So the Bucks only had to give up Jrue Holliday and a 1st round pick and we apparently had to give up Dick and OG? That's kind of BS if you ask me.
From what I can piece together of the trade structure:
Bucks give: Jrue Holiday (POR), Grayson Allen (PHX), 2029 1st (POR), TBA Pick Swap(s) (POR)
Bucks get: Damian Lillard (POR)
Blazers give: Lillard (MIL), Jusuf Nurkic (POR), Nassir Little (PHX), Keon Johnson (PHX)
Blazers get: Holiday (MIL), Deandre Ayton (PHX), Toumani Camara (PHX), 2029 1st (MIL), TBA Pick Swap(s) (MIL)
Suns give: Ayton (POR), Camara (POR)
Suns get: Nurkic (POR), Little (POR), Allen (MIL), Johnson (POR)
Portland trades away their centerpiece and gets a flippable asset (Holiday) a young starting C they can try to rebuild and integrate into their young core (Ayton), and futures.
Phoenix appears to mostly be here for salary redistribution purposes, but turns that into transforming a guy they had soured on (Ayton) into a whole whack of depth pieces to work around their win-now setup of Booker/Durant/Beal. They didn't need splashy names, they needed quality role players and Nurkic, Allen, and Little could be those.
Bucks give up Holiday, Allen, 1st that's 5 drafts away and a pick swap that presumably comes within the next 4 years or so for Lillard on the gamble that he won't immediately revolt and whinge his way into a re-routing trade to Miami because he has to get his way or nothing.
Yeah from a pure talent perspective that's probably worse for the Blazers than OG, Dick, 1st(s) and swap(s) but the advantage for the Blazers is that by factoring the Suns into the trade they aren't taking any salary ballast like they would've had to with the Raptors (and the stuff the Raps would've had that they could trade off would likely not have fit onto Phoenix if they're the facilitators in this deal) and Holiday is a good high-demand type player in his prime(ish) on a contract that has a player option for next season, making him an attractive trade deadline flip piece.
Jimmy can claim tampering all he wants, but it's not tampering for the Blazers to choose not to trade him to Miami even if that's where he wants to go and even if the offer is "worse" (it's not really worse than the Heat offering Herro, picks, and scraps). Portland is free to make whatever trade they want and unless Lillard had an NTC then he just has to suck it up and either play out the couple of years left on his deal, work with Milwaukee to sort out another trade if they'd abide, or pitch a fit and refuse to report and look like a jackass.
Also while people are dreaming of Lillard, I don't think that would've been a trade that helps the Raptors. Let's say the hypothetical deal, based on just getting Lillard and matching salaries in a 2-team deal, would've been:
Raps get Lillard
Blazers get OG, Dick, Chris Boucher, Thaddeus Young, assorted futures
Now the Raptor lineup is:
PG: Lillard, Schroeder, Flynn
SG: Trent, ???
SF: Barnes, Porter
PF: Siakam, Achiuwa, McDaniels
C: Poeltl, Koloko
That's... not really that good. Instead of being a 7-12th place team they maybe move up to 5th-8th but are still not deep playoff threats. Alternatively you could take Young and Boucher out of the trade and give up Gary Trent instead, but then you've got no SG depth at all, Boucher slots back in at the still-jammed 4/5, and Young is just a dude at the end of the bench. And while Lillard hasn't voiced intent to stick it to Milwaukee like those rumors suggested he might in non-Heat trades, I can't imagine he'd be happier coming to the Raptors in
that shape than he would be going to the Bucks.
Eric Koreen wrote about this on the Athletic and I agree that the Raptors were really not in a position to capitalize on Lillard. People have acted like this is a Kawhi situation but the Raptors added Leonard to a team that had stupid good depth, had just won nearly 60 games, and really only subtracted Poeltl out of the rotation once you consider that Kawhi replaced DeRozan
and they added Danny Green. This current Raptors team was pretty much .500 and with VanVleet gone they have junk depth that would be stretched even thinner thanks to the trade. That's not a recipe for success.