I agree that some of the absolute whiffs with later picks like Yabu, Hunter, Zizic did hurt us and there were a reasonable amount of rotation players he should have gotten with at least one of those picks. I am a bit surprised you would rather have Warren than Smart at this point especially given Warren has basically been out the last year and a half. He is obviously a better offensive player, but we probably need perimeter defense more than we do additional scoring with our teams the last 3-4 years (brown, tatum, rozier, kemba, hayward, morris all wanting too many shots already.
What exactly was the proposed George trade? Also do we have confidence he would have stayed here and not done the same thing he did to OKC? Seems similar to Leonard in that he really wanted to eventually end up in LA.
I wouldn't necessarily rather have Warren, was just pointing out that he has been a similar level of player to Smart so acting like Smart was a homerun can't miss draft pick isn't really accurate, especially with Randle and LaVine both in the lottery after him.
I think the George trade that was rumored to be on the table was Crowder, Smart, and a 1st (the one that became R. Williams) - some reports had an additional 1st or two being involved, but reportedly not the BKN one we used in the Irving trade or the LA/SAC pick (maybe Memphis and another Boston, as an example). The trade was being discussed in June 2017 so it was before free agency opened. As I recall, Indiana wanted the trade to be done, but Ainge didn't want to pull the trigger until after free agency started because he thought he could create more cap room by signing a player first and then making the trade. When Ainge delayed, they moved on and traded him to OKC for Oladipo and the pick that was used for Sabonis.
I said it then and I still maintain, Ainge should have just pulled the trigger and acquired George and then figured out how to sign Hayward after the fact. As it was, Boston had to drop some salary so had to trade Bradley for Morris. I'm sure Boston could have just moved some salary without taking back Morris and still made the room to acquire Hayward. And then still could have potentially acquired Irving with Bradley instead of Crowder. I absolutely believe that even as good as Lebron was, the C's with a starting 5 of Irving, Hayward, George, Tatum, and Horford with Rozier, Brown, Baynes, Theis, etc. on the bench would have gotten by the Cavs that first season. Wouldn't have beaten the Warriors that year, but certainly would have been set up very nicely if George re-upped in the summer 2018. Even if Irving didn't stick around the following year, with George, Hayward, Tatum, Brown, Horford, and probably Rozier, the long term outlook would have been a lot better.
Not acquiring George was really the beginning of the end of the Ainge era. It was indicative of his indecision that he had the last couple of years. He just couldn't pull the trigger time and time again, and the one time he did he picked the absolute worst player to pull the trigger on (both in personality and on the court).