Almost every trade Ainge has made in the last ten years has initially looked like a loss to the Celtics' side of things except for the KG trade. Even the KG trade had some vocal negative opinions going against it, though, it was a minority.
Walker deal way back when? People wanted Ainge fired instantly, lol, even though he just got the job. Years later, it is looked at as good/fine value.
#7 pick for Telfair, Ratliff? Even though we used Ratliff's contract to get KG, this was a clear win for Portland from a value standpoint. They ended up with Brandon Roy. I can't even say Ainge won this in retrospect honestly unless you truly believe the KG trade would have never happened without Ratliff's contract.
#5 for Ray? Everyone HATED that deal when it happened. The KG deal made it fine in retrospect, but everyone thought the #5 pick was one of the main assets in a potential KG deal so when it was dealt for Ray, things got heated around here, and Boston was laughed at nationally.
Perkins for Green? Again, a lot thought we lost this deal, or at worst it was even and fit the needs of both teams.
KG/Pierce for BKN treasure? Another deal that people thought we lost. There were rumors that we almost got Jordan AND Bledsoe, so when we ended up with Wallace and 4 draft picks, a lot of people wanted to roll Ainge's head.
Rondo/Powell for Crowder/DAL pick/Wright/Nelson? People absolutely hated this deal, and Boston was laughed at nationally again. "If that's all you could get, why didn't you trade him earlier?!" was a common question asked back when the deal was made.
All of these deals had something in common. Boston was almost always seen as the winner in hindsight, but in the moment, they were almost always seen as losers. I'm not sure how that is Ainge trying to "fleece" anyone. It sounds like Ainge just knows how to value other teams' assets than the other team themselves, which may be really scary to opposing GMs.
The only deal where it was absolutely clear Ainge fleeced a team at the moment the deal occurred was the deal for IT. Ainge took advantage of his former pupil who completely mismanaged the guard rotation.
Even last summer, we were going to give up one of the BKN picks, 15, 16, and another first rounder or early second rounder for the 9th or 10th pick in a draft. That's insane value. No fleecing there at all, yet a few days after the 2015 draft, Cho came out and said (paraphrasing), "if a team is so willing to trade all those picks, is it really that great of a deal for us? is it really as much of a no-brainer?" IMO, it always sounded like a GM who was just scared to make a deal and overthinking the fact that Ainge almost always retrospectively wins trades.
The KG trade was definitely a win for both sides no matter how much people want to change that in hindsight. Minny received a 20/10 big man who was 22 years old for an aging Garnett who they had no shot at rebuilding around any time soon. If they played their cards right, they could have had a core of Curry, Rubio, Love, and Jefferson within two years of trading KG. They messed up all by themselves.