A couple of things, and you can take me at my word or dismiss me as making it all up, which would be weird.
Bailey and his family were very upset that Pruitt was fired. As his dad said when the rumors were running rampant, "we signed with Tennessee because of Jeremy Pruitt." They were assured by Fulmer that Pruitt was going to be fine multiple times - we know how that story ended. They were going to enter the portal at that time, but figured he should stay in school and complete the Spring semester before making a decision. I think that was smart, and what guys like Crouch and Henry should have done.
As
@Bassmaster_Vol posted above, Bailey has not been totally consistent this spring. There were times he was running with the 3rd string behind Hooker and Maurer. He showed out in the Spring game, absolutely, but I don't think it was totally representative of how he performed throughout Spring ball or where he stands in the pecking order. The VQ guys have been adamant that if the season started today, Hooker would be the starter. You can tell me they're wrong on this, but I don't think they are.
There's a reason why Heupel was so desperate to bring Milton in - someone far from a polished product or a sure thing. Simply put, he doesn't like what he has at the position. And I believe he is preparing for one or two of them to leave on their own.