It's funny when people talk about Dame asking for an extention he can't even talk about now, but it's really funny when people are like "trade Dame, Portland is never going to win a title" (the same was said about the Bucks last year), or that they should just trade Dame and 'start over', as if that works.
Since 2012, the NBA has had 7 Champions. And for the WC, there has been 4 teams going to the finals (Suns, Lakers, Warriors and Spurs), with 3 winning the title.
That means in the 9 seasons since Damian has been a Blazer, 11 WC teams have failed to go to the finals.
What's that mean? You're much more likely to not make to the finals. Then you trade away the only reason the team is even remotely relevant now? And I'm betting their chances will be even worse to be a competitive team than it is now.