User blog comment:BenRG/The Chosen One/@comment-14843841-20130825130458

I don't really believe Ozpin had any knowledge of Ruby before the failed bobbery of the Dust shop. From where I see it, Glynda was hunting Romeo and his henchmen that night and stumbled on her while fulfiling her mission. Something is happening under the sheets and the Hunters are working to either find out what it is or prevent it from happening. It must be something really big for them to need all that dust(I also doubt that was the first dust shop that was robbed, or the last).

Ruby was just in the right place in the right time. About him knowing alot about Ruby, I don't think that's he case either. Ozpin is the headmaster of an advanced level Combat Academy, so it is natural he has acess to some degree of information about students of lower level, students from which he'd later select to enroll in his own academy. During the interview, he asks where Ruby learned to use Crescent Rose too. If he knew so much about Ruby, he'd already know just where and who tought her. He looks surprised when Ruby tells him about her uncle.