The Portland Trail Blazers reside in an NBA landscape that often deals in absolutes: Teams are either contending or rebuilding. This black-and-white world doesn’t always know how to make sense of a team like the Trail Blazers — one that is working toward the middle stages of that journey — or how to discern the value a decorated 35-year-old guard like Jrue Holiday can bring to a team navigating the in-between.
Throughout Holiday’s 14-minute introductory media session Tuesday in Tualatin, the two-time
NBA champion provided varied answers to that last question.
“To be me,” he said about the expectations Portland head coach Chauncey Billups has for him next season. “To bring the leadership that I’ve brought to multiple organizations. To be able to come in here and be as adaptable as possible. And again, the most important thing is to win.”
As Holiday mentioned, winning is a primary reason why Portland acquired him. Still, the Blazers dealing Anfernee Simons to the Boston Celtics for Holiday in their only offseason trade wasn’t a win-now move as it’s often been described. That phrase doesn’t quite capture the right connotation of Portland’s situation. Instead, the Holiday acquisition is a win-more move. The Blazers aren’t on the verge of a title push like the last two teams who traded for Holiday, but they are ready to take the next steps and push toward their first winning record and postseason berth since 2021.
“If it’s getting to the playoffs, if it’s winning a championship,” Holiday said, “I feel like winning is the purpose and the reason why I’m here.”
For a team with designs of moving upward, Holiday is an ideal hire for the mission. He joins the Blazers with an elite résumé of accolades built up over his 16-year career (three All-Defensive First Team selections, three All-Defensive Second Team selections, two All-Star selections, two championships, two Olympic gold medals). The veteran also carries a track record of being one of the league’s premier fixer-uppers. The Milwaukee Bucks acquired Holiday in the 2020 offseason, and he played a crucial role in their title run the following spring. Then the Celtics traded for Holiday in the 2023 offseason and again a championship parade followed.
Holiday’s style of play — headlined by defense, adaptability and veteran know-how — projects as a symbiotic addition to the Blazers’ core foundation. All of those attributes translate to Portland’s goals next season to win more games, continue the cohesion and momentum of its newfound defensive identity, and cultivate a competitive ecosystem for its young players to develop in on and off the court.
It’s unclear at this moment who will start among the Blazers backcourt of Holiday, Scoot Henderson and Shaedon Sharpe. Holiday wasn’t directly asked about if he prefers to start, but he said he’ll fit in wherever when discussing his expected role. Regardless of where the three guards land on the depth chart, Holiday should complement Portland’s young guards better than the outgoing Simons, who worked best in a ball-dominant role that clashed with Henderson’s style and usage.
In contrast, Holiday can handle point guard duties alongside Sharpe, but also slot in as a 3-and-D wing or secondary creator alongside Henderson. He has that size and skill at 6-foot-4 with a career shooting stroke of 37% from beyond the arc.
“I’m a complete basketball player, so you can’t just put one position on me,” Holiday said Tuesday. “ ... I feel like I’m a good fit with anyone.”
The shift to Holiday should clarify roles on Portland’s roster, while adding an upgrade to the Blazers’ improving defense. At 35, Holiday is coming off a down season where he didn’t land on either All-Defensive Team for the first time in five years. But even if he doesn’t get back to peak form, he still provides Portland with another skilled point-of-attack defender who can hound opposing point guards on the perimeter — a new weapon that comes with unparalleled experience.
“Hopefully, just knowledge,” Holiday said about what he brings that’ll help the defense. “Maybe [there’s] something that I’ve seen that the young guys haven’t seen yet or just coming in with that same type of energy at the point guard position, guarding the point guard. Sometimes being the head of the snake in that way could lead to a strong defense behind you.”
That point about knowledge speaks to the mentorship aspect of the acquisition, which was a hot topic at Holiday’s media session. The questions about the subject are only natural considering Holiday is now the oldest player on one of the NBA’s youngest teams, beating out friend and new teammate Damian Lillard by 33 days. Billups had talked last season about how the Blazers rostered several players with quieter, laid-back personalities. Heading into next season, the franchise has balanced the roster alchemy more by acquiring Holiday and Lillard in the same month, two of the most heralded leaders in the sport.
In terms of professionalism and team chemistry, Holiday’s résumé speaks for itself again. He’s a three-time winner of the NBA’s Twyman-Stokes Teammate of the Year Award, a two-time winner of the NBA Sportsmanship Award and the 2025 winner of the NBA Social Justice Champion Award.
In his answers Tuesday, Holiday understood he’s partly here to help guide Portland’s young players along on their NBA journeys. Looking back at the beginning of his own career with the Philadelphia 76ers, he understood the value of his own mentors. He said Andre Iguodala, Elton Brand and assistant coach Aaron McKie taught him lessons about consistency, work ethic, and how being solid as a human translates on and off the court.
“Sometimes as a young kid, you might not lock in as much as you probably should,” Holiday said. “Obviously, you have creativity. You might want to try things if it’s defensively or offensively. And [Iguodala] would always tell me, ‘just be solid.’ So he would give me hints on when to pick and choose to be creative and when to take risks.”
The presence of Holiday should benefit Henderson. The 21-year-old guard is entering a pivotal third season after an up-and-down start to his career, the ebbs and flows magnified by the colossal hype that accompanies a No. 3 overall pick. Holiday was complimentary of Henderson’s game, mentioning his aggression and improved shooting. While discussing how they’ll fit together, Holiday said he wants to help put the guard in a position to succeed this upcoming season.
“Just being able to play off him knowing that Scoot is the next one up and to be able to go out here and really just showcase what he can do,” he said.
That perspective requires a selfless and professional attitude. Those attributes are often required for high-level veterans joining a team not considered a contender, especially for a competitor like Holiday who won titles at his last two stops. From where the Blazers stand in the pecking order, building toward a championship is still likely a years-long exercise in delayed gratification. Holiday is helping his new teammates and franchise work toward that goal, with no guarantee that he’ll be around to bask in the payoff.
Transitioning from a contender to a team fighting to make the playoffs isn’t always the easiest job, Holiday said, but he’s on board, and he’s here to make an impact.
“I’ve been in the game long enough to know that it’s not always gonna be the brightest or the best or the easiest, whatever you want to say,” he said. “But I think coming to a team and an organization that has the character of this team and organization makes basketball great. That’s why you want to come here and you want to play because you feel like you’re a part of something bigger than yourself. You feel like you’re a part of a bigger team and a bigger purpose.”
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