“That’s why you want to come here and you want to play because you feel like you’re a part of something that’s bigger than yourself.”
Jrue Holiday was traded by the Celtics in late June. (AP Photo/Michael Dwyer, File)
Jrue Holiday’s tenure with the Trail Blazers has come full circle … in a way.
Holiday’s trade from Boston to Portland last month marks the second time that the two-time NBA champion has landed with the Blazers.
Granted, his first stint with the Trail Blazers only lasted a few days — as he was flipped from Milwaukee to Portland in September 2023 before the Celtics acquired him as part of a blockbuster move that solidified the franchise’s 18th title.
This time around, the 35-year-old guard expects to be staying put with Portland to help elevate a young roster on the rise. Speaking for the first time since his trade from Boston, Holiday elaborated on some of the emotions drawn out of last month’s trade and his two-year run with the Celtics.
“I was at home in California,” Holiday told reporters in Portland on Tuesday. “I ended up getting a call from Brad [Stevens] and he ended up telling me a little bit before. But I was excited. I knew that obviously I got traded here before. So it was just kind of full circle. Talking to [Portland coach] Chauncey [Billups] about it. Talking to [Portland GM] Joe [Cronin] about it.
I really do appreciate what they did for me the first time around. That really does mean a lot for me in my career. So I know this time around, just talking to them, they’re just kind of like, I got another chance to get you and they thought that I’d be a good piece here.”
Even though Holiday is not necessarily expected to be the final piece needed for Portland to assert themselves as contenders — much as he was in Boston — the defensive stalwart believes that the Trail Blazers can take a major step forward in 2025-26.
Not only did Portland’s young core end last season on a high note with a winning record over the last two months, but their roster should receive another lift in 2026-27 when Blazers great Damian Lillard — who re-signed with Portland in free agency — is expected to rejoin the team after recovering from a torn Achilles.
“I’ve been in the game long enough to know that it’s not always going to be the brightest or the best or the easiest, whatever you want to say,” Holiday said. “But I think coming into a team and 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 that’s bigger than yourself.”
Holiday’s departure from Boston felt all but inevitable this offseason, given the four-year, $135 contract extension that he signed in April 2024 and Boston’s need to cut payroll this summer in order to get under the NBA’s restrictive second apron.
Still, Brad Stevens noted earlier this month that the Celtics’ cost-cutting measures — while expected — stung all the same for a team that was seemingly in the midst of a sustained contention window just a few months ago.
“Jrue Holiday is — I think he stamped his Hall-of-Fame candidacy here, if he didn’t already have it,” Stevens said. “And we’ll look forward to watching and rooting and following him from afar. But he’s as good of a person as you could ever have in your building and as part of your team.”
“I actually talked to both those guys a couple weeks before and just said, ‘Listen, there’s a chance that you’re back, but there’s also a high chance that you’re not,’” Stevens added of his conversations with Holiday and another traded Celtic in Kristaps Porzingis. “And the agents have done a good job of understanding the challenges of the new CBA and the second aprons, and it was really important for us to get us out of that penalty box in a lot of ways, because you can feel those, and those are real things.”
Conor Ryan is a staff writer covering the Bruins, Celtics, Patriots, and Red Sox for Boston.com, a role he has held since 2023.
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