Dio Chrysostom’s “Trojan Oration,” which aims to disprove Homer by a close analysis of his text, is a complicated work. Contextualized in Dio’s corpus, it is a sophistic exercise. Its scope and skill, however, make it a successful example of multiple genres. One such genre, it is claimed, is that of a pro-Roman Panegyric. His favorable language towards Rome and imaginative description of its “true” origin has generally been taken as a matter-of-fact, if skillful, praise of Roman order. Read in light of the text as a whole, however, this is clearly incorrect. Instead, it ought to be read as satirical and ironic, just as the rest of the text is. To read it otherwise undermines the critical purpose of the text as a whole and misunderstands the purpose of the whole critique. This can be more clearly proven by examining a few instances in the oration when he makes references specifically to Virgil’s Aeneid, but does so in a way that both undermines and contradicts his work. These specific references have not been identified before, but also show Dio’s willingness to interact directly with Latin literature on the Homeric tradition. Whereas the Roman panegyric has sometimes been made even to dominate the purpose of the text, a proper contextualizing within the true satirical purpose of the oration makes sense of Dio’s language and helps better understand its whole structure.