Damian Lillard Returns to Portland: An Exciting Return and Challenges in the NBA

Damian Lillard’s Triumphant Return to Portland: An Expected Reunion

In late July, more than 400 children gathered in a YMCA gymnasium in Beaverton, Oregon, for an annual basketball camp. The “Damian Lillard Basketball Camp” continued in Oregon, but in the last two years, it felt more like a fleeting reunion than an annual visit with the local star.

The campers’ most popular question was as touching as it was obvious.

When are you coming home?
Damian Lillard Campers

This time, that question wasn’t necessary.

A week earlier, it was announced that Lillard would sign a three-year contract to return to the Portland Trail Blazers, transforming the camp into a welcome party filled with joy. Most of the campers, aged 6 to 16, wore their Lillard jerseys, a mix of Milwaukee green and Portland pink. Lillard joked with those present, saying he had answered more questions about his return than about basketball drills.

In just two years, I probably wouldn’t have believed it. I’d be lying if I said I didn’t expect this to happen at some point, but that it would happen so soon, I didn’t expect.
Damian Lillard

This was the highlight of days of celebration for Lillard’s return. The social media team captured his return to the locker room and the moment he saw his locker, exactly where he had left it. Emotion overwhelmed him. Lillard always wanted to return to Portland, according to sources close to him, even before being traded to Milwaukee, he planned to end his career with the Blazers. Lillard’s return to the Blazers is one of the most touching stories of the NBA offseason, but a key question persists: after two frustrating and injury-filled seasons in Milwaukee, what will Lillard’s post-injury stage be like? When free agency opened in the summer of 2023, Lillard requested a trade from the only franchise he had known. Specifically, he wanted to join the Miami Heat to team up with Jimmy Butler and Bam Adebayo. The Blazers had finished 13th in the Western Conference with a record of 33-49, missing the playoffs for the second consecutive season. For years, Lillard and his agent, Aaron Goodwin, urged the team to improve the roster, but without success. In September, with no signs of a deal with Miami, Lillard began training at the Blazers’ facilities and reintegrating with the team. Goodwin informed the Blazers that Lillard would stay in Portland, but the team wanted to resolve the request before the start of training camp. A week earlier, Lillard was traded to Milwaukee.

More than anything, it was misunderstandings and lack of communication. Joe and I never talked about [a possible return]. It just stayed there and we let it be what it was, I think that was the mistake.
Damian Lillard

But a few months after the transfer, steps towards a possible meeting began to take shape. Goodwin and Cronin had a conversation in January, where they identified the gaps in their communication and said that, if there was any resentment, it had long since dissipated. When Lillard returned to Portland to play his first game in a visiting uniform that same month, he was greeted with multiple videos and a standing ovation.

I see a day where I will be back in the Trail Blazer uniform before I’m done.
Damian Lillard

Meanwhile, I was struggling to adapt to a new city and a new team.

In his first season in Milwaukee, he was an All-Star, averaging 24.3 points and 7.0 assists per game, but his chemistry with Giannis Antetokounmpo did not develop naturally on the court.

He never had the opportunity to play like he has in the first 12 years of his career. He played to win in the system he was in.
Aaron Goodwin

In their second season, Lillard and Antetokounmpo became the threat that the Bucks, and most NBA commentators, had envisioned when making the deal to bring them together. They were the highest-scoring duo in the NBA. The Bucks returned to Portland on January 28, 2025, for Lillard’s second home game. Before the start, Lillard made a point of greeting several Blazers executives, including Cronin, President Jody Allen, and Vice President Bert Kolde.

Nobody knew that two months later, Lillard would be diagnosed with deep vein thrombosis in his right calf, which would end his regular season. Or that four weeks later, he would tear his left Achilles tendon, likely ending his 2025-2026 campaign.

Or that the Bucks would surprise the NBA world by renouncing the nine-time All-Star, setting the stage for one of the most dramatic reunions in NBA history. The Bucks’ offseason could have taken different paths if Lillard had stayed healthy, from making minor adjustments to the roster to adding a new starting center to complement the growing relationship between Lillard and Antetokounmpo, or potentially trading Lillard. That was a last resort strategy, according to a source, that the team could have explored in an effort to find another star to pair with Antetokounmpo. However, Lillard’s new recovery time changed Milwaukee’s offseason plans. With Antetokounmpo in his prime, the Bucks were looking for ways to improve their roster. When the opportunity to sign Indiana’s center Myles Turner presented itself, Milwaukee made the move. It took the unprecedented step of waiving Lillard and extending the remaining $113 million of his contract. Lillard played 131 games in two seasons in Milwaukee. He averaged 24.6 points, 7.0 assists, and 43% shooting. The Bucks didn’t win any playoff series.

