This chapter is the first of two “foundations” that form the second part of the book. Starting with an analysis of the analogies drawn between Donald Trump and Roman emperors across the mediascape of 2016, it introduces the temporal and political relationship between the Roman and American republics, via the work of Hannah Arendt and Ian Baucom. It then moves backwards through American history, from the twenty-first to the eighteenth centuries, bringing in a wide range of American writers: Ursula Le Guin, John Williams, Upton Sinclair, Nathaniel Hawthorne, Henry James, Louisa McCord, Mercy Otis Warren, and several others. Keeping the Roman analogy at the heart of its discussions, this chapter ultimately demonstrates the ways in which writers generate networks of coeval connection between ancient past and modern present in order to variously uphold and break down the seemingly contingent political, social, and racial logics of American empire.