In late July, over 400 enthusiastic children gathered at the YMCA in Beaverton, Oregon, for Damian Lillard`s annual basketball camp. For the past two years, this event had felt more like a brief, nostalgic visit than a regular engagement with a beloved local hero.
The most frequently asked question from the young campers was both poignant and predictable:
“When will you be returning home permanently?”
However, this year, that question was conspicuously absent.
Just a week earlier, news had surfaced that Lillard was signing a three-year contract to rejoin the Portland Trail Blazers, instantly transforming the camp into a joyful homecoming celebration.
The majority of attendees, aged between 6 and 16, proudly sported their Lillard jerseys – a mix of Milwaukee green and Portland`s distinctive rose. Lillard quipped to onlookers that he had spent more time answering questions about his return than demonstrating basketball skills.
Speaking at his reintroduction press conference in late July, Lillard remarked, “I likely wouldn`t have believed this would happen in just two years. While I always anticipated a return at some point, I certainly didn`t expect it to occur this quickly.”
His return culminated several days of enthusiastic celebration, highlighted by the team`s social media channels capturing his emotional first re-entry into the home locker room and seeing his personalized nameplate precisely where he had left it. He was visibly overwhelmed with happiness.
A source close to the situation revealed, “In all honesty, he never wished to depart.”
Lillard`s decision to return to Portland was significantly influenced by children – not only the adoring young participants at his 12th annual basketball camp but also the desire to spend more quality time with his own kids: 7-year-old Dame Jr. and his 4-year-old twins, Kali and Kalii.
Lillard recounted informing his children about his new Portland contract while stopped at a traffic light.
His daughter`s immediate response was, “No more flights to Milwaukee?”
At the reintroduction ceremony, positioned at a Blazers podium, Lillard sat alongside General Manager Joe Cronin and Coach Chauncey Billups. They fielded questions regarding his recent injury – a torn left Achilles suffered during Game 4 of the first round of the playoffs – his contentious departure from Portland, and the dynamics of both his former and current teams. Each individual`s responses consistently revolved around a deeply emotional theme, underscoring the purpose of their gathering in late July.
Cronin expressed, “Witnessing Damian in another team`s jersey simply never felt appropriate.”
Lillard, seated to Cronin`s left, echoed this sentiment.
He elaborated, “It always felt wrong not being back home. I never desired to play for any other organization. Being reunited with this community just feels entirely right.”
Sources indicate that Lillard consistently envisioned himself returning to Portland, even conveying to his inner circle his intention to retire as a Blazer before his trade to Milwaukee materialized.
Despite a devastating Achilles injury that will keep him off the court next season, compounded by a deep vein thrombosis diagnosis in his right calf just four weeks prior on March 25, Lillard remains confident he can guide the Blazers` promising young roster towards building a championship-caliber team in a city that hasn`t celebrated an NBA title since 1977.
The primary challenge, however, is that he will be 36 years old by the time he is able to rejoin the team on the court.
While his unexpected return to the Blazers stands as one of the most heartwarming narratives of the NBA offseason, a critical question persists: Following two challenging, injury-plagued seasons in Milwaukee, what will the remainder of Lillard`s career entail, particularly after his Achilles recovery?
The Unlikely Journey Back Home
During the 2023 summer free agency period, Lillard sought a trade from the sole franchise he had ever played for. His explicit preference was to join the then-Eastern Conference champions, the Miami Heat, to play alongside Jimmy Butler and Bam Adebayo.
The Blazers had recently concluded their season in 13th place in the Western Conference with a 33-49 record, marking their second consecutive year missing the playoffs. For an extended period, Lillard and his agent, Aaron Goodwin, had consistently implored the team to enhance its roster, a request that had largely gone unfulfilled.
By September, with no progress on a potential Miami trade, Lillard began training at the Blazers` facility and re-engaging with the team.
Sources indicated that Goodwin conveyed Lillard`s willingness to remain in Portland, but following months of speculation, the team aimed to resolve the trade request before training camp. With only a week left, Lillard was ultimately traded to Milwaukee.
Lillard attributed the situation primarily to “miscommunications and misunderstandings,” adding, “Joe and I never discussed a potential return. The idea simply lingered, and we allowed it to remain unresolved, which I now believe was a mistake.”
However, merely months after the trade, the groundwork for a potential reunion began to emerge.
In January, Goodwin and Cronin engaged in a discussion where they acknowledged past communication breakdowns and affirmed that any lingering ill will had long since vanished.
Later that month, upon Lillard`s return to Portland for his inaugural game in an opposing uniform, he was met with several commemorative video presentations and a heartfelt standing ovation.
At that time, Lillard stated, “I envision a future where I`ll once again wear a Trail Blazer uniform before my career concludes.”
Meanwhile, he was finding it difficult to adapt to life in an unfamiliar city and with a new team.
Despite his struggles, he earned an All-Star selection in his debut Milwaukee season, averaging 24.3 points and 7.0 assists. However, his on-court chemistry with Giannis Antetokounmpo did not develop organically.
Goodwin noted, “He never truly had the chance to play in the style he had established over the first 12 years of his career. He adapted his game to win within the system provided.”
By his second season, Lillard and Antetokounmpo had blossomed into the formidable duo the Bucks – and most NBA analysts – had anticipated when the trade was made. They emerged as the league`s highest-scoring pair.
On January 28, 2025, the Bucks visited Portland for Lillard`s second return game. Prior to tip-off, Lillard made a deliberate effort to greet several Blazers executives, including Cronin, Chairwoman Jody Allen, and Vice Chair Bert Kolde.
