Sometime between 1521 and 1524, more than ten years after Pontano’s death and the fall of the Aragonese dynasty, Sannazaro commissioned a portrait medal that does not correspond to that inscribed in his mentor’s dialog Actius. Girolamo Santacroce (1502-1537), the goldsmith in charge of crafting the medal, represented Sannazaro as a typical humanist wearing a laurel wreath on the recto of this bronze item, while carving a scene from Sannazaro’s masterpiece De partu Virginis on the verso.1 Compared with Pontano’s medal portrait crafted by Adriano Fiorentino, with its elegant profile of the poet in humanistic garb accompanied by the representation of his masterpiece Urania, Sannazaro’s medal was probably meant to be a tribute to, and at the same time a subtle critique of, his adviser’s legacy. Different from the mythological poem announced at the end of Pontano’s Actius, Sannazaro’s quest for poetic excellence had turned away from the mythical heavens of Urania and resulted in a three-book-long Latin poem retelling the mystery of the Virgin birth in polished Virgilian hexameters. In contrast to the astrological explanation of poetic authority implied in Urania, De partu Virginis, as this chapter will illustrate, constructs the author’s persona as undergoing a divinely inspired process of spiritual transformation – a strategy too markedly different from Pontano’s teachings not to constitute a refutation.