You have heard "two wrongs don't make a right". Nobody is saying that $28M couldn't be worse spent (Chandler Parsons, Nic Batum, etc); that doesn't mean they can't still be dissatisfied with it. What was paid to Meyers and Turner has nothing to do with what CJ's contributions are actually worth to this team.
I agree with this, and it was my takeaway as well. His comments about coaching staff were most telling for me.
It's 100% connected! If the Blazers were in Miami i would have a different opinion on CJ's contract. If you could make room for better players in the future then sure! why not?! If we get rid of CJ and we can't replace him with a top 30 player then we're talking about taking a step back. That money will go to overpaid role players instead of overpaid CJ. And what is "overpaid" anyway? There are 30 teams in this league and maybe 20 players who can actually lead a team. 2nd bananas (and even 3rd bananas) cost max contracts, that's the reality of the NBA.
OK, so if I understand correctly, your contention is basically that even if CJ is overpaid (which you're not conceding, and I understand that), it's OK because we're in Portland and we're not going to be able to do anything better with that money anyway, so it's better to pay CJ $30+M than to give Neil another chance to waste cap space on Meyers/Turner-level players. Do I have that correct?
Yes, but i never believe i'm 100% right. Reality is a bit more flexible, i'm just relying on what i know at the moment. I do want to say that if it was theoretically possible to get something like Matisse Thybulle+Richardson from the Sixers and then get the appropriate coach who will implement an amazing defensive system around Dame... then maybe i can see something like that working (if Nurkic is healthy) because it makes sense. But that kind of overhaul is too hard to accomplish in real life.
For all the credit Dame receives for being loyal to Portland, CJ has earned at least a small percentage of that same love. Sure he has flaws but let's not act like he's Dion Waiters or someone like that.
I think that if you accept the premise that Portland can't really use money to lure stars like bigger/sexier markets can, it's a reasonable point. It may be better to spend a little more inefficiently to get stars and near-stars then to completely sit out that end of the player spectrum and focus only on efficient expenditures of the middle and bottom end of the player spectrum (and it's often been said that many of the biggest mistakes in terms of value come with the mid-level players).