This is a good topic and I've really been on the fence with this one. For me, there doesn't seem to be an easy, clear choice, when looking at either option, for different reasons...
Option #1: A trade to New Orleans centered around Jayson Tatum, likely including a re-signed Terry Rozier, Time Lord (possibly Smart) and a bunch of draft picks. So you roll out:
Anthony Davis / Aaron Baynes
Al Horford / Daniel Theis
Gordon Hayward / Marcus Morris (re-signed)
Jaylen Brown / Semi Ojeleye
Kyrie Irving / Mid Level guy
That starting line probably wins multiple titles if kept together.
* The Bench is defensive and gritty and you can make up their lack of offense by generally having two of your starter on the court at all times
* The idea would be to re-sign Kyrie, win big and then therefore entice Davis to resign long term as well
* Risks: It doesn't work out and Davis can walk
Option #2 is the youth movement:, perhaps keeping Kyrie long term, or not - let's say we do and you use your mid level to simply add another really solid big man like Marc Gasol (after Leonard leaves and Toronto doesn't look so bright any longer)
Baynes / Gasol / Time Lord
Horford / Theis / Yabusele
Hayward / Morris / Ojeleye
Tatum / Brown
Irving / Smart
* You used your mid-level on Gasol
* You have your lower level for a back up veteran PG/SG
* You retain the Sacto pick, The Clippers pick, the Memphis pick and all your Celtics picks
* Depending on how successfully you draft, you could re-stock your bench with cheap young talent, for example:
C - Time Lord
PF - Bruno Fernando (Clipper's pick)
SF- Brandon Clarke or Keldon Johnson (Sacto pick)
SG - Colby White (Celtics pick)
And you STILL have Memphis top 6 protected pick next year and unprotected the year after that...
Both teams could be incredibly great if it all meshed. You'd like to think the AD, Irving team with outstanding glue guys in Horford, Brown, Hayward and the bench could be dominant. But that option #2 team could be just as good and have a much longer window if it meshed. Very difficult off season coming up for Ainge.
His job would be much, much easier if:
1. Irving was a true two player and skilled leader, and
2. Anthony Davis said he'd really like to play in Boston (with Irving...). It still baffles me that he wouldn't want to play in Boston, with the front office, the coaching and all the talent that would be around him for the first time in his career, even after trading for him.