The Bill of Rights with its famous First Amendment, which forbade Congress from curtailing freedom of speech, had been ratified by 1791, but soon afterwards the Federalist majority enacted the Sedition Act of 1798. The act made it a criminal offense to criticize the Federalist President John Adams and the Federalist dominated Congress or their measures. The basic research question is then: how was it possible for Federalists to argue for the Sedition Act given that the First Amendment was part of the United States Constitution? This basic question was also raised by Republican speakers in the debate when they objected to the proposed new law as a violation of the Constitution. The chapter addresses the question concerning Federalist argumentation by focusing on the speeches in support of the Sedition Act by its leading sponsors, Harrison Gray Otis and Robert Goodloe Harper. It is shown how fallacy theory can again be used in the analysis of arguments presented by leading Federalists, and that many of their arguments were fallacious. It is also suggested that the notion of a covert intention can also be discerned in their argumentation, with different types of evidence supporting such an interpretation.