This article examines Joseph Bryennios’ Forty-Nine Chapters, a text that has been hitherto explored mostly for the information on social practices in late Byzantium. The analysis of the text's rhetorical techniques indicates that Bryennios departed significantly from other contemporary collections of kephalaia which relied on the inherited wisdom of gnomologia. I argue that the pervasiveness of figurative language and vivid analogies in the Forty-Nine Chapters shaped his specific didacticism and unveiled the author's acquaintance with the technique of rhetorical amplification.