Damian Lillard Says He Plans to Retire with Blazers: 'We'll Have a Chance to Win'

Damian Lillard has said he's staying with the Portland Trail Blazers over and over—and then he's said it over again, in case you didn't hear it the first two times.

Well, let him once again put any speculation to bed: He plans to finish his career in Portland.

“Yes, I do,” Lillard said on the Dave Pasch Podcast. “I’ve had my share of people saying ‘Man, you got to get out of there! You’ve got to do this, you’ve got do to that.’ But I’m the type of person that I’m never going to be marching to the beat of nobody else’s drum. I’m gonna always do what I feel like is in my best interest and that I really feel in my heart.

"I’ve said this on many different occasions, they call it ‘He’s being loyal!’ and ‘Loyalty this, loyalty that’ and I’m like, I’m naturally a loyal person but I do have a level of loyalty to the organization, but this loyalty that they’re talking about is ultimately to who I am as a person. I’m being loyal to who I am and not getting beside myself because I’m somebody that, I believe what I believe. I think I can get it done. Now, everybody else might say, ‘There’s no way the Blazers will ever win. They need to do this, they need to do that.’ But that’s just not how I feel about the situation. I feel like we’ll have a chance to win, I feel like that moment is going to come, I feel like that opportunity is going to come. And that’s that.”

Lillard signed a two-year, $122 million extension with the Blazers in July that could keep him with the franchise through the 2026-27 season. He will be either 36 or 37 by the time his contract expires, at which point it's almost certain Lillard will have spent the entirety of his prime with the Blazers.

Portland is coming off a miserable 2021-22 campaign, finishing 27-55 as Lillard missed 53 games due to an abdominal injury. It was the first time in Lillard's career that he failed to play at least 66 games.

The Blazers overhauled their roster with their star on the mend, jettisoning several veterans from the roster in moves that seemingly signaled a full-scale rebuild. While the additions of Jerami Grant and Gary Payton II will add some much-needed athleticism on the defensive perimeter, this is perhaps the worst on-paper Blazers roster ever assembled around Lillard.

Even the prize of last year's down season, rookie guard Shaedon Sharpe, is one of the rawest prospects in the lottery and is likely a couple years away from significant contribution.

Lillard says he believes the Blazers can win a championship during his career, but there is no obvious path to reaching that goal in the near future. It's possible Lillard has done the legacy math and decided he would rather be a legend in Portland than a champion. That's his prerogative and is arguably admirable in an era where players rarely have a true relationship with their city.

On the other hand, Lillard may start to change his tune once he reaches training camp and realizes how bare the cupboards are around him.