This article will attempt to offer the first literary analysis of the Dialogue with a Persian of Manuel II Palaiologos. Despite its rich theological and literary material, this work has largely been neglected by scholars. However, the Dialogue deserves to be studied for its literary merit and not merely as a historical source. After a brief overview of the contents and background of the Dialogue, this study will focus on its literary features, especially on the vivid character portrayal of the Ottomans and the emperor himself.