Damian Lillard wasn’t surprised by the question. How could he be? Nearly a decade in Portland, half of which has been spent by everyone wondering when Lillard was going to catch the next Alaska Airlines flight out of town. Never mind that Lillard has signed not one but two contract extensions with the Trail Blazers, the most recent a four-year, $196 million deal that keeps him tied to Portland through at least 2024. It seems everyone is waiting for Lillard to force his way out.
And so it was on Sunday, during Lillard’s All-Star media availability, that Lillard was asked—again—about his future in Portland. And he responded—again—that he has no intention of playing anywhere else.
“I think, for every person that says, You know I want to see him on the big stage, and I want to see him go to a bigger market and all these things, of course, those things have pros, but nobody ever wants to think about the cons,” Lillard said. “If you take that step and it’s not what it seems to be, and it doesn’t work out, or an injury happens, and you haven’t established as much of a rapport with that team, and they chose one guy over the next guy and now you’re traded to a third team, things can fall apart. That may never happen, but it’s just a lot of things you can’t control.”
What’s with the nationwide obsessions with Lillard? Is it because he plays in a small market? The Blazers rank in the bottom third of the NBA in media market size, stuffed in Kings/Hornets territory. You’re likely to seek out their games on League Pass only when your favorite team is playing them. Is it because Portland has not won in the nine years Lillard has been there? The Blazers' best finish was the Lillard-fueled run to the Western Conference finals in 2019. Four times Lillard’s season has ended with a first-round exit.
There’s a sentiment that Portland doesn’t deserve Lillard.
And that Lillard deserves better than Portland.
Lillard, clearly, doesn’t think so. All championships are not equal. The Blazers have not won one since 1977, when Jack Ramsey was the coach and Maurice Lucas the leading scorer. They came close in the early ’90s, when the Clyde Drexler–led teams came up just short, twice. They had a talented, albeit combustible, group in the late ’90s that ran into a pair of dynasties (Spurs, Lakers) at the end.
“For me, it just means a lot to be considered amongst the best players to play in this organization,” Lillard said. “Because there’s been so many great players here, and to win a championship because we’ve only won one and it’s been so long, that would just be the best ending for me.”
A title in Portland will mean something. This isn’t a slight toward LeBron James, Kevin Durant or the growing number of stars who have bounced around the league in pursuit of championship situations. Unless you have stayed in one job, in one city your entire life, you have no right to criticize the decisions of 20-somethings who do the same things you have. But if you ask James which championship means the most, it’s likely the one in Cleveland. If you ask Durant if he would trade his two titles in Golden State for one in Oklahoma City … well, I wonder what he would say.
Lillard wants that in Portland. “He’s the most loyal player in the league,” Blazers center Enes Kanter told Mad Dog Sports Radio. “Everyone is trying to go to big markets … you look at this guy and he is trying to prove all the haters wrong.”
And who is to say he can’t have it? Portland is 21–14, squarely in the middle of the conference playoff picture. C.J. McCollum, out since mid-January with a leg injury, is expected to return soon. Jusuf Nurkić, sidelined after wrist surgery, is right behind him. Portland has one of the NBA’s best young shooters in Gary Trent Jr. and some nice rotation pieces in newly minted Slam Dunk champion Anfernee Simons and second-year forward Nassir Little. And Carmelo Anthony—shooting 38.7% from three—continues to reinvent himself off the bench.
Could the Blazers get blown out of the playoffs early? Sure. They don’t defend anybody and the volatility of the standings means Portland could find itself (again) against a full-strength Lakers team in the opening round.
Could they make a run to the Finals? They have one of the NBA’s best backcourts, a roster that goes eight-deep with quality players and some flexibility to make a deal. Blazers GM Neil Olshey has upgraded the roster at midseason before (Nurkić, Rodney Hood) and Portland is armed with an open roster spot and some interesting young pieces to dangle. A reunion with ex-Blazer LaMarcus Aldridge—who could be bought out by the Spurs over the next few weeks—would be a fascinating one.
And they have Lillard, an MVP candidate and one of the NBA’s best closers. There’s seemingly little Lillard wants more than to win a title in Portland. He may not finish his career there—at 30, Lillard has a long way to go—but for now, he’s on a good team that with him leading it has a chance to contend.
It’s enough for Lillard.
It should be enough for everyone.
“I’m saying if everybody doesn’t think I can do it in Portland and we can’t win in Portland, what does it mean and what happens when we do?” asked Lillard. “If we actually go and do it, then where does that put me? Where does that put my legacy? Where does that put my career?
“And that’s how I see it. I want that day to come.”