The Boston Celtics are supposed to be contenders. Not just contenders. Dynasties. That was the plan when they locked up Jayson Tatum and Jaylen Brown to supermax contracts that will pay them a combined $120 million per season. Two wings. Two stars. Two cornerstones.
But then the 76ers happened. A 3-1 lead evaporated. A first-round exit that nobody saw coming. And now, for the first time in the Tatum-Brown era, the Celtics are at a real crossroads.
Not a fake crossroads. Not a “we need to tweak the bench” crossroads. A real one.
Jaylen Brown, Celtics
Bill Simmons and Zach Lowe of The Ringer spent part of their Sunday podcast dancing around the question that every Celtics fan is afraid to ask: should Boston trade Jaylen Brown?
Simmons was blunt.
That’s not a basketball question. That’s an accounting question. And in the modern NBA, accounting questions become basketball questions very quickly.
The math is staggering. Over the next three seasons, Brown and Tatum will collectively earn more than $350 million. That’s not a typo. Three hundred fifty million dollars. For two players. In a league with a salary cap that restricts how much teams can spend.
The Celtics can afford it. They have rich owners. They have a big market. They have lucrative television deals. But “can afford” is not the same as “should afford.” At some point, the cost of keeping both stars becomes an obstacle to building a team around them.
Simmons and Lowe talked about potential trade scenarios. The headliner, of course, was Giannis Antetokounmpo. If the Bucks ever decide to move on from their two-time MVP, the Celtics would be right in the mix. And Brown would almost certainly be the centerpiece of any package going back to Milwaukee.
“I think [the Celtics] would be one of the contenders for Giannis, and I think Jaylen as an asset that either goes back to Milwaukee or goes to a third team, and then that team gives their stuff to Milwaukee would be how that trade goes,” Simmons said.
That’s the nightmare scenario for Celtics fans who grew up watching Brown develop from a raw rookie into an All-NBA superstar. Trading him would feel like a betrayal. It would feel like giving up on the core that finally won a championship in 2024.
But Simmons raised another possibility. One that has nothing to do with the Celtics wanting to move Brown. One that has everything to do with Brown wanting to move himself.
“What if Jaylen Brown goes to the team and says, ‘It’s time, I want my own team,'” Simmons asked Lowe. “We’ve seen weirder things in the NBA than Jaylen Brown deciding, ‘I’d like my own team now.'”
Think about that. Brown is 29 years old. He just finished the best season of his career. With Tatum sidelined for much of the year, Brown averaged career highs in points (28.7), rebounds (6.9), and assists (5.1). He was the man. He carried the Celtics to the second seed in the Eastern Conference.
And then the playoffs happened. Tatum was still hurt. Brown carried the load. But it wasn’t enough. The Celtics lost to a 76ers team they should have beaten. And Brown, for all his brilliance, couldn’t will his team past the finish line.
That’s not a criticism. That’s context. Brown is a superstar. But he’s not a top-five player. He’s not Giannis. He’s not Luka. He’s not the kind of player who can single-handedly drag a team to a championship.
And maybe, after 10 years of playing second fiddle to Tatum, Brown is ready to find out if he can be that guy somewhere else.
The irony is that Brown just called this past season his favorite year in the NBA. Less than two years removed from winning a championship and earning Finals MVP honors, Brown said on his post-elimination livestream that the 2025-26 campaign meant more to him than any other.
“I wish we trusted that style of play a little bit more, but I know the playoffs kind of shifted our rotations and what we wanted to do,” Brown said. “But I am so proud, and it was my favorite year of my basketball career.”
That’s not the comment of a player who is miserable. That’s not a trade demand wrapped in polite language. That’s a player who found joy in carrying a team, even if that team ultimately fell short.
But joy and ambition are different things. Brown can be happy with his season and still want more. He can be proud of what he accomplished and still wonder what it would be like to be the unquestioned leader of his own franchise.
Simmons said he hopes Brown and Tatum play their entire careers together in Boston. That’s the romantic version. Two homegrown stars, two friends, two champions, growing old in the same uniform.
But the NBA is not a romantic league. It’s a business. And businesses make hard decisions.
The Celtics have to decide if paying two players $120 million a year is sustainable. They have to decide if the Tatum-Brown partnership has run its course. And they have to decide if the package they could get for Brown – whether it’s Giannis or a haul of draft picks and young players – would put them in a better position to win.
Here’s the bottom line: Jaylen Brown just had the best season of his career. He proved he can be the man. He proved he can carry a team. And now, at 29, he might finally be ready to do it somewhere else.
The Celtics are at a crossroads. So is Brown.
We’ll find out this summer which direction they both choose.