Two early essays from the year 1765 set the scene for Herder’s lifelong engagement with the topic of patriotism. Both are focused on the question of modern patriotism. Reading them side-by-side one is nevertheless struck by their contrasting tenor. An earlier unfinished essay, How Philosophy Can Become More Universal and Useful for the Benefit of the People, is highly critical of modern society and politics, while Do We Still Have the Public and Fatherland of the Ancients celebrates modern developments, including luxury and modern freedom. In an effort to explain these differences, this chapter argues that these essays represent an important intersection between two kinds of debates on Rousseau’s moral and political thought in German-speaking countries. Herder entered the debate as a self-avowed ‘Rousseauian’, while he soon also became aware of economic and political debates that were originally shaped by Montesquieu. In these debates, Rousseau had come to be seen as a defender of austere democratic republicanism modelled on early Greek societies. This was not the Rousseau Herder wished to associate himself with. The second essay is thus replete with implicit references to Abbt, Hume and Hamann. The same orientation was shared by the local elites in Riga.