Damian Lillard spent the first 11 seasons of his career with the Portland Trail Blazers, becoming a franchise legend and one of the NBA’s top 75 players over that time. But despite his 3-point prowess and penchant for hitting incredible shots in the game’s biggest moments, he never found true team success, reaching the conference finals only once.

In the summer of 2023, Lillard requested a trade to a championship contender. What followed was a three-year roller-coaster ride beginning with protracted trade negotiations, a surprising move to the Milwaukee Bucks, an imperfect partnership with superstar teammate Giannis Antetokounmpo and more playoff heartbreak. Then, in 2025, in the midst of a second straight first-round postseason exit, Lillard tore an Achilles. A few months later, Milwaukee made the shocking decision to waive Lillard with two years and $113 million left on his contract.

The ups, downs, loops, twists and turns ultimately led Lillard back to Portland, which signed him back in July 2025. Lillard says the Blazers were the first team to knock on his door after the Bucks let him go.

“I’m really thankful that as soon as I was waived, it was the first opportunity presented to me,” Lillard told NBC News on the eve of the season of how he ended up back in Portland. “They know that I can be counted on. They knew that I wasn’t gonna accept the injury and just be done. They knew how I was gonna respond to that.”

The path back to the Blazers certainly wasn’t easy. Lillard landed in Milwaukee on a team loaded with championship expectations. During his first season with the Bucks, the franchise changed head coaches. Meanwhile, his chemistry with Antetokounmpo — who has since been traded himself — was constantly called into question. Even as Lillard continued to average more than 24 points per game, the team couldn’t find consistent success. Injuries marred both postseason runs as Lillard and Antetokounmpo appeared in only four playoff games together — and won only one of them.

At the same time, Lillard dealt with personal struggles, once describing his time in Milwaukee as “lonely,” as his family remained in Portland. But he believes the three-year detour from the team that drafted him has ultimately proved to be beneficial for what most assume is the final act of his career.

“I don’t regret any part of the journey. I feel like it was all necessary,” Lillard said. “The team that I’m on now couldn’t be formed if I had never left. We would still be trying to find ways to get players, as opposed to having to rebuild, developing guys and having the assets to do that. That required me to go.”

He added: “I always look at things and I tell myself, whether it’s good or whether it’s bad, I’m always seeking out those opportunities to let my true character show and just keep rising. Whether something didn’t work out or whether I was criticized for something or whether people think I’m done, I’m always looking for the opportunity to show how real and how thorough I really am at heart.”

Lillard signed with the Blazers in the summer of 2025, but he missed all of last season as he recovered from his Achilles tear. He has since rejoined a team that made the playoffs without him last season. In the summer, Portland added former All-Star point guard Ja Morant, leading to another round of questions about how Lillard will mesh with a high-profile player.

So far, so good.

The Blazers enter their Tuesday tipoff with the Los Angeles Lakers (10 p.m. ET on NBC and Peacock) with a 2-0 record. Lillard is averaging only 28.5 minutes a night through the team’s first two games. He scored 25 points in Portland’s season opener and followed that up with 19 more in a win over Sacramento.

The Blazers have an eclectic roster that is being deftly managed by first-year head coach Micah Nori through two games. In addition to Lillard and Morant, Portland also has two-time champion Jrue Holiday (who was actually part of the Lillard trade in 2023) and former No. 3 overall pick Scoot Henderson in the backcourt. Rounding out the roster are up-and-coming big man Donovan Clingan, wing defender Toumani Camara and forward Deni Avdija, who was an All-Star last season.

To Lillard’s earlier point, his departure helped put the current roster together. The trade with Milwaukee led to the arrivals of Camara and Avdija. The subsequent rebuild landed the draft pick to take Clingan. And the Bucks’ decision to waive Lillard gave him the financial freedom to sign a team-friendly deal with the Blazers.

The result is a deep team that doesn’t force Lillard to carry the burden of winning on his shoulders.

“Everybody’s been selfless,” Lillard said. “You gotta expect that adversity is gonna hit. It’s gonna take sacrifice, all of the things that I think we all know and expect. But we got a super-talented team. One thing that I noticed already is how simple the game feels.”

Lillard said the variety of talent around him has been especially helpful, from the defensive tenacity of Camara and Holiday to the playmaking skills of Morant to Avdija’s ability to bulldoze his way into the paint.

Nori has leaned on the versatility of his roster. Granted, it’s very early, but of the 10 players who’ve appeared in both of Portland’s first two games, all but one are averaging at least 12 minutes. And no player has averaged more than Avdija’s 30.5.

In the team’s win over the Kings, Nori even pulled Lillard and Morant during a late possession to get more defenders on the court.

“That’s the good thing about having this group,” Morant said after that game. “Obviously, minutes got to be spread out. But if we all are unselfish, ego-free and just want the best way … there shouldn’t be no problems.”

Said Lillard of his new role: “I don’t feel overwhelmed with responsibility. The way our team is set up is set up for me to have a great season without having to kill myself like I might have had to do in the past for us to have success. I can get deep into the season and into the postseason feeling good and feeling healthy.”

It’s incredibly early. And the Blazers as a team haven’t yet faced any of the adversity that Lillard knows comes with an NBA season. But an opportunity is there, he stresses, both for him personally and the franchise as a whole. It’s the same opportunity that caused him to ask for a trade three years ago to begin with, an opportunity to win.

“I always look for that opportunity to show my true character,” Lillard said. “That’s how I look at the last couple years. And now I’ve arrived here, and I expect to have a great season. I expect our team to have a great season, and it’ll show what I’m explaining to you right now in the end.”