“A horrid-looking wretch he is, sooty and scoundrelly in aspect, a cross between the nutmeg dealer, the horse swapper, and the night man,” declared a Stephen Douglas–leaning newspaper of Abraham Lincoln during the presidential race of 1860. 

For the 1968 DNC in Chicago, Esquire sent Terry Southern, Jean Genet, and William S. Burroughs to cover it. A “hard-hitting little press team,” Southern wrote, that, later joined by Allen Ginsberg, “had one hell of a time actually getting admitted to the hall, despite proper credentials. Burroughs and I, of course, are veritable paragons of fashion and decorum—but Ginsberg and Genet, it must be admitted, are pretty weird-looking guys.”

For publishing an editorial critical of John Adams’ Federalist administration in 1798, Vermont congressman Matthew Lyon became the first U.S. citizen tried under the Sedition Act. He was fined $1,000 and sentenced to four months in federal jail. He ran his reelection campaign from prison, winning by a two-to-one margin. He resumed his post upon release.