Unbeknownst to them, just two months later, Lillard would be diagnosed with deep vein thrombosis in his right calf, prematurely ending his regular season. Furthermore, four weeks after that, he would suffer a torn left Achilles, an injury likely to sideline him for the entire 2025-2026 season.
Even more surprisingly, the Bucks would then stun the NBA by waiving the nine-time All-Star, paving the way for one of the most remarkable reunions in league history.
Had Lillard remained healthy, the Bucks` offseason strategies might have varied considerably – from minor roster adjustments, such as adding a new starting center to enhance the developing synergy between Lillard and Antetokounmpo, to a potential trade of Lillard himself. A source indicated that the latter was considered a last-resort option to acquire another star to complement Antetokounmpo.
Nevertheless, Lillard`s extended recovery period fundamentally altered Milwaukee`s offseason strategy. With Antetokounmpo in his prime, the Bucks were actively seeking roster improvements. When the chance arose to sign center Myles Turner from Indiana, Milwaukee seized the opportunity, taking the extraordinary step of waiving Lillard and deferring the remaining $113 million on his contract over several years.
Over his two seasons in Milwaukee, Lillard participated in 131 games, averaging 24.6 points, 7.0 assists, and shooting 43% from the field. Notably, the Bucks failed to advance beyond the first round in either playoff appearance.
A source commented, “Achieving a championship requires time to build a cohesive unit and foster teamwork. I don`t believe they were afforded that necessary time.”
The moment Lillard unexpectedly became a free agent, the Blazers immediately expressed their interest.
Sources indicated that Cronin visited Lillard at his Portland residence, observing the franchise legend amidst his family, and inquiring about his mental and physical well-being during his Achilles rehabilitation. During their conversation, both men articulated their individual visions for the team`s future.
Lillard stated, “It didn`t take long to move past past issues, largely because our relationship was never truly negative, nor was there any personal animosity.”
Lillard emphasized the basketball-centric reasons for his renewed faith in the Blazers, citing the prospect of playing alongside burgeoning talents like Scoot Henderson and the team`s acquisition of a seasoned veteran such as Jrue Holiday.
The agreement was officially announced on July 17.
The Road Ahead: Recovery and Expectations
Upon Lillard`s entry into the room for his introductory press conference, the significant strides he had made in his recovery were immediately apparent. With no walking boot visible, the most pressing question was inevitably posed:
What is the likelihood of you playing this season?
Only three months had passed since his Achilles tear.
A faint smirk played on Lillard`s face as he attempted to conceal it by looking down. Cronin also paused, and the two shared a knowing glance before both smiled and chuckled.
In reality, neither party has an incentive to expedite his return. The Blazers hold their 2026 first-round pick, which is projected to be from a strong, talent-rich draft class.
Furthermore, Lillard sought a three-year contract to provide him the flexibility to dedicate the entire 2025-2026 season to recovery if needed, ensuring he would still have the 2026-2027 season before his player option in 2027. The agreement also includes a no-trade clause for Lillard.
Currently, Lillard stated he has been practicing shooting on one leg and from a seated position, believing he is ahead of his rehabilitation schedule. He admitted that a younger version of himself would be eager to rush back this season. However, he also recognizes that the statistical probabilities in the NBA are not in his favor for a quick return, and that impulsive desire could ultimately cause more harm than good.
Lillard asserted, “It`s clearly a challenging injury, but I understand my approach to the rehabilitation process: taking my time. I believe I will regain my previous form.” This determined mindset has been instrumental in Lillard`s rise to becoming one of the NBA`s top 75 players. However, achieving this at his age and given his expected role is becoming increasingly improbable.
An Eastern Conference coach remarked, “His greatest challenge will be mental. He`s accustomed to playing a certain way throughout his career, but he might need to adapt to not being the primary ball-handler.”
Another Eastern Conference executive suggested, “He might need to adopt a role similar to Mike Conley in Minnesota – allowing someone else to initiate the offense and then serving as a secondary playmaker and veteran presence on the court. That`s a difficult mental adjustment.”
Lillard shared that he has sought advice from other athletes who have suffered Achilles tears, including NBA players Kevin Durant and Rudy Gay, as well as NFL quarterback Aaron Rodgers. He stated that these discussions, along with consultations with physical therapists and doctors, bolster his confidence in returning to an All-Star caliber performance.
Goodwin asserted, “It`s Dame. I know Dame. I understand his drive, his resilience, and his work ethic. I never viewed this injury as something that would end his career. Instead, I believe it might even extend it, as his intense dedication often necessitates his body getting a much-needed break.”
One Western Conference executive expressed confidence in Lillard`s continued effectiveness, citing Kevin Durant`s successful recovery from a torn Achilles in 2019, despite missing the entire 2019-2020 season. He commented, “Dame is a smart, high-IQ, elite offensive player, much like KD. They possess the ability to perform at a high level for an extended period.”
However, he presented another comparison, though with a crucial distinction: Dominique Wilkins, who tore his Achilles in 1992, subsequently returned to earn two All-Star selections. Wilkins recovered within 10 months, played 71 games the subsequent season, and finished fifth in the 1993 MVP voting.
Wilkins was 32 years old at the time of his injury.
The Western executive concluded, “Lillard`s most significant hurdle is that he will be considerably older than the top comparable players who have successfully recovered from this type of injury.”
The Blazers have this season to assess the situation and plan accordingly. Lillard also has this time for his own preparations.
Currently, he is back home and at ease. He will dedicate the next stage of his recovery to regaining strength in his left leg, striving to find methods to overcome the formidable challenges ahead.
Lillard affirmed, “I`m dedicating the entire next season to ticking every box and ensuring I don`t rush my return.”
He then reiterated his commitment.
“I anticipate returning to my peak performance level.”