Lillard defeated Devin Booker 29-27 in the final round of the Three-Point Contest, claiming his third title in four years and joining Larry Bird and Craig Hodges as the only three-time winners in the competition's history. It was a reminder that one of the greatest shooting talents of his generation had not simply disappeared during his recovery.
Of course, knocking down uncontested shots is very different from navigating NBA defences, absorbing contact and keeping up with the physical demands of an 82-game season. But Lillard has since taken another step forward, returning to competitive action during the Portland Trail Blazers' preseason preparations and offering an early glimpse of how he might fit into the team's new-look backcourt.
Now back with the franchise where he spent the first 11 seasons of his career, Lillard faces a different challenge. The question is no longer whether he can still shoot. It is how much of the player who once defined Rip City remains - and what he can bring to a team that has changed considerably in his absence.
The making of Dame Time
Lillard's connection with Portland began on June 28th, 2012, when the Trail Blazers selected the Weber State guard with the sixth overall pick in the NBA Draft. Four months later, he made his NBA debut against the Los Angeles Lakers, facing a team led by Kobe Bryant, one of the players he had admired growing up.
There was little sign of rookie nerves. Lillard finished with 23 points and 11 assists in a 116-106 victory, becoming just the third player at the time to record at least 20 points and 10 assists in his first NBA game, joining Oscar Robertson and Allen Iverson.
He followed that performance with a remarkable rookie season, averaging 19.0 points and 6.5 assists while leading all first-year players in both categories. His consistency earned him the 2012/13 Rookie of the Year award by unanimous vote, making him only the fourth player in league history at the time to receive that honour.
What followed was more than a successful individual career. Over 11 seasons, Lillard became the face of the Trail Blazers, the franchise's all-time leading scorer and one of the most recognisable figures in Portland sports. His relationship with the city extended beyond basketball, and the loyalty he showed during years when championship contention remained out of reach helped strengthen that connection.
But if there is one quality that defined his time in Portland, it was his ability to deliver when the stakes were highest.
His series-winning three-pointer against the Houston Rockets in the 2014 playoffs provided an early glimpse of what was to come. Five years later, he produced a moment that would become inseparable from his name.
With Game 5 of Portland's 2019 first-round series against the Oklahoma City Thunder tied at 115, Lillard calmly dribbled near midcourt as the final seconds disappeared. Paul George defended him, but rather than driving toward the basket, Lillard stepped back and launched a three-pointer from approximately 37 feet.
The ball went through the net as time expired.
Portland won 118-115, eliminated the Thunder in five games and watched Lillard finish with 50 points and 10 three-pointers. His casual goodbye wave toward Oklahoma City's bench only made the moment more memorable. George later described the attempt as a bad shot, but for Lillard, that kind of range had become part of his game.
It was Dame Time in its purest form: confidence, extraordinary shooting ability and a willingness to take responsibility for the outcome.
And his scoring brilliance was not limited to the final seconds of close games. On February 26th, 2023, Lillard delivered one of the greatest individual performances in franchise history, scoring 71 points and making 13 three-pointers against the Rockets. He had already scored 41 by halftime and finished the game in fewer than 40 minutes.
At 32, he became the oldest player in NBA history to score at least 70 points in a regular-season game, adding another remarkable achievement to a career already filled with them.
The ring that never came
Yet despite the records, All-Star appearances and unforgettable playoff moments, one accomplishment remained missing.
After 11 seasons in Portland, Lillard was traded to the Milwaukee Bucks in September 2023, joining Giannis Antetokounmpo in pursuit of his first NBA championship.
The decision marked the end of an era for the Trail Blazers. Lillard had become synonymous with the franchise, but at 33, he wanted the opportunity to compete for a title while still playing at an elite level. Milwaukee, with an established superstar and championship experience, appeared to offer exactly that.
The partnership, however, never delivered the postseason success either side had envisioned.
During Lillard's first season with the Bucks, Antetokounmpo suffered a left calf injury shortly before the playoffs and missed Milwaukee's entire first-round series against the Indiana Pacers. Lillard also dealt with injuries, and the Bucks were eliminated in six games.
The following season brought an even more difficult ending. After missing time while receiving treatment for a blood clot in his right calf, Lillard returned for the playoffs, only to suffer a torn left Achilles tendon during Game 4 against the Pacers on April 27th, 2025. Milwaukee lost the series 4-1, leaving the team's much-anticipated partnership without a single playoff series victory.
