It's either all or nothing for me. If we can't keep Irving and make a reasonable trade for Davis, then I don't think it's worth it to make a desperate attempt for a title run. There are too many question marks. Will Hayward get back to All Star level? How many good years has Horford left? Who's going to run the offense? Is there a possibility to convince Davis to stay?
Sure it worked out great for Toronto, but their situation was a little different. I thought from the start that the Raptors made a great deal. Obviously relying on the backcourt duo Lowry/DeRozan wasn't going to be enough and they didn't have another option than going all-in or watching that team going nowhere.
The Celtics do have a choice. If Irving leaves then that's a huge blow, no other way around it, a top 3 PG in his prime. But in all the acquisitions we didn't lose that many assets (Bradley, Thomas, Crowder, Zizic, Sexton). So if Irving leaves I'm fine with fully trusting our young group (Rozier, Smart, Dozier, Brown, Tatum, Ojeleye, Yabusele, Williams + our picks). Not all of them will make it and neither will those draft picks all work out, but we have a couple of young players who have proven a lot and with some support the ceiling of that core could be very high.
Unfortunately our veterans don't have a lot of trading value, so I'd keep Hayward, Horford and Baynes as mentors. The goal of the team should be to slowly grow, accumulate assets, and hopefully we can add a max free agent in 2021, when Hayward's contract is off the books.
In the case the opportunity is there to give Gordon, Al or Aron a chance to go to a contender we'd of course fulfil that wish. Re-signing Rozier depends on whether we can sign him cheap (less than 8 million a year), otherwise let him walk as he isn't good enough to warrant a big salary. I'd want Theis back, but also only really cheap (in that case trade Yabu for a future second round pick).
The roster for next season would be something like this (nice mix of rookies, young talent and veterans):
PG: Marcus Smart, Brad Wanamaker (or Terry Rozier), #51 Chris Clemons
SG: Jaylen Brown, #22 Dylan Windler, PJ Dozier
SF: Jayson Tatum, Gordon Hayward, Semi Ojeleye
PF: Al Horford, Daniel Theis (or Guerschon Yabusele), #14 Bol Bol
C: Aron Baynes, Robert Williams III, #20 Daniel Gafford
I'd be okay with that.