When you talk about winning a championship, it takes time to win a championship. It takes time to build and work together. I don’t think they had time for that.
Source not revealed

As soon as Lillard became the most unlikely free agent, the Blazers made their interest known. Cronin went to meet with Lillard at his home in Portland, to see the franchise icon surrounded by his family, to see how he was, both mentally and physically, with the rehabilitation of his torn Achilles tendon. While they were talking, each presented their respective vision for the future of the team.

It wasn’t a long conversation to get over that, and that was because we never had a bad relationship or there was never an aversion.
Damian Lillard

Lillard highlighted the basketball reasons why he was ready to believe in the Blazers again, from playing with young talents like Scoot Henderson to seeing the team acquire a veteran like Jrue Holiday. On July 17, the agreement was announced. WHEN LILLARD entered the room for his introductory press conference, the progress he had made in his recovery was evident. There was no walking boot in sight and the obvious question was asked. What are the chances you’ll play this season? It had only been three months since his Achilles tendon tear. A smile appeared on Lillard’s face, and he tried to look down to hide himself. Cronin also paused, the two exchanged a look of complicity. Together, they smiled and laughed. The truth is that neither side has any incentive to rush a return. The Blazers own their 2026 first-round pick in what is scheduled to be a strong and high-quality draft. And Lillard wanted a three-year contract to give him the flexibility to spend the entire ’25-26 season recovering if necessary, still giving him the ’26-27 season before his own player option in 2027. The deal also gives Lillard a no-trade clause. Meanwhile, Lillard said he has spent time shooting with one leg and shooting while sitting and considers himself ahead of schedule. He acknowledged how a younger version of himself would be determined to play again this season. But he also knows that the NBA’s actuarial tables are against him, and that that younger impulse could ultimately do more harm than good.

Obviously, it’s a difficult injury, but I know how I’m going to approach the whole rehabilitation process, taking my time. I think I’m going to get back to my form.
Damian Lillard

That mindset is what has driven Lillard to become one of the 75 best players in NBA history. But it’s also increasingly unlikely for a player of his age and with his role. “The most important thing for him will be the mental obstacle,” said a coach from the Eastern Conference. “He may have to overcome not being the primary ball handler.” “He may need to play a role like Mike Conley’s,” said another Eastern Conference executive. “Letting someone else bring the ball up and then being a secondary creator and a veteran on the court. It’s something difficult to overcome mentally.” Lillard said he has consulted with other NBA players who have torn their Achilles tendon, including Kevin Durant and Rudy Gay, but also NFL quarterback Aaron Rodgers. Those conversations, he said, combined with the consultations he has had with physical therapists and doctors, give him confidence that he can return to an All-Star level.

It’s Dame. I know Dame. I know the desire. I know the struggle. I know how hard he works. And I didn’t see this as something that was going to end his career. It’s going to be something that might even prolong his career because he works so hard that he has to give his body a break.
Aaron Goodwin

The way Durant recovered from a torn Achilles tendon in 2019, despite missing the entire 2019-20 season, gave a Western Conference executive the confidence that Lillard could still be effective. “Dame is a smart, high-IQ, elite offensive player like KD,” he said. “They’re going to be able to do that at a high level for a long time.” However, he offered another comparison, this one with a notable caveat: Dominique Wilkins ruptured his Achilles tendon in 1992 and returned to make two All-Star teams. Wilkins was able to return in 10 months, play 71 games the following season, and finish fifth in the 1993 MVP voting. Wilkins was 32 years old when he suffered the injury. “Lillard’s biggest challenge is that he will be several years older than all the best comparisons for someone who has recovered from this,” said the executive from the West. The Blazers have some time this season to predict that. Lillard too. For now, he’s back home, comfortable. He will spend the next phase of his recovery rebuilding strength in his left leg, working to identify ways to defy the long odds.