Board Thread:Speculation House/@comment-24189217-20140926023352/@comment-24891101-20140926024302

He knows that RWBY has tangled with long odds and come out ahead: the Nevermore, the Paladin. And he's sending them with a trusted friend of his. And it was really the best decision: Oobleck can return them to Beacon if they're really in trouble, whereas if they went off on their own, as they would had Ozpin not intervened, then they'd not be supervised.

And despite what Ironwood thinks, Ozpin seems more willing to gamble the lives of his students, regardless of the above.