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Celtics reunion could be key to Jaylen Brown-Trail Blazers blockbuster trade

Boston wants to reunite with this player. That could very well be part of the deal.
Oct 27, 2025; New Orleans, Louisiana, USA; Boston Celtics guard Jaylen Brown (7) reacts during the first half against the New Orleans Pelicans at Smoothie King Center. Mandatory Credit: Matthew Hinton-Imagn Images
Oct 27, 2025; New Orleans, Louisiana, USA; Boston Celtics guard Jaylen Brown (7) reacts during the first half against the New Orleans Pelicans at Smoothie King Center. Mandatory Credit: Matthew Hinton-Imagn Images | Matthew Hinton-Imagn Images

We are all eagerly anticipating how this Jaylen Brown situation will end. In a perfect world, the Boston Celtics would keep Brown, but the potential salary cap ramifications are simply too harsh for them to do that. That's why there's a market for him, and among the teams that make the most sense as a Brown destination are the Portland Trail Blazers.

The Trail Blazers have the draft assets and young players to get Boston's attention. One way they could work out a deal is by including Robert Williams III, as Marc Stein and Jake Fischer reported last night (and not the first time) that the Celtics want him back.

"It's believed that (Kevon) Looney is also on Boston's list of center targets, which is likewise known to feature former Celtics big man Robert Williams III," Fischer and Stein wrote.

Boston wants improvements around their frontcourt, and as a team that's firmly under the tax, they can also execute sign-and-trade. Since the Celtics alum is an unrestricted free agent, Boston use that to their advantage, especially if the Trail Blazers are serious about getting Brown.

Williams wouldn't (and shouldn't) be the main piece coming back, but he could be the key to orchestrating a deal, as it could prevent Portland from feeling like they're sending a few too many pieces to get Brown.

At this stage of his career, Timelord is more of a specialist

The Celtics' interest in Williams is pretty easy to comprehend. He has familiarity with the team and he has the talent to be a starter. The only reason why his market isn't stronger is because Williams is injury-prone.

Even though he is good enough to be a starting center (and has been one in the past), Timelord's inability to stay on the floor has been a running theme throughout his career. Up until this past season, it only got worse in Portland, as he appeared in only 26 games combined with the Trail Blazers in his first two seasons on the team.

That's why it may be a fool's errand to believe that Boston would bring him back to start, as it welcomes the risk of him getting hurt like it did back then. Portland figured this out by having him come off the bench in favor of Donovan Clingan.

The Celtics could absolutely do the same thing, but the point remains that if they want Timelord back, and there's good reason to, he would be a part of the return, but not THE return.

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