They can, but not only hasn't it just gotten harder, Dame has to be willing to continue being patient.
It's true in large part.
However, it's only as difficult as Dame makes it.
Unfortunately, anything short of Dame coming out and saying "I'm completely on board with what the Trail Blazers are doing. I love the idea of facing the challenges and mentoring a guy like Scoot. It was the best move for the team and I am all about the team." is going to be interpreted by pundits, fans of other teams and even Blazer fans in their own lens. Heck, even when Dame comes out and says he embraces the grind, he's not requesting a trade, I plan to be playing for the Blazers, he wants to play his entire career here and his goal is to win a championship with the Blazers, our own fans and fellow board members take the parts of it that suit their perspective, leave out the rest and approach it like it came from the oracle of Delphi.
None of us know what Dame really thinks or feels or if anything's changed or not. One would hope he and Cronin and ownership have had honest discussions about it. If they had, there shouldn't be a problem. We all can be blind fans or chicken littles as long as the most important parties are on the same page.
People can say "Dame doesn't want to look like the bad guy." Maybe there's truth in that, but it doesn't really hold water to me. I don't think more than 1% of Blazer fans would hold it against him if he said "You know, I really wanted to win a championship here, and, even if I didn't, chasing a championship with an organization facing bigger challenges and being a full part of the community away from the court meant more to me. But, over the last couple of years, my perspective changed, and I really want to feel what it's like being on the court having a role in determining who wins Game 7 of an NBA Finals, and I don't think I can do that in Portland, but it's become the most important thing to me now that my career is inevitably drawing to a conclusion." A few people would be butthurt and roast him for saying one thing and going back on it, but I think the vast majority of Blazer fans could understand and respect that.
Anyway, yeah, it all comes down to what Dame wants and how he wants to play it. This doesn't have to be contentious and/or shrouded in secrecy if he doesn't choose for it to be.