Following the first European voyages of exploration to the New World, several Ottoman authors debated whether Alexander the Great may have already known of the American continent in classical antiquity. By exploring the contours of this previously unstudied intra-Ottoman debate, the present article challenges the prevailing scholarly view that sixteenth-century Ottoman writings about the Americas were at best frivolous and at worst incoherent. Instead, these texts engaged with many of the same questions provoked by the discoveries in contemporary Europe, while at the same time intersecting with the most profound and contested concerns of Ottoman statecraft.