First off, I was not trying to say he will be judged solely on these trades. Even if these moves fail he will always get credit for the Garnett teams and the fast turnaround in the last few years. My point was these trades are big enough and controversial enough that they will have a significant impact on his eventual legacy. You may not want to see it, but Ainge bucked conventional wisdom with these trades to a degree that he never has before (at least not on moves of this significance). And I know you disagree. But the idea that trading the #5 pick in a draft that was seen as two-star deep for a hall of fame guard (i.e. the Ray Allen trade), or that blowing up a team that was clearly too old to contend was "miles more bold and risky" is just not true. If people want to love these trades that is their right, but you have to respect the fact that Ainge bucked conventional wisdom with both these moves and that puts him in a position to look particularly bad if they fail.
I know people are piling on a bit here, but I get your basic point: if there's an extremely strong consensus, it's usually there for a reason, and it's generally hubristic (a word?) to think you can beat that consensus consistently.
That said, I think the Fultz trade is the main one deserving of analysis. The debate with Kyrie was whether Ainge paid 70 cents on the dollar, 100 cents, or 120. I don't think that the consensus is super-off from what the Celtics paid--the main disagreement is how good Kyrie will be in the Celtics' system. If he turns into a top 10 player, it was a fair trade regardless of how the Brooklyn pick turns out. If he doesn't, it's an overpay. If the Nets are way better than projected, I think we give the Celtics a bit of credit for projecting the East, and chalk the trade up as a slight win, even if Kyrie is "only" a top 15/20 type guy.
So, the Fultz trade. There are two ways to look at it. The way kaz is looking at it is as a bet on the Celtics' internal player evaluation. Seen that way, and with Danny's meh track record of pre-draft talent evaluation (not great, not awful), it's not an awesome bet, I think kaz is correct to be skeptical.
However, I don't think the Celtics are betting on player evaluation so much as they're betting on the price of star trades. The typical price of a disgruntled star with 1-2 years left is a top 3-5 pick plus some assorted parts to make the deal work (win-now vets, salary matching, late picks, etc).
It doesn't seem to matter a ton if that top 5 pick is an already drafted player, a pick with a good chance at being top 5ish, or a pick that's already slotted into a certain spot. The only requirement if it's an already drafted player is that he still has to have some new-car shine (think Jayson Tatum post summer league, not Dragan Bender). Even Oladipo was a #2 overall, and I think that affected Indiana more than it should have.
So given that the Celtics think they have an attractive organization (Kyrie and Gordon certainly seem excited), it's key to have as many of those top 5ish looking assets as possible, since stars get disgruntled and want out all the time, or teams want to move on from them.
If that's the price, having assets that are TOO good becomes a problem, because teams want them. If the Celtics had drafted Fultz, they'd have Fultz, and Cleveland would probably have wanted him as the centerpiece of a trade for Kyrie. Instead, they had Tatum, BKN 2018, and LAL/SAC. All of those assets are worth less than the consensus #1, and by all reports, Cleveland was fine taking ANY of them in the deal, so the Celtics chose the one they valued least to send out.
tldr; the Fultz trade looked like a bet on player evaluation, but really it was a bet on the price for stars remaining a top 5 pick plus pieces. If that's the price, you want as many of those as possible, as long as you're reasonably confident Tatum won't look like a turd immediately.