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Utilizing Homeric and historic narratives, Dio Chrysostom exemplifies the creative relationship between Classical Greek culture and Second Sophistic oratory in his “Second Discourse on Kingship.” Such concern for Greek history and culture has been identified as the product of the first three hundred years of the Common Era, in which the ascendancy of the Roman Empire united diverse ethnic groups while simultaneously eclipsing former Greek imperial power. Far from mere conservative expressions of nostalgia for lost Greek glory, however, oratorical projects like that of Dio demonstrate active attempts to manipulate popularly revered cultural narratives in the service of individual, contemporary aims, in this case Dio’s pedagogical agenda in describing the just king. Dio thus utilizes widely known Homeric and historical narratives in order to substantiate his own ideas in relation to these narratives. His work thereby demonstrates how Classical literature remains relevant in the Second Sophistic not only as a source of nostalgia for a lost past, but also as a practical means to advance one’s own ideas within a widely accepted framework.