Lets say hypothetically any of these players were on the table for Ainge if the deal was right. Based on contract/years left/and package for them which deal did Danny drop the ball on? Personally I feel all three were possibilities for us if Danny wanted them:
Boogie Cousins...
Jimmy Butler...
Paul George...
Fultz...
In every case the return was, I think, shockingly small - meaning that Ainge was simply not willing to give much up for any of those players; ironically, the return for Fultz was impressive (provided you agree with Danny that the top players in the draft were on the same plane. We shall see).
The case against Cousins is easy to make, and the indications were that Boston wanted no part of his antics.
That leaves Butler and George.
They didn't get Horford in order to contend in 3-5 years, which would correspond to Jaylen Brown's timeline. In other words, acquiring a star who can create and make shots is a priority now. So signing Butler, George, or Hayward (or Griffin, though he's now off the table) is logical.
If George was unwilling to commit to an extension, there was no point in continuing the conversation.
To me the no brainer answer is JB, perennial allstar, top 15 player in the NBA, on what some may consider a 'bargain contract' by today's NBA standard. Considering Jrue Holiday just got $25 mil a year, taking on Butler for a lottery pick was easily the biggest miss for Ainge.
I also feel he is the best fit in a Stevens system, adding him to a 53 win team (and also possibly Hayward) while Cleveland is in a clear downward spiral to me is the biggest miss in Ainge's tenure this far.
I agree that he'd be a good fit on the Celtics. I can't say that I have a plausible theory why the Celtics' Brass would prefer Hayward. Throwing his coach under the bus in public didn't help, I'd guess.
I also feel his presence on the team increases the chances Hayward signs here.
Perhaps. But there's a question also of playing time for Brown and even Tatum; and Zach Lowe reports that Crowder was the sticking point in the Butler negotiation.