Bill Simmons Fuels Jaylen Brown Trade Speculation: Are the Celtics Considering a Core Shake-Up?
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The Boston Celtics just hoisted Banner 18, their long-awaited return to the top of the NBA mountain. But even in the aftermath of a title, the talk hasn’t slowed down. If anything, it’s accelerated—and this time, the conversation isn’t about celebration. It’s about the future.
And once again, The Ringer’s Bill Simmons is at the center of the storm.
In a recent episode of The Bill Simmons Podcast, the Celtics superfan and media mogul stirred the pot, suggesting that Jaylen Brown—fresh off winning Finals MVP—might not be as untouchable as Celtics fans would like to believe.
“There’s a world where Boston has to look at the books and say, ‘Can we really carry two $300 million guys?’” Simmons said, referencing the supermax contracts of Jayson Tatum and Jaylen Brown. “I love Jaylen. I’ve always been Team Jaylen. But it wouldn’t totally shock me if the front office explored some things. Especially if the right player becomes available.”
That’s all it took. Celtics Twitter? Exploded. Reddit? On fire. Trade machine enthusiasts? Working overtime.
But beneath the noise, there’s a real question hiding in plain sight: Could the Celtics really trade Jaylen Brown?
The Numbers Game
Jaylen Brown signed a five-year, $304 million supermax extension in July 2023, the richest contract in NBA history at the time. Jayson Tatum is expected to ink a similar deal this offseason, likely pushing Boston’s payroll into the stratosphere under the NBA’s new collective bargaining agreement.
With the second apron looming—a hard cap threshold that restricts roster flexibility, punishes spending, and limits trades—teams have to be brutally honest about their finances. Depth becomes harder to maintain. The ability to absorb contracts or sign mid-level free agents disappears.
Brad Stevens has done a masterful job constructing a contender, flipping Marcus Smart, Robert Williams, and Malcolm Brogdon into Kristaps Porziņģis and Jrue Holiday. But that kind of creativity gets harder under the new CBA.
And that’s where Simmons’ speculation finds its footing. The Celtics might want to keep Brown and Tatum together forever. But the new CBA might force them to choose.
Why Brown Might Be on the Block
Brown’s trade value has never been higher. He just led Boston to a championship, played elite defense throughout the playoffs, and silenced doubters who questioned whether he could be a No. 1 option in high-pressure moments.
If Boston were ever going to sell high, this would be the moment.
You could argue that Brown’s skill set—athleticism, elite perimeter defense, slashing—could be replicated more cheaply, allowing Boston to bring in a more cost-effective scorer or bolster their bench.
Alternatively, Brown could headline a package for a younger star on a cheaper deal, or be used to pivot toward a more traditional playmaker to diversify Boston’s offense.
Imagine a scenario where the Celtics trade Brown for someone like Donovan Mitchell (if Cleveland implodes), or even a bold swing for Luka Dončić or Shai Gilgeous-Alexander if one of those stars ever becomes disillusioned. Far-fetched? Maybe. But that’s the kind of thinking that could justify breaking up a title-winning duo.
Why It Would Be a Mistake
Let’s be clear: the Celtics should not trade Jaylen Brown.
He just delivered a championship. He’s the heart and soul of Boston’s defense. He’s improved every year. His relationship with Tatum is strong, and they’ve grown together since they were teenagers.
Financial pressure is real—but so is chemistry. So is trust. So is culture.
The idea of trading Brown to duck the second apron feels more like a panic move than a calculated one. There’s no guarantee a trade would make the team better, and disrupting a championship formula is a massive risk.
If the goal is to win multiple titles, you don’t mess with what works.
What Simmons Really Meant
It’s worth noting: Bill Simmons wasn’t calling for a trade. He was speculating. But his speculation carries weight. He’s deeply connected to the Celtics and often reflects whispers he’s hearing behind the scenes.
So, is this smoke? Or fire?
It’s probably somewhere in between. Simmons likely knows Boston’s front office is feeling the pressure. They’re staring down the most expensive roster in NBA history. They’re watching the league tighten the financial screws.
And they’re aware that, in this new NBA economy, hard decisions are coming—maybe not today, maybe not this season, but soon.
The Verdict
Right now, there’s no concrete indication that Boston is shopping Jaylen Brown. This feels more like offseason talk than real trade momentum.
But Simmons’ comments highlight a growing reality in the league: superteams are getting more expensive, and even the best franchises are going to be tested by the CBA’s punitive rules.
Could Boston explore their options? Sure. But they’d be foolish to break up a championship core unless the return is unquestionably better.
And let’s be honest—how many players are better than Jaylen Brown and actually available?
For now, Celtics fans can breathe easy. Brown and Tatum are on top of the basketball world. But Simmons’ words are a warning: the price of success has never been higher.
And eventually, someone in Boston’s front office might have to ask the hardest question in sports: Can we afford to stay this good for this long?
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