On the verge of his adolescence, two events steered Theodore’s life in new directions: the appointment of a court tutor and his betrothal to a foreign princess who likewise was an early adolescent. Theodore writes that he had just “come of age” and was “running the course of his twelfth year” (1233) when his parents made the decision to select his tutor.1 He refers to him as his “pedagogue” without ever describing his duties or giving us his name. The manuscript heading of his devastating Satire of the Tutor ascribes to him the title of baioulos or “preceptor,” and this is significant. The position of baioulos, or grand (megas) baioulos, was given from at least the fifth century to a court educator in charge of the upbringing of an imperial prince. According to the Satire, the “pedagogue” wore a tall, red hat made of wool when he entered the palace on a feast day, which made him resemble a crocodile and a mouse emerging from its hole. The spoof shows that he held a ranked court position, because hats had become an attribute of holding an imperial title in Byzantium by the twelfth century. In the fourteenth century, the megas baioulos ranked seventeenth or eighteenth among more than sixty court titles. In other words, the tutor belonged to the middle-to-upper segment of the court hierarchy.2