The only way I see the Celtics trading for Lillard is if the negotiations with Brown over his extension sputter, and the team looks to trade him. But does Portland do that deal? Brown would essentially be on an expiring deal, and the Blazers would be hard pressed to sign him once he becomes a FA. They'd probably ask the Celtics for draft picks in addition to Brown, which then starts to become dicey since you'd be taking on a massive contract for a player that's entering his mid-30s. All of this together, and I just don't think it's likely.
Brown's contract, willingness to sign would be a factor but I am not sure POR would get a better deal. They would still be in position to offer the most when Brown became a UFA. Brown would clearly be "the man" with some good young players around him and Jerami Grant. It would be a tough decision for POR but I think worth the risk, if the alternative is Tyler Herro, Duncan Robinson and a bunch of picks.
Not by a lot. The difference in the first four years of a contract extension between his incumbent team and whoever signs him would be less than 8 million dollars the first four years. The MAIN difference would be the extra fifth year at the end which would be like in the 58 million range for his age 32 season. But at that age he can probably make it up the difference on his next contract anyway anyway by signing a 3+1 and getting back to free agency earlier.
Like I said, it depends a lot on what the other options are and how truly motivated that POR is to trade Lillard. If Brown signals that absolutely no way he would resign in POR, then I agree, the deal is dead. But I am not sure it would play out like that. Maybe.
But if Brown says I am not committing to resigning, I will explore my options, including resigning, at the appropriate time, then maybe it is a risk worth taking for POR.
Ya my main point is that for a team that's going to be bad next year I just can't see a situation in which trading for a guy who can't be extended right now in Brown makes any sense. Almsot regardless of what Brown tells you its too big a risk.
Third team. Of course I can’t suggest which one but Brown should be a lot more desirable to a third team than Herro.
Mostly, I see POR running into the same problem with Jaylen. If Jaylen is only willing to stay if his new team is a contender, that limits the number of teams who can pursue him. Most of those teams do not have attractive trade proposals for POR. Most of them have older vets who are not of interest to POR. Like MIL with Middleton & Jrue. That type of thing. Teams that do have good young stars mostly have PGs (Trae, Morant) which POR already has with Scoot Henderson.
Here are the best ideas that come to mind:
(1) Maybe Cleveland could be convinced to trade Donovan Mitchell for a bigger wing to make their roster construction / balance better.
(2) Golden State could be an option. CP3, Kuminga, Moody & picks.
(3) Maybe POR has a shot at getting Minny to part with Towns if they are bringing Jaylen back instead of Lillard. An A Edwards / Jaylen / Gobert big three is interesting.
One and three are far from a given. The GSW one is the only high likelihood package available. Not that different from MIA's trade package of Herro, N Jovic, J Jaquez & picks.
Could OKC or NOP get involved?
(4) Would NOP trade Zion or Ingram if bringing back Jaylen?
(5) Would OKC part with Giddey & Jalen Williams in order to get Jaylen Brown?
I like the NOP one. They seem to want a change and are sick of how injury prone their two forwards are. So solid likelihood they'd be on board for that.
The OKC one is a tougher sell. I'm not sure I do that if I am OKC. I like the passing and team offense they are developing there with Giddey and Jalen Williams alongside SGA. They have Chet as a future star PF. Good quality with Dort and a young guard in Cason Wallace. I'm not sure I would disrupt that for Jaylen Brown. Then again, Jaylen and SGA could have Tatum & Jaylen vibes.
G: C Wallace
G: SGA
F: Jaylen
F: Chet
C: (future center)
That is a strong looking team.
I love the variety and versatility of their current cast of characters though. Feels like cutting off options early in the process to trade away key pieces for Jaylen at this point in the game. And without a key center yet to make such a win-now move worthwhile.