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In 1776, the English historian Edward Gibbon published the first volumes of his History of the Decline and Fall of the Roman Empire. Gibbon’s paradigm of “decline and fall” maintained that the ancient world had swiftly and dramatically crumbled into a millennium of medieval darkness, torn asunder by what Gibbon labeled “barbarism and religion.” This temporal map did much to shape the emergent discipline of Classics, formalizing distinctions that, over the course of the nineteenth and twentieth centuries, would privilege a supposedly canonical Greco-Roman antiquity over other cultures and periods of the past. Yet Gibbon, whose History extended all the way to the capture of Constantinople by the Ottomans in 1453, hardly considered himself merely an ancient historian. Rather, as he claimed, his Decline and Fall would do nothing less than “connect the ancient and modern history of the world.” This lecture explores just what Gibbon meant by linking the ancient and the modern. In doing so, it examines how early modern European scholars in the centuries before Gibbon defined such categories as antiquity and modernity. When had modernity begun, and which portions of antiquity should this nascent modernity replicate or imitate? Which eras counted as truly ancient? And what purposes did a millennium-long “middle” period between ancient Rome and contemporary Europe serve? Retracing the history of these historical concepts—and their many paradoxes—promises to shed new light on our own approaches to the ancient world and its temporal boundaries.