Board Thread:Episode Discussion/@comment-34633327-20180120015359/@comment-26397825-20180121235809

Ruby is not Dorothy; this question was asked at a panel and we were told Dorothy is another character. So that throws your whole thing with "Ruby = LRRH + Dorothy which means Qrow = Munin + Scarecrow" out the window right off the bat.

In fact, given the situation Oscar is likely Dorothy at the moment. He's a young teen who lived on a farm with his aunt and setting out on a perilous journey to combat an evil witch. In Return to Oz, Dorothy speaks to Ozma (the rightful ruler of Oz currently deposed from her throne, just as Ozpin was once the ruler of Vale and gave it up, and is currently 'deposed' from his throne at Beacon) through a mirror, just like the scene Oscar first meets Ozpin in.

The parrallel/reversals between them is that while Dorothy didn't want to fight, was uninterested in the world of Oz itself, and did everything just so she could go home, including needing to be tricked into fighting the witch in some versions (since her way home was on her feet the entire time and she could have left at any moment if they'd simply told her), Oscar chose (with some prodding) to go on the journey, to learn how to fight, and to face the challenges and work towards saving Remnant from the Wicked Witch (Salem).

And given the theming with the Headmasters al representing a character from Oz, the Scarecrow is not Qrow. Qrow wasn't even a teacher at Beacon like Glynda was, he taught at Signal. The Scarecrow is most likely the Shade Headmaster, since RT has been very sure to stick to their guns on the theming and allusions for 'quartets' like the Academy Headmasters.