No one knows what will happen. Danny might want to keep all three because they currently fill most of the guard needs. Jaylen and Gerald can fill the big tall shooting guard role if needed. Rozier backs up the first three guys who are proven NBA machines.
If Danny drafts and keeps a phenom stud guard, that would definitely cause some friction and redundancy.
Danny has one more window to add a free agent all-star or high quality role player, then the CBA allows teams to pay whatever it takes for retaining. There's too much basketball time left to speculate. So many different things could happen. I'm thinking about Portland.
Having Isaiah, Avery, and Marcus on the same roster for the rest of their careers would not be a bad move by Danny. It is contingent on Marcus honing his Chauncey Billups skills.
Bradley and Thomas together is kind of short at times, so that is where Marcus Smart comes in.
I think Danny hits for one more big free agent and/or trade, then resigns those guys.
This is all subject to change which means it's better to just watch and appreciate their efforts, and when their contracts come up, expect they will be resigned. Expect the best outcome. Olynyk is the next big decision. I guess Amir, Jonas, Tyler and others also have immediate unstable future security as Celtics.
I don't understand the need for excessive speculation. Do you want the players on edge always thinking it never ends? I think Jae said that, that it never ends. My rant is over, however.