We all seem to be forgetting how it works in the NBA today. The small market teams like Portland are really just a farm system for the glamour teams like the Lakers, Knicks, and Heat. We develop players like Lillard for a few years and then they're snapped up by some big market team as the final piece of their championship run.
It's fun to pretend otherwise, but this is the way it actually works. We can have fun cheering on our Blazers, but to act like they're ever going to win a championship again is just wishful thinking.