Now that Lillard has requested a trade, Portland needs to go draft pick hunting. While four 1st rd picks would be ideal, I think Portland's best hope is to get 3 and a couple of veteran help and/or an expiring contract or two. In the end, it doesn't matter much, as nobody wants to live in Portland. Just burn the franchise down already, and move them to Vegas.
They can probably suck for one more year, get one more draft of high picks combined with what they'll get from Lillard, and then go forward with a young core. Get rid of Grant and Nurk as well although Nurk isn't going to get anything back. They're going to match for Thybulle which I also like. Eubanks as a backup center isn't the worst thing.
Simons, who has already made CJ expendable, Sharpe, Henderson and their next top picks have to completely bust out. No GM would give up on that for at least a few seasons.
End of the day, Dame + CJ didn't work and Collins was a bust due to injury. No real shame in that. They got Nurk for nothing and he didn't completely suck until after he snapped his leg. Aldridge leaving was a significant blow and he's stated publicly he regretted that. Spurs were an elite organization at the time.
Losing to Denver in 2021 and firing Stotts was the beginning. Need to get rid of Billups now.
That Grant contract is going to be a difficult one to move ... I suspect that he received a premium on the deal because 1) Portland needed to resign him to have any chance with keeping Dame happy and 2) Grant's camp knew that and inflated their ask accordingly.
Nurk is a contract worse than getting nothing back for ... you'd likely need to attach an asset to get that contract off the books.
Thybulle is probably worth matching but the question I'd have is what's the match, what's the term, and if it doesn't match the timeline what type of asset can you get at the trade deadline for him? I'm not sure that you're getting more than a 2nd rounder back for him.
Best case scenario is that Portland is able to get the kind of assets and cap space to be able to think of competing for the playoffs in 3 years. Reality is that it's probably going to be 5 before they are any good.
They will most likely have to keep Grant but I thought Nurk was on the tail end of his deal. It came post leg injury so I don't think it's a bad contract.
In the end they have a young core going forward and it's this GM's decisions. Last GM would only have Simons and Little (nothing contract), and Simons is a good piece.
Thybulle is a player you want, you don't sacrifice much for elite defense, and he's a young player. Overall the ages of the roster go pretty well together and you can get a veteran winner to come show them how to be professional.