Damian Lillard’s future with the Portland Trail Blazers may be the single biggest question in the NBA this summer. Last week, a report indicated that Lillard plans on requesting a trade sometime soon, although shortly after that hit the internet, Lillard sat in front of the media and said that is not the case.
A new report from Jason Quick of The Athletic indicates that Lillard does seem to want to give Portland the chance to make things better, although that might be a mighty tall task. While the threat of him leaving “has never been more real,” Lillard reportedly wants “meaningful improvement” on the Blazers roster, something he has relayed to general manager Neil Olshey.
In no uncertain terms, during the long meetings and back-and-forth text messages, Lillard has informed Olshey he wants upgrades to the Blazers’ roster. Lillard literally lost sleep over the Blazers’ first-round loss to Denver this season, and he wasn’t sure everyone else in the organization was as pained as he is. So he wants Olshey to surround him with better players — and more of them.
Since Lillard became the franchise player in 2015, he has periodically delivered similar messages to Olshey. But this time, it is clear Lillard is more urgent, illustrated in part by his decision to do so publicly. And as Lillard has noted, he is now 31 and racing against time, which has intensified his thirst for a title.
The inherent the issue the Blazers have is that it’s hard to imagine how they can make a particularly big swing. It’s almost certainly not going to be in free agency due to their cap situation and they don’t have a pick in the 2021 NBA Draft, so they’d have to hope teams are interested in trade packages. The question then becomes whether packages headlined by veteran players (C.J. McCollum, Robert Covington, etc.) and younger guys (Nassir Little and Anfernee Simons) are appealing enough to bring in the level of talent Lillard wants.