In case Portland Trail Blazers general manager Neil Olshey wasn't already feeling a level of pressure heading into the 2021-22 NBA season, Damian Lillard made sure to remind him of the task ahead.
"At the end of last season, I wanted to see our roster improve," the Blazers star told reporters at media day Monday. "We had our conversations about what that might look like. I come into this season with faith that that will happen."
Ahead of competing for Team USA at the Summer Olympics in Tokyo, Lillard denied he had requested a trade from the Blazers. While that provided some level of reassurance for Portland, it's never good when your best player has to publicly address trade rumors in the first place.
Lillard also made it clear at the time the Blazers needed reinforcements.
"I just think we've reached that point where it's like, OK, it's not enough," he said. "Do we actually want to win it all? Is that what we're shooting for? We've got to do things to show that. We've got to put action behind that. That desire to win at that level—that's been my only thing this entire time."
The franchise has a new head coach in Chauncey Billups, yet the roster remains largely unchanged from the one that couldn't get out of the first round of the 2021 playoffs—a fourth first-round exit in five seasons.
Acquiring Larry Nance Jr. from the Cleveland Cavaliers made the Blazers better, but Nance doesn't raise their ceiling much Likewise, having a healthy Jusuf Nurkic for a full season will only help so much within the context of contending for a title.
The problem for Olshey and the front office is that it's difficult to see a path where the Blazers get the kind of star who helps them achieve what Lillard is aiming for.
CJ McCollum is a proven scorer and perimeter threat, but the $100 million he's owed over the next three seasons means Portland probably can't get equal or more value in return.
The Athletic's Jason Quick reported in July some teams were "offering Portland a chance to get into the top part of the draft" for McCollum. Flipping an established veteran for draft picks doesn't fit with the Blazers' timeline.
Beyond McCollum, Olshey has little in the way of trade assets.
Getting Lillard to affirm his commitment to the organization was obviously good news this summer. But it may have merely delayed the inevitable because the Blazers appear stuck between a rock and a hard place.