Windhorst: Celtics Must Reassess Brown, Tatum Together

Celtics must – Brian Windhorst argues Boston must evaluate whether keeping Jaylen Brown and Jayson Tatum together—both earning huge figures under the NBA’s new collective bargaining rules—makes sense in the league’s apron era. The debate sits against an offseason shaped by a

For Boston, it isn’t just about talent. It’s about math, timing, and risk—especially now that the salary-cap landscape has tightened.

Brian Windhorst framed the decision in plain terms: the Celtics “have to evaluate their roster” and decide if having Jaylen Brown and Jayson Tatum on the team. with their contracts together totaling $600 million. is the right direction “in the apron era. ” when the new collective bargaining agreement brings “stricter penalties for teams who go above the salary cap.”.

Windhorst’s point wasn’t driven by trade rumors alone. “From a basketball team-building strategic standpoint in the 2026 NBA. ” he said. Boston has to analyze what it means to keep everything tied up in “two players that are so similar.” He also ruled out the usual narratives—wanting a trade. seeking personal accolades. or demanding extra shots—saying the evaluation comes down to roster construction and what makes sense as the league rules evolve.

That question hits the Celtics at a moment when their recent moves were shaped by the same problem Windhorst is pointing to: the cost of getting trapped near the league’s financial thresholds. Boston president of basketball operations Brad Stevens previously told reporters the team traded both Kristaps Porziņģis and Jrue Holiday. who were key members of the 2023-24 championship team. to avoid the dreaded second apron. Both players were dealt last offseason. and Boston’s prospects looked bleak for 2025-26—particularly after Tatum suffered a torn Achilles in the playoffs against the New York Knicks last May.

What changed is that the Celtics didn’t collapse. Brown had a breakout year, and Boston rolled to a 56-26 season that landed the team second in the Eastern Conference. Tatum even returned before the end of the season and played 16 games.

But the playoffs delivered another kind of jolt. Boston’s postseason ended quickly as the seventh-seeded Philadelphia 76ers upset the Celtics in seven games in the first round.

A healthy version of Tatum and Brown still carries real promise for 2026-27. Yet the offseason conversation hasn’t gone quiet, because the team’s on-paper stability is also tied to extremely expensive, long-term deals that stretch across multiple seasons.

Brown is under contract through the 2028-29 season on a five-year, $303.7 million supermax extension. Tatum’s deal runs for five years and $314 million through the 2028-29 campaign as well.

Trade speculation has swirled around Brown even as the Celtics keep proving they can contend. The chatter has followed a familiar rhythm—“a near-annual exercise,” as the coverage puts it—despite Brown’s rise and the Celtics’ overall success.

League insider Chris Mannix, speaking on NBA on NBC earlier this month, said the Atlanta Hawks reportedly had “a brief conversation” about Brown last offseason. Mannix also added that they could still get “interested in” him.

Windhorst then laid out how the situation could look from another angle. describing a straightforward path based on free-agency timing and leverage. “This is extraordinarily simple,” he said. “Of course Milwaukee would see some of the stuff that Jaylen Brown is saying and they would get ready to go and call Boston.”.

From a Boston standpoint, Windhorst said, the logic is also direct. In July, he explained, Brown has the opportunity to sign a contract extension with the Celtics. If Brown is happy. Boston would offer a huge deal—Windhorst suggested it “could be $70 million per year”—and then Brown would sign. “See you in September.” If Brown isn’t happy and says “I’m not sure I want to be here. ” Windhorst said. Boston would trade him.

Jake Fischer echoed a similar hypothetical. “If — and I want to stress that this is a hypothetical — any Brown-for-Antetokounmpo conversation actually does materialize in the future. ” Fischer said. multiple rival team strategists suggested the likely appeal for Milwaukee would be to move Brown on or expand such a deal into a multi-team transaction. Fischer also said Milwaukee would likely seek draft capital from the Celtics.

All of it adds up to the same pressure point Windhorst described at the start: the Celtics can’t treat their core as untouchable just because it works on the court. They have to decide whether those contracts together—and their financial consequences under the new rules—fit the way Boston wants to build and compete.

As of now. the Celtics’ championship case still rests on the Tatum-Brown combo. and it remains the team’s best bet to have a shot “ever year.” But in the apron era. even the most proven pairing comes with a new question: not whether Brown and Tatum can carry a team—whether Boston can afford to carry them. and still move the roster when the league demands flexibility.

Boston Celtics Jaylen Brown Jayson Tatum Brian Windhorst Brad Stevens apron era collective bargaining agreement salary cap trade rumors Philadelphia 76ers Atlanta Hawks Giannis Antetokounmpo Kristaps Porziņģis Jrue Holiday