Damian Lillard is Where He Wants to Be

With the contract extension behind them, Lillard and the Blazers can focus on the future.

LAS VEGAS—Over the past three seasons, it's been difficult for most people in the NBA sphere to take Damian Lillard at his word that he actually doesn't want to leave Portland. That goes for fans, analysts at major national media outlets, social-media commentators, front-office executives at rival teams, everyone.

Lillard kept talking about his desire to stay with the Trail Blazers because he kept getting asked about it, because in 2022 the ecosystem of the NBA has reached the stage where the default is that every superstar in a small market is eventually going to ask out—and if they don't, the possibility of a future trade demand has to be manufactured to feed the news cycle. A comment Lillard made on Instagram during the 2020 bubble about Paul George "running from the grind" has become a meme at this point.

So when Lillard has said, over and over again since last training camp started, that even though the Blazers aren't currently title contenders, he isn't angling to go somewhere else, the reflexive response has been, "Are you sure?"

Three things stood out to me in Lillard's Saturday afternoon press conference announcing his brand-new two-year, $122 million extension, which is added onto the three years remaining on the last extension he signed in 2019 and keeps him under contract in Portland until 2027 and that general manager Joe Cronin said would make him a "lifetime Trail Blazer."

One was Blazers head coach Chauncey Billups, in his opening statement, pointing out just how unusual Lillard's commitment to Portland is.

"Superstars in our game today are different from superstars in my generation in the way they’re taking ownership of their careers," Billups said. "There are a lot of superstars that, if they don’t want to be somewhere, they find a way to get where they want to go. And Dame has been very clear about his intentions and wanting to be in Portland. I’ve got a lot of respect for him for that because it just doesn’t happen."

The answer to a question about Lillard's role in the growth of the NBA over the past decade was also illuminating. The part of his response that's gotten plastered on every social-media aggregator account is when Lillard said "the character and the fight and the passion and pride" are missing among today's players. But what he said next was much more interesting to me.

"There’s something there for being committed and having your heart in the right place," Lillard said. "Hopefully it will have the impact going forward on players, seeing that it doesn’t have to be, the media says this, and you just get swayed into doing what everyone else is trying to convince you to do. Everyone [else] doesn’t have to live with those decisions. I’m proud to be the person that jumps out, and this organization has shown that type of trust and faith in me. That’s what I hope will reach the guys that come behind me."

I'm not a huge "what's good for the league" guy and get annoyed when fans, reporters and anyone who isn't an ESPN or Turner executive or employee of the league office spends too much time publicly litigating TV ratings and talking about which playoff matchups Adam Silver is hoping for.

But as someone who grew up with Kobe Bryant, Tim Duncan and Dirk Nowitzki having Hall of Fame careers playing for one team, I wouldn't hate it if the pendulum swung back in that direction from the constant cycle of round-the-clock speculation about trade demands. I hope Ja Morant, Anthony Edwards, LaMelo Ball and Evan Mobley stay where they are for a long time, not because it's "good for the league" but because this stuff gets exhausting to talk about year after year.

That's also why it was eyeroll-inducing, for someone who has covered this team and this player for a long time, to hear that Lillard "deserves" to be set free and go to a team where he'd have a better chance at winning a ring. He isn't being held hostage in Portland. If he were to reverse course on all of this and ask to be moved, I believe that Cronin would be willing to do right by him for all he's done for the franchise and get him to a good situation. But Lillard has never asked for that and, given how strongly he's tied his personal brand and public persona to being "the guy who stayed," it's safe to guess he's never going to ask for it.

"Let’s say I do end up winning [somewhere else]," Lillard said. "I know me better than y’all know me. Of course I’d be happy with it, because anybody would be happy to win a championship. But it wouldn’t be as fulfilling to me as I would want that moment to be. And because of how I feel about that, that’s where I’ve always stood and that’s where I stand."

The other memorable moment from the press conference came from a question I asked him, one that I had a pretty good idea of how he'd answer. Now that he's signed this extension and talk of his potential unhappiness in Portland is in the past, I wanted to know when over the past decade he came the closest to wavering on his commitment to being a Blazer for life.

"If there was ever a time, it was last summer," Lillard said. "I wasn’t even saying, ‘I want to go somewhere.’ It was more, I’m putting my best foot forward every time, and I wanted a real chance to win. After losing to Denver, they were a beat-up team and we were pretty much at full strength. So losing that one … I was just frustrated, not having a chance. I was like, ‘We’ve got to put ourselves in a real position to have a chance.’ That was where I was at with it."

Last summer, the chatter about Lillard possibly wanting out wasn't meritless. That first-round loss to a Denver team without Jamal Murray or Michael Porter Jr. was followed by the firing of longtime head coach Terry Stotts justified by a claim that first-round exit was "not a product of the roster," which was followed by a coaching search that was handled as badly as a coaching search can be, which was followed by a free-agency period without any real improvements to the roster certain parties claimed was not the reason for yet another playoff disappointment.

During his training camp with Team USA before the Tokyo Olympics, Lillard multiple times was noncommittal about his future. It was hard to blame him for wondering whether it was really worth it to stay with an organization run by someone who cared more about being right about his draft picks than about building a winner.

Those questions continued into the season, amid front-office changes and a massive trade-deadline overhaul. Asked on Saturday about his trust in Cronin, he said: "I think I’ve got a good nose for when somebody’s blowing smoke and BS-ing me. I didn’t get that type of vibe. I trusted it." It wasn't hard to figure out who he was comparing Cronin to.

The rest of it was what you'd expect. Lillard feels great after the core muscle surgery and believes "one thousand percent" he'll be a better player now than he was before. He enjoyed the mental break and the time off to spend with his wife, Kay'La, and their three young children, all of whom were in attendance for the press conference. He loves the Blazers' offseason pickups of Jerami Grant and Gary Payton II.

Is this team a title contender? By Cronin's own admission, they're not there yet. But they're trying, which is all Lillard wants and is more than could have been said in the past few years.

"I just want a shot at it," Lillard said. "And if that happens, and it doesn’t work out, I can live with that."