Jan 26, 2026; Boston, Massachusetts, USA; Boston Celtics guard Payton Pritchard (11) talks with Portland Trail Blazers guard Jrue Holiday (5) during the second half at TD Garden. Mandatory Credit: Bob DeChiara-Imagn Images
BOSTON — Monday night marked a unique, full-circle moment after a series of moves brought Jrue Holiday and Robert Williams III back to Boston for their first appearance on the TD Garden court since the Celtics traded both of them two years apart. They dealt Williams III as part of the package that brought Holiday to Boston from Milwaukee through Portland, and sent Holiday back to the Blazers this past summer for Anfernee Simons for salary, tax and apron relief.
“I think I already went through all that early in the season,” Holiday said, laughing after the Celtics defeated the Blazers. “It’s a part of the league, it’s a part of the life that I’m in, so it happens.”
When his post-game media session ended, Holiday took a moment to appreciate the madness that brought him back to the Blazers. He always appreciated the way they handled his surprise trade from Milwaukee, where he expected to retire, before they found a new home for him in Boston where he immediately helped deliver a championship. Now, Damian Lillard is his teammate, recovering from an Achilles injury that ended his Bucks tenure. Deni Avdija arrived in a trade with the Wizards that included Malcolm Brogdon and draft compensation — both arriving from the first Boston-Holiday trade.
Portland formed a new core from what they received in the Holiday and Lillard trades. And now Holiday and Lillard are back. The Blazers defeated the Celtics last month, while Holiday sat for one of the 27 games he missed with a hamstring injury. They lost, but won the final three quarters on Monday with a gritty defensive effort that they’re forming an identity around even with injuries plaguing their season alongside the loss of their head coach in October. Tiago Splitter assumed head coaching duties with federal officials arrested an indicted Chauncey Billups over alleged illegal gambling activity.
“I knew I was getting traded,” Holiday said. “Brad (Stevens) had told me it was a possibility, and then whenever it happened, he was up front and told me what happened. I felt like it was a great transition, me and my family are doing well in Portland, a lot of people that we actually know loved the organization from even before, when they actually traded me here, but to circle back and get me means a lot to me. So I’ve been doing well.”
It’s easy to imagine Portland emerging as a West playoff team next season when they return to full health. It’s unclear whether Williams III will return, now 28-years-old and trying to return to full health after surgeries derailed his first two Blazers seasons, where he combined to play in only 26 games. His health spiraled following a meniscus tear in 2022 when he anchored the Celtics’ top-ranked defense and finished seventh in Defensive Player of the Year voting. He underwent a follow-up procedure and missed the start of the 2022-23 season.
Upon arrival in Boston on Tuesday, Williams hadn’t faced his former team into his third season away. He still remembers the day the Celtics traded him, only days from training camp in 2023-24. Then, he watched long-time teammates win a championship without him, which sparked an admittedly conflicted feeling.
“I watched the whole Finals. I watched them win it,” Williams said on Monday. “Me and my girl, I went through a moment of saying I was happy for my dawgs, then I went through F-em, it was mixed emotions, but I’m glad they did it for sure.”
The reunions extended to Williams and Simons, the former Blazer who Williams spotted going through pre-game mobility tests near the Celtics’ tunnel as he made his way to pre-game chapel. They embraced before and after the game, while Holiday, who performed his own routine across the hall, ran into Neemias Queta, Xavier Tillman Sr. and Jordan Walsh, who quipped with Holiday about looking for gifted sneakers. Holiday shot back that Walsh wouldn’t fit in his shoes.
Former Celtics teammates and players swarmed Holiday after the game, renowned for his on and off-court impact during his two years in Boston. He even drew praise from Joe Mazzulla before the game, who typically avoids commenting on former players, even ones who starred in Boston. Williams’ own welcome back video on the Jumbotron amounted to an understated appearance alongside Brogdon during a timeout. For Holiday, a champion and transformative Celtic over a short span, he received a long tribute and ovation between the first and second quarters.
Brown recently praised Holiday’s contributions to their XChange business development program and emphasized that not many players make large contributions to a city they spend so little time in. In turn, Holiday shared little surprise that Brown led the Celtics to a successful first half of the season. Brown took doubts personally.
“I knew that they’d do well, knowing the type of determination that this coaching staff and organization has,” Holiday said. “Being with this team for a couple of years now and knowing the type of players that they are and how they prepare, I figured that they’d be good and obviously knowing Jaylen, I feel like he takes a lot of things personally, so he doesn’t accept a lot, especially when it comes to being bad.”
“That’s something I contemplate every day,” Tatum said. “More so about the team, if or when I do come back this season, they would’ve played 50 some-odd games without me. So they have an identity this year or things that they felt have clicked for them, and it’s been successful, right, third or second team in the East up to this point. So there is a thought in my head that’s like, how does that work or hows does that look with me integrating myself off an injury and 50-60 games into a season? There could obviously be some challenges and it is a thought, like damn? Do I come back or should I wait? It’s something that I honestly, recently in the last two weeks or so, just kind of contemplate every single day.”
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