The Trail Blazers introduced Jrue Holiday on Tuesday morning in Portland, where he expressed excitement about a unique challenge and appreciated the Celtics for giving him a heads-up that they’d trade him this offseason. Boston acquired Anfernee Simons in the deal, who’s yet to receive a uniform number or introduction himself from the Celtics.
“I was at home in California. I ended up getting a call from Brad, and he ended up telling me a little bit before,” Holiday said. “I was excited. I knew that obviously I got traded here before, so it was kind of full circle, talking to Chauncey (Billups) about it, talking to Joe (Cronin) about it and I really do appreciate what they did the first time around. “That really (did) mean a lot for me and my career. 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. So excited to be here.”
Brad Stevens also explained that he prepared Holiday, Kristaps Porziņģis and their agents for the possibility that they could depart Boston this offseason. They understood as veterans, he said, that the second apron put the Celtics in a difficult spot. Despite initial reports that Holiday didn’t like landing in Portland, Jake Fischer noted on The Garden Report that he received encouragement from Damian Lillard, who reached out and talked up the organization.
Only eight days later after Boston dealt Holiday, the Bucks released Lillard, who Holiday texted an emoji to. Holiday had long wanted to team up with Lillard, and while he’ll have to wait longer to play together due to Lillard’s achilles recovery, the surprise decision by Lillard to return to Portland invigorated Holiday’s interest in what the Blazers have planned ahead.
“Obviously, Dame loves Portland and he’s been here for years and I know his family is here,” Holiday said. “To be able to play with him on the same team is something I’ve wanted to do for a long time, even before I left New Orleans, that was something that I’ve always wanted to do. Being able to do it back here, especially with a team that Dame has really put on his back for a long time is really cool.”
The Blazers traded Lillard to Milwaukee in 2023 for Holiday and draft picks before Portland re-routed him to Boston for Robert Williams III, Malcolm Brogdon and additional draft selections. Cronin worked with Holiday on finding a preferable destination, and it resulted in Holiday winning his second NBA title immediately. In Milwaukee, Lillard lived in Holiday’s house while playing for the Bucks, and the pair Lillard revealed that one of their greetings before a Bucks-Celtics game involved him complaining to Holiday about the WiFi.
Lillard returning to the Blazers required desperation by the Bucks to maintain competitiveness as the clock ticks on Giannis Antetokounmpo’s time with the Bucks, along with an achilles tear that followed a blood clot that Lillard quickly recovered from before the playoffs. He’ll miss most if not all of the 2025-26 season before returning in full for his age-36 season. The Blazers are attempting to make the playoffs for the first time since 2020-21 after slowly rebuilding for four years under Chauncey Billups, who Holiday has admired. Portland won 26-of-44 from mid-January through April to finish three games back of the play-in. They’ve discussed offense, Holiday said, and praised the defense the Blazers played last season. He touted his position-less game and shooting as ways to fit in alongside Lillard and Scott Henderson.
“I think I’ve been in the game to know that it’s not always gonna be the brightest or the best or the easiest,” Holiday said. “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 play, because you feel like you’re part of something bigger than yourself.”
Otherwise the Blazers boast ascending young talent throughout their lineup, including Henderson, Deni Avdija, Donovan Clingan, who will take over for Deandre Ayton at center, along with Summer League sensation Yang Hansen, who impressed Holiday. Williams III, another former Celtic, hopes to recover from back-to-back-to-back injury-riddled seasons where he failed to reach 36 games.
Holiday didn’t address issues with his physical that reportedly led the Blazers to remove two second-rounders initially sent to Boston in the first reports about the trade. Portland ultimately felt comfortable to move forward with acquiring the 34-year-old, who has three-years, $104 million left on his contract. He dealt with knee, shoulder and groin issues last year before breaking his pinky finger before the playoffs and suffering a hamstring ailment that forced him to miss time in the first round. Holiday played 62 regular season games before appearing in 8-of-11 in the playoffs. This summer featured more rest after he played a significant role in the Olympics with Team USA last offseason.
“I can just be me,” Holiday said. “I don’t really know how to do anything else. Just come here and be the person that I’ve always been and try not to just help out as much as possible, but try to win. Obviously, with the organization and the coaching staff, they have a great coaching staff, Hall-of-Fame coach in Chauncey, but I think as a current player, who’s won, been through the struggle not too long ago to win a championship, I still have that feeling and that itch, so I’m closer to what that feeling is like and how hard it is to actually win.”
