Portland Trail Blazers fans have been on high since the homecoming of Damian Lillard. After a brief stint in Milwaukee, their prodigal star has returned. But aside from that, Tim Bontemps is confused about their offseason strategy. Particularly, why did they help the Celtics and take on an aging Jrue Holiday?
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The two-time champion has $104 million owed over the next three years. Bontemps finds it hard to see his value on a young Trail Blazers team. “It’s like, OK, you add Drew Holliday to this team, but where does he fit? And why are you doing this?” he questioned. His co-host, Tim MacMahon, was quick to fill him in. He sees Holiday play a role similar to Fred VanVleet on the Houston Rockets.
“He[VanVleet] was worth every penny of that because of him helping to establish the culture and the leadership and the toughness and the professionalism and all those kind of things. I got to think that’s part of the vision and the hope with Drew Holliday in Portland. I will say, as consummate of a pro as he is, I’ve never heard anything but great things about Jrue Holliday’s character,” MacMahon explained on Hoop Collective.
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The Rockets felt agony as VanVleet tore his ACL right before training camp. His impact goes beyond stats. VanVleet brought direction and grit to the Rockets. Jrue Holiday is a 17-year pro with a reputation of being the “finishing piece”. In his first years with both the Bucks and the Celtics, the 35-year-old helped deliver championships.

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Mar 15, 2025; Brooklyn, New York, USA; Boston Celtics guard Jrue Holiday (4) reacts after making a three point shot ]against the Brooklyn Nets during the second half at Barclays Center. Mandatory Credit: John Jones-Imagn Images
The Trail Blazers are, of course, far from competing in the West. But they have promising stars in Shaedon Sharpe and Scoot Henderson, who will benefit the most from having Lillard and Holiday around them every day. For a team with a young nucleus, a few veterans could accelerate their development.
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However, there’s a key difference between Fred VanVleet and Holiday. “Fred VanVleet chose to go to Houston,” MacMahon noted. Holiday didn’t, which is part of why a narrative is being built.
Why Jrue Holiday could overturn the ‘worst move’ narrative
In a recent survey, league insiders voted the Trail Blazers’ deal for Holiday as the worst offseason move. The reasons are visible. They have a logjam of guards, and Holiday only adds to the troubles of managing their minutes. But this isn’t like the last time he was traded to the Blazers. This time, Holiday sees his value.
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In a candid discussion, he revealed his excitement about joining the Blazers. “The goal is to win and to make some noise. I think that after the last few years of what has happened after Damian Lillard being traded — and then now Dame’s back — I think it’s an exciting time here in Portland. It’s an exciting time to be a Trail Blazer, and I’m excited to be part of it,” he said.
At a later stage of his career, Holiday might have a reserved role if he spends more than one season with Portland. But this year, his on-court ferocity is essential. Without Lillard’s scoring, the Trail Blazers will likely rely on Sharpe and Scoot to create. But Holiday, even at 35, is their best on-ball defender.
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The team might not be spoken about enough. But last season they ended with 36 wins, and have now added some depth to their lineup. Holiday allows Chauncey Billups to experiment with his resources and potentially take the Western Conference by surprise. Currently, the two-time champion is thrilled to work with the young team.
Can he be the finishing piece for the third time in his career? If not that, Jrue Holiday can contribute positively to this unsolved puzzle.
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