This paper presents a Natural Language Processing approach for the in-depth study of ancient Greek literature. Specifically, our project mines the largest data collection of ancient Greek literature to extract descriptive words and their contextual collocations. We then present the Python libraries developed to perform sentiment analysis with a focus on words about gender, race, religion, ethnicity, and other distinguishable characteristics and how they were used by Greek authors. Finally, we showcase some initial findings as a proof of concept.