Board Thread:General Discussion/@comment-2600:387:5:805:0:0:0:C3-20191231004957/@comment-27745396-20200107081812

The headmasters seem to follow the themes of Dorothy's friends in Wizard of Oz: Cowardly Lion, Heartless Tinman and Brainless Scarecrow. Expect instead of seeing them to gain their lost things back, we have been shown these characters' fall from the grace. Lionheart was told to be a brave Huntsman, but all we saw was a coward and Ironwood is slowly becoming a heartless military leader who care more about the endgoal instead of the people (Even after E9, I still think he's going to snap).

So by that logic, Theodore is the most likely going to be a someone who has been seen as wise or smart person (a scholar perhaps?) who will start or has already started doing really stupid choices. Or perhaps he is developing a some sort memory effecting disease like Alzheimer.

Appearance wise, he obviously will end up having something that screams the Scarecrow (Lionheart's name and tail, Ironwoods name and robotic parts). It's a bit harder than in case of the two other ones, but perhaps him having thin but long limbs could be a good enough hint. That and straw like hair.