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This book offers a multidisciplinary contribution at the intersection of legal history, classical studies, and AI ethics. Prompted by renewed interest in sycophancy and its unsettling relevance to Artificial Intelligence, the work examines the deep historical roots of the term and the phenomenon, combined with the widespread hostility toward sycophants in ancient Athens. By reconstructing this phenomenon and drawing parallels with today's generative AI, the study fills a gap in both historical and technological literature. It provides analytical tools to assess the epistemic and ethical risks posed by AI systems, particularly in relation to manipulation, rhetorical conformity, and the erosion of critical thought.