This article focuses on face-threatening attacks on the Madison Administration during the War of 1812. The discussion is framed by the First Amendment to the United States Constitution, with the language of the Amendment protecting freedom of speech, and also by the Sedition Act of 1798, which, if it had been made permanent, would have seriously curtailed freedom of speech. The War of 1812 was intensely unpopular among members of the Federalist Party, and their newspapers did not shy away from criticising it. This article investigates writings published in the Boston Gazette and the Connecticut Mirror during the war. It is shown that the criticism took different forms, ranging from accusing President Madison of “untruths” to painting a picture of what was claimed to be the unmitigated hopelessness of his position, both nationally and internationally, and that the criticism also included harsh personal attacks on his character and motives. It is suggested that some of the attacks may be characterised as exhibiting aggravated impoliteness. The article also considers President Madison’s attitude in the face of the attacks.