Just over two months later, the Bucks made another surprising decision. They waived Lillard and stretched approximately $112.6 million in remaining guaranteed salary over five seasons, creating room for the arrival of Myles Turner. The decision was financially significant and marked an unexpected end to Lillard's pursuit of a championship in Milwaukee.
But what initially looked like another major setback soon opened an unexpected door.
In July 2025, Lillard agreed to return to Portland on a three-year contract. He would spend the following season recovering from his Achilles injury, but the destination of his comeback was already decided.
After leaving Rip City in search of a championship, he was coming home without the ring he had hoped to win.
A familiar city, a different team
The Portland Trail Blazers Lillard is returning to are not the same team he left in 2023.
Last season, Portland finished 42-40 and returned to the playoffs, showing significant progress after several years of rebuilding. The franchise now has a younger core, greater depth and ambitions that extend beyond simply developing talent.
For Lillard, that creates an interesting situation. He is no longer being asked to carry an entire offence, but finding his place in an increasingly crowded rotation could be one of the biggest challenges of his comeback.
Deni Avdija has emerged as a central figure in Portland's attack. Coming off his first All-Star season, during which he averaged a career-high 24.2 points per game, the Israeli forward has developed into a versatile scorer and playmaker capable of creating opportunities for himself and his teammates.
The arrival of Ja Morant adds another dimension. Few guards can match Morant's explosiveness when attacking the basket, and his ability to collapse defences could create valuable opportunities for Lillard on the perimeter. At the same time, Morant is accustomed to controlling the offence, meaning the two will need to find a balance between handling the ball and playing off it.
That is where Lillard's shooting could become particularly important.
Even if he no longer possesses the same burst he had earlier in his career, defenders cannot afford to ignore him beyond the three-point line. His ability to stretch the floor could provide more room for Morant's drives and Avdija's attacks, while his experience running pick-and-roll situations offers Portland another way to generate offence when its initial options break down.
Donovan Clingan could be another beneficiary. The young centre led the NBA with 4.5 offensive rebounds per game last season, giving Portland a significant advantage on the glass. His size and screening ability also make him a potentially useful partner for Lillard, whose success in the pick-and-roll has long been a defining part of his offensive game.
The Blazers have important defensive pieces as well. Toumani Camara brings physicality and the ability to challenge opposing perimeter players, while two-time NBA champion Jrue Holiday provides experience, defensive versatility and leadership. Scoot Henderson remains another talented young guard looking to establish himself, although Shaedon Sharpe's knee injury complicates the team's backcourt rotation.
Managing those different pieces will be a major task for new head coach Micah Nori.
Portland have plenty of players capable of handling the ball, but that does not automatically translate into an efficient offence. Lillard, Morant and Avdija all have experience as primary creators, and determining who initiates possessions, who plays off the ball and which combinations work best could take time.
There are also legitimate concerns about Lillard's physical condition. An Achilles rupture is a serious injury for any basketball player, particularly a guard whose game has relied on changes of pace, separation and the ability to create space against elite defenders.
His February shooting-contest victory demonstrated that his touch remains intact, but it could not answer questions about lateral movement, defensive mobility or the physical demands of a full NBA schedule. At 36, managing his minutes and workload will likely be just as important as finding his offensive role.
Before the injury, Lillard averaged 24.9 points and 7.1 assists in his final season with Milwaukee. Those numbers reflect a player who remained an elite offensive threat well into his thirties. Portland may not need that version of him every night, but another reliable shot creator could make a difference in close games and against disciplined playoff defences.
Perhaps most importantly, Lillard brings something that cannot be measured entirely through statistics. He understands what it means to lead the Trail Blazers, to face the expectations of their fans and to perform under postseason pressure. For a roster with several young players still establishing themselves, that experience could prove valuable.
The challenge is finding a way to benefit from everything Lillard offers without slowing the development of the team around him.
One more Dame Time?
At 36, Lillard is no longer expected to carry Portland's offence or deliver 30-point performances on a nightly basis. With a talented young core around him, his role will be different, but that does not necessarily make it any less important.
The Trail Blazers have taken a step forward, but competing in the Western Conference remains a considerable challenge. If Lillard can stay healthy, provide reliable scoring and help Portland become a more dangerous playoff team, his return could prove valuable beyond the numbers on the stat sheet.
And while his first NBA championship ring remains out of reach, the possibility of winning it with the franchise where his career began adds another layer to the story.
Dame Time may not look exactly as it once did. But in Rip City, the clock has not stopped just yet.