engaged in fallacies. The fourth case study analyzes argumentation of two newspapers in the run-up to the elections in New York in 1800, whose outcome was important because it led to the demise of the repression of the Sedition Act period.