Andrea Mattiello discusses the drawing of an elephant depicted in fol. 144 of the codex Mut. gr. 144, a manuscript compiled in Mystras during the 1440s. This image is one of few surviving autographs by Ciriaco de’ Pizzicolli d’Ancona, as indicated in one of the two Greek inscriptions that accompany the drawing. Mattiello offers insight into Ciriaco’s role in the cultural exchange between Mystras and Italy by placing the image of the elephant within the context of contemporary debates about virtue witnessed by d’Ancona during his interaction with the intellectual milieus both in Mystras and Italy.