This book focuses on a selection of Machiavelli’s literary pieces, among which are the Mandragola, Belfagor, the Vita di Castruccio, the Epistola, and the Pastorale. As research into literary motif, it raises, across five essays, new evidence on Machiavelli’s sources and suggestions as to where he drew from them (including the works of Livy, Virgil, and Boccaccio). Of the two other essays included, one intimates the way in which Shakespeare seems to have reappropriated Machiavelli’s Mandragola in The Two Gentlemen of Verona, in addition to Chaucer’s Knight’s Tale. The other is concerned with Mantegna’s Minerva Overcoming the Vices and proposes interpretative contexts for several of the painting’s iconographic details. This book will be of interest not only to those specialising in Machiavellian and Shakesperean literature, and the artwork of Mantegna, but also to those curious about how and why pre-Christian works have been drawn upon by subsequent Christian authors.