The other thing that people haven't mentioned is that the IT4 would have been a terrible contract negotiation and might have set a bad precedent for JT and JB.
I will say the one thing Ainge did get right was choosing to let IT go when he did. That said, if he really knew that IT was about to fall off a cliff then he wouldn't have been worried much about IT's pending free agency. As we know now, IT after his hip injury was never going to land a contact of any significance. Either way you don't make a trade of this significance because you're afraid of a contract negotiation.
DA was gunning for a title. He wasn't gunning for five years of rookie development. I'm sure he had no idea what Kyrie would become. Obviously, if he did, that would change the analysis but it's hard to fault DA for going out and getting a perennial All-Star.
Again, other teams avoided Kyrie because of concerns about his personality and those teams were proven correct. Ainge overlooked those concerns and we know now that he shouldn't have. It's not 20/20 hindsight to blame someone for ignoring concerns other people had
at the time of the trade.
You do the Kyrie trade 10 times out of 10. At the time, nobody knew how crazy he was and the thought was that he was just a disgruntled star who couldn’t share the spotlight with LeBron, no different than the KG/Marbury separation.
As I remember it, Marbury was also a head case - so I find it a bit odd that he'd be seen as a positive point of comparison. And let's also remember that unlike the chronically middling Timberwolves, Kyrie was unhappy on a perennial championship contender, who had just raised a banner the year before the trade request. And again, it's hard to say "nobody knew how crazy" Kyrie was when there were teams who were concerned enough about those issues that they didn't pursue a trade for him.
But anyway, I 'm not saying this was a horrible trade that was indefensible at the time. I'm saying that there were risks to the trade that were known at the time that Ainge decided to overlook, and in retrospect he shouldn’t have.
That said, I will admit that he was dead-on in his assessment of IT’s future worth. I remember at the time that many wondered if Kyrie was really enough of an upgrade over IT to warrant how much the Cs attached to him. After all, this trade came just a couple of months after IT had what was arguably his best season and placed 5th in the MVP vote. We now know that IT never again would be close to the same player again, and in fact, Ainge chose the perfect time to move on from him.
That said, for many of us the biggest concern was giving up that 2018 pick, and most importantly, whether or not Kyrie was the guy you’d want to cash that in for considering his questionable character. Those concerns were clearly valid.