The Quest for the Golden Fleece, an ancient Greek legend related in various literary sources, includes examples of many leadership and teamwork challenges that face modern companies. Using this mythical story about Jason and Medea, two of the most famous figures from Greek literature, this case study addresses how strong personalities, different leadership styles, and the power of teamwork can accomplish seemingly impossible goals. In particular, this case study examines the leadership dilemmas that arise when working in a team of experts and near equals as well as the pitfalls of such partnerships, particularly when a romantic relationship develops between team members. The case also addresses how team dynamics change over time and the challenges that teams face in incorporating new members to an already high-functioning team. Finally, this case compares and assesses the leadership styles of the myth’s two major characters, Jason and Medea, who are not only partners in the quest for the Golden Fleece but also lovers. Their personal relationship complicates the needs of each character and their interactions with the rest of the Argonauts. Finally, this case considers factors of gender and ethnicity in how these figures have been treated by other characters and by audiences over time.