My work attempts to uncover a hitherto underexplored area of research that forms a fundamental intersection between Classical Antiquity and the later Mediaeval World. Despite scholarly focus on the use of Aristotle’s Ethika in Byzantine Thought, his equally notable treatises on politics have received less attention. This project seeks to identify the continued relevance of Classical Political Thought in the Aegean World after the “Aristotelian Rediscovery” in Latin West following the Crusades, using the actions and attitudes of a Basileus at the centre of Byzantine Life during the turbulent 14th Century, Ioannes VI Kantakouzenos.