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This article foregrounds the crucial importance of El Inca Garcilaso de la Vega's reading of the Classical tradition in the construction of the historiographic, philosophical, and epistemological categories deployed in his work as translator and chronicler. The first section examines El Inca's stylistic and conceptual appropriation of Leone Ebreo's Dialoghi d'amore, and the application of Ebreo's Neoplatonic syncretism to a metaphysical identification between Cuzco and ancient Rome. The second section situates Garcilaso's own fascination with Julius Caesar within a literary and literal genealogy of soldiers/writers that begins with the Roman and finishes with El Inca. By using the Classics as a starting point to understand Garcilaso's negotiation of Greco-Roman, Jewish, Renaissance, Andean, Christian, and broader transatlantic categories, this essay demonstrates how El Inca both propounded and sought to embody a mestizaje far more complex than the Spanish/Indigenous duality through which he is often understood.