It's going to weigh on him. It weighs on every good player the Blazers draft or obtain. The Blazers can't compete. They can't get the players here to truly compete. Other cities are more attractive. That's not an opinion, that's the truth. Portland, Oregon isn't where you want to be as a young, talented, millionaire basketball player. It's just not. It's cold. It's rainy. The fans and the local media are obsessive, invasive, and bi-polar. Damian could be different, but he's probably not. He's a level of player that wants to win. He will be sick of being the big fish in a small pond. CJ and Nurk are not enough. He's going to demand a trade. It may not be today, tomorrow, or soon, but it WILL HAPPEN. There's no "rebuilding". There's no "wait for players to develop". Lillard's prime is being wasted, and it is going to bite the team and the city in the ass.
Olshey HAS to swing for the fences. He has to drastically overpay for good players in trades. Everyone on this team not named Damian Lillard should be on the trade block, either publicly or privately. Other teams want CJ. But the FO and the fans are afraid. They want to cling to what they have, vs. take a chance on what could be. And that's the Blazers MO: Mediocrity is better than being bad, because local fans will still buy tickets to see a team that MIGHT win vs. a team that doesn't have a chance to win. That's the same for most small market teams, but in Portland it seems culturally ingrained. The only person with the balls to try to break that cycle in the team's history was Bob Whitsitt, and while he ultimately failed, it was a spectacular failure that was exciting while it lasted, and if not for a cold shooting quarter, might have just as easily succeeded.
With the West looking as it does... the future for the Blazers as they stand right now looks hopeless, as does Lillard's career here. Don't think he doesn't know it.