Damian Lillard, Trail Blazers extend union with an eye toward a championship: ‘I just want a shot at it’

LAS VEGAS — Damian Lillard’s decision to sign a two-year, $122 million contract extension that will lock him in with the Portland Trail Blazers for at least four years came down to several factors.

1. Lillard’s belief in the Blazers’ commitment to winning a championship.

2. Two major roster additions this offseason.

3. And, yes, the money isn’t bad, either.

Lillard, general manager Joe Cronin and coach Chauncey Billups held a news conference Saturday at the Thomas & Mack Center prior to the summer league team’s second game against New Orleans.

Each smiled and oozed mutual admiration while expressing belief that this trio atop the team’s power structure has what it takes to steer the franchise toward its first championship since 1977. The financial commitment demonstrated that chair Jody Allen and vice chair Bert Kolde have similar faith.

Lillard said he was grateful to remain with the organization and takes pride in being a Trail Blazer.

“I get a lot of people on the outside telling me what I should do, telling me everything that goes against what I believe and what I stand on,” he said. “Just to have people that believe in that along with me and believe in me being able to accomplish what I want to accomplish, it means a lot. I think us extending this contract and coming to this deal shows.”

Cronin and Billups, each with one year under their belts in their respective roles, had to earn Lillard’s trust to make this happen.

“This deal puts us in a position to continue on the path to making him a lifetime Trail Blazer,” Cronin said.

Said Billups: “We’re trying to build our team up so we can give Dame and our great fans a fair shake and a fair chance to accomplish what we all want, which is a championship.”

Lillard had three years remaining on his current deal, worth about $137 million. He is now locked in at five years at about $259 million, with the final year (2026-27) being a player option worth $62 million.

Lillard, who turns 32 next Friday, will be 36 at the start of the final year of his contract. That means the clock is ticking on both his prime and the Blazers’ window for winning a championship with him as their leader.

For Lillard to sign an extension with Portland, he had to see evidence from Cronin and Billups that they were committed to winning. That put the pressure on both to convince the superstar guard while also dealing with a tumultuous season. Neil Olshey, former president of basketball operations, was fired. Lillard was lost for the season following core surgery. CJ McCollum and Norman Powell were traded. The Blazers finished 27-55, the sixth-worst record in the NBA.

Such turmoil with a franchise often causes players of Lillard’s caliber to jump ship. Billups said that today’s superstars are different from when he played starting in the late 1990s. They have the power, he pointed out, to dictate where they play. So, for Lillard to remain committed to Portland, and in the face of franchise-wide adversity, is something that shouldn’t be taken for granted. Nor should his commitment to winning.

“Dame has been very clear about his intentions of being in Portland and playing in front of the Portland fans,” Billups said. “I’ve got a lot of respect for him for that because it just doesn’t happen. In our game today, you have two kinds of teams. Teams that have a superstar and teams that are looking for one. And we’re lucky enough to have one that wants to be here.”

Lillard at times in his career definitely could have moved on and chased a title as many stars do. But that’s simply not who he is.

“I don’t think that you earn something like this just by going out there and scoring a bunch of points,” Lillard said. “Something that’s missing in our league is the character and the fight, and the passion and pride about not just the name on the back, but the name on the front and how you impact the people that you come in contact with.”

Remaining prideful in those things, he said, has its rewards.

“I think this just shows the power in that there’s something there for being committed and having your heart in the right place and having your mind in the right place,” he said.

But to be clear, Lillard only wanted to remain in Portland if the Blazers showed a commitment to winning. He made that clear last summer and throughout the season.

“I wasn’t even saying, ‘I want to go somewhere else,’” he said. “I was just like, ‘I’m putting my best foot forward every time and I want a real chance to win.’”

After the 2021 playoff series loss to Denver, Lillard said he became extremely frustrated.

“Watching other teams win the championship, I go into the shell after a team wins and then the parade is everywhere,” he said. “I can’t handle my jealousy and frustration when that happens. So, at that point, I was really frustrated.”

But Lillard knows that ultimately if he left to win a title elsewhere, it wouldn’t be as fulfilling as winning in Portland. He simply wants a chance at winning.

“As long as I have an opportunity to do it, I’m willing to go out however,” he said. “That’s where I’ve always stood and that’s where I stand. I just want an opportunity to either, it’s going to get done or it’s not going to get done. I don’t want to go out there with this crazy uphill battle that I’m fighting and we need a miracle times 10 to get it done. I just want a shot at it. And if that happens, and it doesn’t work out, then I can live with it.”

Lillard believes that the makeup of the team is trending toward giving him that chance. Especially after the Blazers have made two moves this offseason that instantly upgraded the roster.

First came trading for Detroit forward Jerami Grant, a good friend of Lillard’s.

“I think getting Jerami was huge,” Lillard said. “On the wing, you have to be deep. You’ve got to have guys that are athletic, guys that are versatile. And Jerami is a guy that was on winning teams in Denver, he was on a winning team and Oklahoma City, and going to Detroit and having a lot more responsibility for that team that he had on any other team, I think that forced him to grow into a better player. So now coming back to us, filling a role that we needed, and a guy that will be able to do that job better than what we’ve had, I think it automatically improves us as a team.”

Next came the signing of Gary Payton II, a defensive-minded guard much needed for what was one of the worst defensive teams in the NBA last season. Lillard, who is from Oakland, California, many years ago forged a strong relationship with former NBA great Gary Payton, also from Oakland. That led to Lillard getting to know Payton II.

“Just a dog, tough,” Lillard said of Payton. “He just impacts the game. He changes the team. He’s coming off of a championship with a team that he had a lot of impact on. So, us being able to get him too, I feel very good about that.”

While those two additions brought a smile to Lillard’s face, Cronin has said that the franchise must do more. Lillard said he has the confidence that Cronin and Billups can get the job done based on numerous conversations with both regarding wanting to win.

“The answers that I got and the responses that I got, I didn’t look at him, like, ‘Oh, he’s just telling me this,’ I was able to trust what I was hearing from Chauncey and Joe,” Lillard said. “And I think I’ve got a good nose for when somebody is blowing smoke.”

— Aaron Fentress | afentress@Oregonian.com | @AaronJFentress (Twitter), @AaronJFentress (Instagram), @AaronFentress (Facebook).

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