“Trade for AD and let Kyrie walk” should be labeled as the franchise suicide option.
My (mostly emotional) preference is for Kyrie to go play for a fanbase that will enjoy his antics more and won't care so much about seeing good team basketball. The Knicks or Lakers would be perfect.
I don't want to trade for AD with just a year left on his deal when our franchise is in such a volatile position. Very good chance of that blowing up on us. Just look at Toronto -- as great as things have gone with them and Kawhi this year, if they lose Game 7 on Sunday, or even if they lose to the Bucks in the ECF, Kawhi could very easily decide to leave for LA or wherever.
I know that many folks here don't like the idea of "build around Jay & Jay" because they see that as aiming for the middle. However, I think that perspective overlooks the fact that if the team maintains cap flexibility, doesn't sign anybody to any crazy contracts, and continues to stockpile assets, there will still be plenty of options for improving the team.
The goal is to win a title. To do that the team needs to have at least one if not multiple top tier guys to build around. You also need those guys, and the supporting cast around them, to fit well so that they can thrive together. On top of that, you need to be able to sustain multiple years of contention, because even historically talented teams fail to win titles given a single season (see 2011 Heat).
With all of that in mind, I just don't have confidence that going all-in for Kyrie and AD makes sense when we know that both of those guys have a history of being mercurial and, to put it kindly, failing to step up to the plate as far as leadership and taking responsibility for the team are concerned. That's not even noting their significant injury histories.
The Kyrie and AD plan made a lot more sense to me when I believed the Celts were building toward that from a place where the foundation of the franchise was exceedingly stable. It still is from the standpoint of the front office and the coach. I don't feel that way anymore about the infrastructure on the roster and the culture of the team at the ground floor level.
So to me it makes sense to move forward with our young guys, try to keep Horford and Smart around (Hayward isn't going anywhere) for leadership and stability, and see whether or not Jay & Jay can make the leap. If they can't, the team can lie in wait for the next opportunity to add a potential MVP talent.
If the Celtics end up trading for AD and retaining Kyrie, I will be able to mentally get on board with the plan just because of the sheer talent. When you can pair an All-NBA, perennial All-Star with a potential MVP caliber talent, the reasons for doing so hardly need to be articulated.
My concerns will be (1) whether the chemistry and the fit is likely to be there given what I would perceive as a void of leadership in that pairing and (2) that the pairing won't actually result in very many opportunities to win a title because AD may leave after a year or they may never be fully healthy at the same time.
I truly, truly do not want an emotional sequel to the dispiriting, depressing 2018-2019 Celtics season.