In a recent episode of his podcast, Bill Simmons said he believes the biggest reason the Boston Celtics traded Jaylen Brown this offseason was that he and Jayson Tatum had reached their peak as a duo, and that their success "wasn't sustainable."
"They thought they ran their course with [Jaylen Brown and Jayson Tatum], and that was that. They hit the wall, and they wanted to do this now instead of a year from now. And that it wasn't sustainable," Simmons said about the Jaylen Brown trade.
And to be honest, I think I agree.
The Jays wouldn't have won another championship together in Boston
Tatum and Brown definitely had a lot more left in the tank as a duo. They are 28 and 29 years old, respectively, and they had already accumulated so much success together (one NBA championship, two Finals appearances, and five conference finals appearances -- they also never missed the playoffs as teammates).
But at the same time, the ratio of heartbreaking finishes (losing to the Miami Heat in the 2020 conference finals, losing in the 2022 NBA Finals to the Golden State Warriors, losing to the No. 8 seed Heat in 2023, losing to the New York Knicks in the second round in 2025, and the 3-1 first-round collapse against the Philadelphia 76ers earlier this year) to championships was way too high.
And it took a basically perfect situation for them to win it all in 2024, namely the Kristaps Porzingis and Jrue Holiday additions just as the new CBA kicked in, and players like Donovan Mitchell and Tyrese Haliburton missing games against them in the playoffs.
The truth is that the Jays were an incredible duo that made an impact in Boston, but the stars were never going to align the way they did in 2024. And on top of that, there were serious concerns about their long-term fit going forward. They never truly complemented each other on the court, and the whole 1A-1B dynamic was only going to get worse for Brown and Tatum as they inched closer to the end of their peaks.
Pair that with the rest of the Eastern Conference climbing up the ladder, and it would have been incredibly difficult for the Celtics to establish themselves as legitimate powerhouses again if they signed Brown to a new deal.
Not extending Jaylen Brown was the right call for the Celtics
This almost pains me to even write this. I've been a huge Brown supporter even before Boston drafted him third overall in 2016, and I don't necessarily expect that to change now that he is in Philadelphia. But I think the Celtics made the right decision not signing him to a contract extension this offseason.
The Georgia native was eligible for a two-year, $142 million contract extension this offseason. If the Celtics had signed him to that deal to pair alongside Tatum's five-year, $313.9 million contract (which runs through the 2029-30 season), then the two of them would have made up for way too much of the team's cap. It would have been impossible for them to bolster the rest of the roster and either extend players already on the team or bring in outside reinforcements.
It became a huge meme in the Celtics community in the summer, but Brad Stevens was right: this trade gives them the flexibility and "optionality" they need to compete in the long run.
Brown is a great player, and he was a great Celtic. His number should absolutely be hanging in TD Garden one day, and nobody can ever ignore his legacy in Boston. But the Celtics were also right to trade him, and they were never going to accomplish their ultimate goal of winning Banner 19 had they kept him around for the long haul.
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