Damian Lillard is an optimist. At least he was optimistic Wednesday, hours before a disappointing loss in Boston, where I caught up with him on the TD Garden floor. Despite Portland’s rocky season—31–35 entering Friday-night’s game in Philadelphia—Lillard still believed the Trail Blazers could salvage it.
“It looks like we’re struggling, but there are [five] teams with 33 or 34 losses,” Lillard says. “So it looks like, ‘Oh, you know, trying to get a play-in spot.’ But everybody’s playing each other and everybody’s in the same thing. We could end up fifth. In a perfect world, it’s possible. Right now, we just have to keep fighting and try to be one of those teams that comes out on the other side.”
This isn’t a column calling for the Blazers to trade Lillard. Or for Lillard to ask for a trade. That story is old. Tired. Done. Lillard is committed to Portland. He has said so publicly. He has contractually locked himself in. He plays to win championships. He is just hell-bent on winning one with the Blazers.
The question is, how do they do it? Portland has some nice pieces. Anfernee Simons can score. Matisse Thybulle can defend. Jerami Grant can do both. The Blazers have dealt with injuries over the season like most teams. But if the playoffs started today, Portland would not be part of it.
“It’s just been one of those seasons for us where we have had a lot of adversity,” Lillard says. “We haven’t been able to hit our stride at any point in the season. That’s the first time I’ve ever experienced that in my career.”
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Lillard needs help. It’s Portland general manager Joe Cronin’s job to get it for him. Cronin is in his first full season as the Blazers’ top basketball exec, a job he ascended to after Neil Olshey was fired in 2021. His tenure has been … unremarkable. He traded CJ McCollum—a move that needed to happen—netting what amounted to Josh Hart and a first-round pick. He flipped Hart for Thybulle and Cam Reddish. His wheeling and dealing has so far amounted to little more than a shuffling of deck chairs.
It will take a well-executed plan to get Portland to a championship-caliber level.
Does Lillard see one?
“I definitely can understand what the plan is,” Lillard says. “Me and Joe, one thing we do have is transparency. He knows what I want. I want to win. I want to win in Portland, and he’s expressed the same to me. He’s told me, ‘We want to give you every opportunity to win.’
“But there comes a time where we have the right intentions, [but] we’ve got to execute. We have to actually make that come to life, to give ourselves a chance to really make a run at it. And because of who I know him to be, I trust him on that. I don’t ever think he would tell me one thing and then not do it. If anything, it would just be like, ‘We did our best and we couldn’t do it.’”
And what happens then?
“I think I’ve always been firm in my commitment to what I want and to this organization, and that’s where it stands right now,” Lillard says. “But like I said, if it comes time where they say, ‘Man, we can’t get it done, maybe it’s time for us to turn a page,’ I don’t think that will be the case, but we’ll see. Right now, all I know is I want to win.”
It’s not impossible. The most important piece of a title contender is a franchise player. Lillard is it. He’s 32 and remains at the peak of his powers. He is averaging career highs in scoring and field goal percentage. He is taking 11 three-pointers a game and making 37.5% of them. Some wondered whether the injury that interrupted the 2021–22 season was a sign of decline.
For Lillard, it was rejuvenating.
“I feel as good as I felt in a long time,” Lillard says. “Dealing with that [abdominal] injury, it was just stressful. Because I knew I wasn’t right. Being up late, being sore all the time, not being able to move, knowing I was limited, not knowing how my body was going to respond and s--- like that. That was stressful. I’ve been able to just be a lot more clear mentally just knowing that I’m strong and I’m healthy.”
Lillard’s focus now is getting to the play-in, to the playoffs and seeing whether a healthy Blazers team can surprise in a wide-open field. But he knows next offseason is a big one. There will be opportunities to upgrade. Portland could have as many as two first-round picks in June and a cache of second-rounders to deal. If a needle-mover becomes available, Lillard wants the Blazers in the mix for him.
“That means we go into the offseason and we don’t come out the way we have in the past,” Lillard says. “Where it’s like, ‘Oh, we’re going to try to do something,’ and then we watch other people capitalize on things that are out there, and we pass, pass, pass, pass and can’t get anything done and then it’s done.
“It’s like, ‘All right, well this is what we got going into the season with.’ And I think as far as execution, that means we go out there, we be aggressive and we try to actually get something done. Stepping out there and giving ourselves a chance to be one of those teams in the end.”
Lillard isn’t putting a clock on his career. His contract runs through 2027, and he still enjoys the game as much as he ever has. But he has three kids, including son Damian Jr., who will turn five this month. His FaceTimes with his father, wondering when Lillard is coming home, can sting. The end is nowhere close, but Lillard knows it’s coming.
“I would like to win a championship before that,” Lillard says. “So I’m not looking at any timeline, but I’m not going to be one of these dudes out here stretching it out. I’ve made plenty of money; I’ve accomplished a lot. I just want to win a championship and then just go from there.”
