The first substantive theory of free speech as a secular political right was concocted by two anonymous London journalists, Thomas Gordon and John Trenchard, in their best-selling, endlessly reprinted newspaper column, Cato's Letters (1720–1723). Though its ideals became hugely influential, especially in the American colonies, Trenchard and Gordon's motives and the peculiar biases of their theory remain unexplored. John Locke's theorizing of personal liberty while accepting patriarchy and slavery has been much studied; that of Cato's Letters, a comparably significant text, not at all. Drawing on a wealth of newly discovered materials in British, Caribbean, and American archives, the author explores the telling roles of gender and especially race in early Anglophone ideals of free speech, connecting them to the lived experiences of Gordon, Trenchard, and their shadowy publisher, Elizée Dobrée. The article thus reframes our understanding of one of the most important Anglo-American political works of the eighteenth century, and exemplifies how to approach free speech historically, as both a theory and a practice. Freedom of expression does not simply arise from the lessening of “censorship” and restraint, nor is it ever equally accessible to all. Visibly and invisibly, like every kind of liberty, it always has a particular shape.