With a take this inflammatory, we must all operate with the same basic assumptions. Here are mine: The Boston Celtics probably do not want to trade Jaylen Brown. He is eligible for a two-year, $141.9 million extension in July, and I expect they will offer it to him. I have no idea if Brown wants to sign said extension, and if he doesn’t, they will trade him. That is, as we say in the biz, that.
Because of the contract situation, we really don’t have to speculate much on if he will be traded or not; the fountain pen and the expensive piece of paper will do the talking. But we can certainly wonder if Boston should proactively move past the Jaylen Brown era (short answer: no) or if Brown himself is starting to think past his time as a Celtic (short answer: probably, but everyone thinks about their future).
But then there’s the keystone question, one that is the genesis of this whole discussion and the reason I’m writing this at all: should Jaylen Brown want a trade now, and could that ultimately be good for Boston? (short answer: I think so)
Should the Celtics want to trade Jaylen?
If I’m Brad Stevens and Boston’s front office, I’m not getting in the habit of proactively trading All-NBA players who won a championship and Finals MVP for your franchise. The Celtics are no longer in dire financial straits, and it would be pretty cold to say “thanks for your service Jaylen, peace out!” without having your hand forced. Jaylen isn’t even 30 yet, just had the best season of his career and has the two best abilities a superstar can have: durability and availability. Boston would be stupid to throw that away.
But Brown is not just a contract or a stat sheet; he’s a guy with personal and professional priorities. I don’t know if those are still best served in Boston, and Brown and I might be on the same page.
Brown’s reaction to their recent first-round series loss to the Philadelphia 76ers hasn’t exactly been gracious, and he even said that this season was his “favorite year” of his career. Not crazy because it was easily Brown’s best statistical season, but also not really a team-first view either, given that they won the NBA Finals in 2024, this was the first time the Celtics had missed the second round of the playoffs since 2021 and this was Brown’s first major stretch of his career without Jayson Tatum since he was a rookie.
“Where there’s smoke, there’s fire” is not true whatsoever (ever heard of a smoke machine?) but I don’t think Jaylen is saying this stuff just… cuz. It feels like a soft launch of a trade request, or at the very least, a cup of coffee with one. And I wouldn’t blame him, given we all just saw the best Jaylen Brown ever is one without Jayson Tatum on the floor. If you were Jaylen, you’d at least be wondering what life would be like if that were all the time, right?
Brown is not going to find that arrangement in Boston. Put simply, Tatum is a significantly better player than Brown and one the Celtics are more financially tied to. He will be healthy next season and regain his status as the primary creator and ball handler. Does Brown actually want to return to his old role?
How Jayson and Jaylen work in 2026 and beyond
The “Can Tatum and Brown win together?” debate… thing that dominated Celtics circles for over half a decade was finally put to rest when they, ya know, did. But personally, I always found both sides of the argument profoundly stupid. For one, it implied that this was an equal partnership, which it basically never was; Tatum’s dribble advantage always ensured he would dominate the ball. For another, it had this weird, New England Puritanical determinism bent to it; it was like you had to decide if you were committing your whole heart and soul to this core or if you were 100 percent out. God had already decided whether this was the right path, so you were either on the bus to salvation or nowhere near it.
I, conversely, always felt that trading Brown would make sense if I could be sure the Celtics would get better. Some Kevin Durant smoke back in 2021 piqued my interest, as did some 2019 Anthony Davis packages. For who those guys were at the time, Jaylen included, we were just talking about a categorical upgrade for Boston. It was always a question of how valuable Brown was to Boston versus how valuable he was to other teams.
And it’s the same deal now. Before the Celtics won it all in 2024, Brown’s value as an asset never exceeded his impact as a player. But it’s a brave new world in Boston, and Jaylen’s ability to be an elite first option may entice some interested teams to part with some serious beans to give Brown what he will never have on the Celtics: his own show, with all the trappings of superstardom and franchise control. How could he possibly avoid thinking about this?
Brown and Tatum have been extremely productive colleagues, but any suggestion from the Tatum-Brown Eternal Cult that they are blood brothers who never want to be separated ignores plenty of counter evidence. Logan Murdock’s excellent profile of Brown for The Ringer in 2023 explored the two’s relationship at length, and while the crux was basically “there has never been any conflict between them and that they’re good friends,” it also wasn’t “this guy is my ride or die forever, and I couldn’t imagine playing basketball without him.” Nor did Brown say much this year about how much he missed the then-injured Tatum on the court and how excited they all were to have him back. Calling this his “favorite year” isn’t super endearing either.
It was never a personal conflict, and I will resist to no end any notion that it was, but there has been obvious basketball friction between the two; they never ran much of a two-man game like some sort of Nikola Jokic/Jamal Murray duo, and both are most comfortable with the ball in their hands. Then again, find me a pair of superstars in NBA history that have been completely, 100 percent without a basketball conflict. Michael Jordan and Scottie Pippen? Absolutely not. Kevin Durant and Russell Westbrook? Nope. Shaquille O’Neal and Kobe Bryant? Are you kidding me?
I think Pippen/Jordan is very instructive, as while Pippen was better than Brown is now, and Jordan was uh, better than Tatum, you have to wonder if Jaylen knows the first word everyone thinks of when they think Scottie Pippen: sidekick. It wasn’t until Jordan retired that Pippen left the Chicago Bulls, and, already past his prime, his production plummeted. Does Brown really want to be remembered as a sidekick? Or does he want a fabulous second act to his career? Personally, I would want the second act.
What does Jaylen Brown want?
As I said before, Brown can force Boston’s hand by refusing to sign the extension they will offer him. That will speed things along, and then Boston will try to get the best deal they can; you’ll notice I avoided speculating about Giannis Antetokounmpo or any of the other packages thrown out on social media because they would have distracted from the crux of the issue: should Jaylen Brown actually want this, but an Antetokounmpo swap with Boston attaching a pick or two would probably be good for both parties. I wonder if Milwaukee would actually trade Giannis to Boston of all places — that would be a Category 5 betrayal of their fans — but Brown is probably by far the best player they could get back. Meanwhile, Tatum-Giannis-Derrick White is another category upgrade. His media circus and durability would make me nervous as a Celtics fan, but this is Giannis Antetokounmpo we’re talking about — still a business you want to be in.
But again, this really will be Brown’s decision, and I am essentially at peace with the fact that the right one for him might be to take his talents someplace else. He spent nine years in Boston blowing through every expectation and ceiling ever put on him, by me and many others, and I would be happy for him to be here another nine as a Celtic. But I also want him to be happy as Jaylen Brown; if it is no longer in Boston, that is, as we have said, that.
