The thesis addresses the way in which Philostratos, writing in the early third century C.E., fashions a new version of the Trojan War in the central part of his dialogue, the Heroikos. The study presents a thorough analysis of the dialog’s sources and their use, and of the parallels with other literary and non-literary texts from the Imperial period. It also examines the ways in which this text addresses a set of broader interrelated questions such as the status and nature of the Homeric poems and conceptions of truth, lies and fiction. As a dialogue about events from the distant past known primarily through canonical poems, the Heroikos combines fictional creation with a form of criticism that goes beyond the domain of the literary to address questions that were key to the Second Sophistic. The aim the research is, therefore, to throw light on the text from Philostratos’ culture, identifying rhetorical concepts and practices as well as broader intellectual habits which were widespread in the Imperial period