You have to think the Cartel crew believes they are getting the waiver.
They already announced he has a lawyer working it and his family has money. If he really could have graduated in May and come in as a grad transfer I don't think he takes this risk of the waiver unless his lawyer thinks its a wrap. Kid has been riding pine for two years now, he has to be foaming at the mouth to get going. I don't think they are taking a shot in the dark with the waiver when he could have gone the grad transfer route. This leads me to believe he'll be playing this year. Enrolling now and participating in spring isn't worth risking not being able to play until 2020 unless they know they're good.