Tatum and Brown are the part of the plan that has panned out, and I'm not lamenting them. There just seem to be far fewer avenues to add to that nucleus than there were a few years ago, when we had cap space, potential lottery picks, and more tradable assets.
The part that is tough to breakdown is what were the alternative paths? Because I can't really find forks in the road where DA had a
real opportunity to get a prime player and came up short.
Jrue Holiday - I would hope Danny would never make the deal that Milwaukee made for him. I don't believe he's in the echelon of players you give up the farm for
Anthony Davis - was always, always, always going to the Lakers once LeBron signed there.
Kawhi - wouldn't commit beyond the last year of his contract and SA was asking for JB in return. It's not a slam dunk the Celtics win the championship in 2019 with Kawhi, so would you in retrospect give up Jaylen Brown for one year of Kawhi? I wouldn't. And in FA, it was clear that he had his eyes set on the Clippers
Jimmy Butler - another scenario where he wouldn't commit beyond one year if traded, and I wouldn't trade Jaylen Brown for one year of Butler. In FA, he wanted to go Miami and they S&T for him - Celtics can't compete with that
Kevin Durant - Was never going to sign with Boston, especially because his friend Kyrie drafted him to Brooklyn
Paul George - IIRC, he wouldn't commit beyond one year (and him re-signing in OKC was a nailbiter). Also, in retrospect having seen Playoff P, would he have made a difference these last few years?
Looking at the list of marquee players that have moved teams - Russell Westbrook, Chris Paul, Blake Griffin - feels like rearranging deck chairs on the Titanic. Paul still has some value, but if you thought the Cs cap was bad now, plop his $43 million on there.
Ainge did get two years of Kyrie, who should've been much better but is too much an asshole to realize what it takes to be great, for essentially nothing. He got Horford, who was really, really good for us during his time here. He got Hayward, who would've been great if not for totally fluke injuries. And he replaced Kyrie with Kemba, who you could consider a misstep because of injury risk but when he's played he's been all we could ask of him. Those were four bites at the apple to create a complete, deep, threatening team and unfortunately things haven't lined up yet. I can't hold it against Ainge that Kyrie is a prick and Hayward broke his ankle.
Celtics also got unlucky in the draft by having picks from Sac and Mem during their best recent seasons and during shitty draft years. It happens and it's all luck. But who's to say Romeo doesn't show similar improvement to JB's second year and he's as much of a chit as a player like Landry Shamet?
Now, could we have gotten something more in return Kyrie or Hayward or Horford before they left? Maybe, but the Celtics are also a perennial playoff team. They've been hamstrung by how good they are and didn't have the same options to asset collect as a non-playoff team. It would've been extremely dumb for them to trade some of their best players away to get assets in return when those guys are contributing to deep playoff runs.
I could've missed something, but I'm interested to hear from other posters where Ainge messed up and what he could've done otherwise.