Skip to main content

Rift growing between Portland Trail Blazers star Damian Lillard, general manager Neil Olshey

A report this past weekend outlining growing dissatisfaction from Portland Trail Blazers star Damian Lillard relating to the direction of the organization has led to a ton of trade rumors surrounding the six-time All-Star.

Is it possible that that the generational talent wants out from the Pacific Northwest and will request a trade this summer? After the process that led to embattled Blazers general manager Neil Olshey hiring Chauncey Billups as their new head coach, anything seems possible.

The backdrop here is a team that is coming off a fourth first-round exit in the NBA Playoffs in five years. Simply put, Damian Lillard wants to contend and he’s not sure it’s going to happen in Portland.

Now comes this note from Ian Begley of SNY suggesting that Dame and Olshey have not seen eye to eye recently and are not considered terribly close.

“One element here that I’ve heard is, with Lillard and Neil Olshey, they have not totally seen eye-to-eye in Portland,” Begley noted. “A couple players around the league have kind of jokingly said, ‘If you like Portland, if you like being in Portland, don’t get close to Dame because you might get moved.’ Over the course of Lillard’s tenure, we’ve seen players that he’s been close with not remain on that roster, whether it’s via trade or signing somewhere else in free agency.”

This was part of a broader conversation from the New York Knicks’ insider discussing the possibility that Lillard could end up in the Big Apple this summer. It also can’t be considered too surprising.

Neil Olshey is the problem in Portland

NBA: Brooklyn Nets at Portland Trail Blazers
Nov 8, 2019; Portland, OR, USA; Portland Trail Blazers General Manager Neil Olshey looks on during warm ups before the game against the Brooklyn Nets at Moda Center. Mandatory Credit: Steve Dykes-USA TODAY Sports

Let’s get this out of the way right now. Even after attempting to throw former head coach Terry Stotts under the bus following his firing, those around the league don’t have a good opinion regarding Olshey. Previous free-agent signings and a lack of accountability on his end adds to this.

The backdrop here is a Blazers hierarchy void of leadership since the death of owner Paul Allen. His sister, Jody Allen, has since taken over that role. She is seen as more hands-off than her brother. That has led to a power gap needing to be filled, one that Olshey has more than been willing to pick up.

This was taken to a new level after reports suggested Allen wanted Becky Hammon to be the Blazers’ next head coach. Now that there’s renewed questions about Billups’ previous sexual assault allegation and how Portland handled that in his introductory press conference earlier in the week, there’s no telling how Damian Lillard feels. Reportedly, he had no previous knowledge of the 1997 allegation before Billups was hired.

Will Damian Lillard request a trade?

Right now, this remains up in the air. Lillard has been as loyal as any NBA star in his nine years with the Blazers’ organization. He’s also pushed back against the idea of forming a super team elsewhere, acting as an outlier in that regard.

But there’s an argument that Dame has been loyal to a fault. Olshey’s struggles from a player personnel standpoint coupled with the Blazers’ irrelevance as it relates to being a top-end championship contender could lead to Damian Lillard finally coming to the conclusion that his time is up in Portland.

It’s one of the biggest stories as the 2021 NBA Playoffs come to a conclusion and what promises to be a hectic summer around the Association starts to heat up.

More About: