Rose City recovery: What’s next for Damian Lillard’s NBA career in Portland

MORE THAN 400 children packed into a gymnasium at the YMCA in Beaverton, Oregon, in late July for an annual basketball camp. The Damian Lillard Basketball Camp had continued in Oregon, but for the past two years it felt more like a fleeting reunion than a yearly visit with a hometown star.

The most popular question from campers was as heartbreaking as it was obvious.

“So, when are you coming home?”

No such inquiry was required this session.

News broke a week prior that Lillard was signing a three-year deal to return to the Portland Trail Blazers, transforming the camp into the happiest of welcome back parties.

Most of the campers, ages 6 to 16, wore their Lillard jerseys — an assortment of Milwaukee green and Portland rose — and Lillard joked to those around him that he had fielded more questions about his return than basketball drills.

“In just two years, I probably wouldn’t have believed it,” Lillard said in late July at his introductory press conference. “I’d be lying if I said I didn’t expect this to happen at some point, but for it to happen this soon, I wasn’t expecting this.”

It was the culmination of days of fanfare surrounding Lillard’s return, including the team’s social media team capturing Lillard’s first return back into the home locker room, and seeing his placard for the first time, right where he left it. He was overcome with joy.

“Truthfully, he never wanted to leave,” a source told ESPN.

Kids brought Lillard back to Portland, not just the gaggle of them at his 12th annual basketball camp that adores him, but a chance to spend more time with his own: Dame Jr., 7, and four-year-old twins, Kali and Kalii.

Lillard said he told his children about his new contract with Portland at a local traffic light.

His daughter replied: “No more flights to Milwaukee?”

In front of a Blazers lectern at his reintroduction ceremony, Lillard sat with general manager Joe Cronin and coach Chauncey Billups, answering questions about his injury — he tore his left Achilles during Game 4 in the first round of the playoffs — about his acrimonious exit from Portland, about his old and new team. Each answer, from each man, centered around a sentimental theme — and the reason why they all gathered on that TK day in late July.

“It never felt right seeing Damian in a different jersey,” Cronin said.

Lillard, sitting to Cronin’s left, said the same.

“It never felt right, not being home,” he said. “I never wanted to not be playing for this organization. To be back in this community, it all just feels right.”

Lillard always saw himself back in Portland, sources said, telling people close to him that he planned to end his career with the Blazers even before he was traded to Milwaukee.

Even with a catastrophic injury that will sideline him next season, on top of another one he had suffered just four weeks before — he was diagnosed with deep vein thrombosis in his right calf on March 25 — he believes he can help the Blazers’ young talent start to build a winner in a city that hasn’t seen a champion since 1977.

The one catch? He will be 36 years old when he can join them.

His unlikely return to the Blazers is one of the feel-good stories of the NBA offseason, but a central question remains: After two frustrating, injury-filled seasons in Milwaukee, what will the post-Achilles portion of Lillard’s career look like?

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AS FREE AGENCY opened up during summer 2023, Lillard requested a trade from the only franchise he had ever known. And Lillard specifically wanted to join the then-Eastern Conference champion Miami Heat to team up with Jimmy Butler and Bam Adebayo.

The Blazers had just finished 13th in the West at 33-49, missing the playoffs for the second consecutive season. For years, Lillard and his agent, Aaron Goodwin, had urged the team to upgrade the roster. And for years the team failed.

By September, with no signs of a Miami deal, Lillard began working out at the Blazers’ facility and reintegrating himself with the team.

Goodwin communicated to the Blazers that Lillard would stay in Portland, but after months of speculation, the team wanted to resolve the request by training camp, sources told ESPN. With a week to go, Lillard was traded to Milwaukee.

“More than anything, it was miscommunications and misunderstandings,” Lillard said. “Joe and I never talked about [a potential return]. It just sat out there and we let it be what it was, I think that was the mistake.”

But just a few months after the trade, steps toward a potential reunion in the future started to take shape.

Goodwin and Cronin had a conversation in January, where they identified the gaps in their communication and said that if there were any hard feelings, they had long since dissipated.

When Lillard returned to Portland to play his first game in a visiting uniform later that month, he was greeted with multiple video packages and a standing ovation.

“I see a day where I’ll be in a Trail Blazer uniform again before I’m done,” Lillard said then.

In the meantime, he was struggling to adjust to life in a new city and a new team.

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

“He never really had an opportunity to play as he has played the first 12 years of his career,” Goodwin told ESPN. “He played to win in the system that he was in.”

In his second season, Lillard and Antetokounmpo became the kind of threat the Bucks — and most of the NBA commentariat — envisioned when they made the deal to team them up. They were the highest-scoring duo in the NBA.

The Bucks returned to Portland on Jan. 28, 2025, for Lillard’s second game back home. Before tipoff, Lillard made it a point to greet various Blazers executives, including Cronin, chairwoman Jody Allen and vice chair Bert Kolde.

Little did any of them know that two months later, Lillard would be diagnosed with deep vein thrombosis in his right calf, ending his regular season. Or that four weeks after that, he would tear his left Achilles, likely ending his 2025-2026 campaign.

Or that the Bucks would shock the NBA world and waive the nine-time All-Star, setting the stage for one of the most dramatic reunions in NBA history.

The Bucks offseason could have taken a few different paths had Lillard stayed healthy — from tinkering around the margins of the roster to add a new starting center to complement a growing relationship between Lillard and Antetokounmpo or potentially trading Lillard, a last-ditch strategy, a source told ESPN, the team could have explored in 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 on the prowl for ways to improve their roster. When the opportunity to sign center Myles Turner away from Indiana presented itself, Milwaukee decided it could not afford to waste a year of Antetokounmpo’s prime, TK attribution. They took the unprecedented measure to waive Lillard and stretch the $113 million remaining on his contract.

Lillard played 131 games in two seasons in Milwaukee. He averaged 24.6 points, 7.0 assists and shot 43%. The Bucks did not win a single playoff series.

“When you talk about winning a championship, it takes time to win a championship,” a source told ESPN. “It takes time to build and work together. I don’t think they had time to do that.”

As soon as Lillard became the unlikeliest of free agents, the Blazers made their interest known.

Cronin went to meet Lillard at his Portland home, sources told ESPN, to see the franchise icon surrounded by his family, to check on how he was doing, both mentally and physically with the rehab of his torn Achilles. As they talked, they each presented their respective vision for the team’s future.

“It wasn’t a long conversation to move past that, and that was because we never had a bad relationship or it was never a dislike,” Lillard said.

Lillard highlighted the basketball reasons he was ready to believe in the Blazers again, from playing with young talent like Scoot Henderson to seeing the team acquire a veteran like Jrue Holiday.

On July 17, the deal was announced.

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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 play this season?

It had been just three months since his Achilles tear.

A smirk crept across Lillard’s face, and he tried to look down to hide. Cronin paused too, the two exchanging a knowing glance. Together, they smiled and laughed.

The truth is neither side has any incentive to rush a comeback. The Blazers own their 2026 first-round pick in what is slated to be a strong, top-heavy draft.

And Lillard wanted a three-year deal 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.

In the meantime, Lillard said he has passed time shooting on one leg and shooting sitting down and considers himself ahead of schedule. He acknowledged how a younger version of himself would be intent on rushing back to play this season. But he also knows the NBA actuarial tables are working against him — and that that younger impulse might ultimately damage more than expedite.

“It’s obviously a tough injury, but I know how I’m going to approach the whole rehab process, taking my time,” Lillard said. “I think I’m going to return to form.” That mindset is what has driven Lillard to become a top 75 player in NBA history. But it’s also increasingly unlikely for a player his age, and with his role.

“The biggest thing for him will be the mental hurdle,” one Eastern Conference coach told ESPN. “He’s been used to doing it one way his whole career, but he may have to get over not being the primary ball handler.”

“He may need to play a role like [Minnesota’s] Mike Conley,” another Eastern Conference executive told ESPN. “Let someone else bring the ball up and then be a secondary creator and vet on the floor. It’s a tough thing to get over mentally.”

Lillard said he has consulted other players who have torn their Achilles, like Kevin Durant and Rudy Gay, but also NFL quarterback Aaron Rodgers. Those conversations, he says, combined with the consultations he has had with physical therapists and doctors, give him confidence he can return to All-Star level.

“It’s Dame. I know Dame,” Goodwin told ESPN. “I know the desire. I know the fight. I know how hard he works. And I didn’t see this as anything that was going to shut down his career. It’s going to be something that was going to maybe even prolong his career because he goes so hard that he’s got to give his body a break.”

The way Durant has bounced back from a torn Achilles in 2019, despite missing the entire 2019-20 season, gave one Western Conference executive confidence Lillard could still be effective. “Dame’s 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 noted caveat: Dominique Wilkins ruptured his Achilles 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 vote.

Wilkins was 32 when he suffered the injury.

“Lillard’s biggest challenge is that he will be several years older than all the best comps for someone who’s come back from this,” the West exec said.

The Blazers have some time this season to forecast that. Lillard does too.

For now, he’s back home, comfortable. He’ll spend the next phase of his recovery rebuilding strength in his left leg, working to identify ways to defy the long odds.

“I’m taking next season to check every box and make sure I don’t rush,” Lillard said.

Then he repeated himself.

“I expect to return to form.”