So I think sometimes we (this is a general thing and includes me, but definitely not everyone) make the mistake of going on Basketball reference and judging a players worth. Or judging what a players worth based on what the team accomplished with them. When there's more to it. I think part of what makes some guys get contracts worth more than what it looks like they deserve (on the court), is because of theres a lot more to it. Their's fit, there's personality, there is marketability, we tend to think of a team as Win's and Losses, and that's all that is important, but for professional leagues/franchises, it's more than that and sometimes a lot more to it. Teams are in it to make money, and yes winning definitely helps, but there are 29 teams every year who don't win a championship and those teams still have to find ways to fill seats, to sell merch, to get people to turn on their TV, they have to get people in the locker room who are likable.
In Dame's situation he will likely have the best Blazer career, represent the franchise better than all the others in consideration, have had some playoff success even if no rings, and will keep people interested much more than trading him for assets and hope. There is a very good chance that paying 34-35-year-old Dame is a "negative contract" in terms of basketball considerations, but paying him has positives, shows other stars that hey if I go to Portland and I'm successful I will get paid.
I completely understand the hesitation of paying really anyone a super-max, it's a lot of money, and basketball-wise it can create struggles to fill out the roster, but there are ways to do it. Look at Houston, they "could" have multiple max guys, does that mean they win a championship? No. It does mean that people in Houston will be paying attention though.