Windhorst Says Jaylen Brown, Jayson Tatum's Future Must Be Evaluated by Celtics amid Trade Rumors

ESPN's Brian Windhorst believes the Boston Celtics "have to evaluate their roster" and decide if having Jaylen Brown and Jayson Tatum's contracts together on the team is the right move in today's NBA under the new collective bargaining agreement, which features stricter penalties for teams who go above the salary cap.

"I think the Celtics are at an interesting point," Windhorst said. "They have to evaluate their roster and decide is Jaylen Brown and Jayson Tatum together earning $600 million on their contracts the way to go forward in the league, in the apron era to have everything tied up in two players that are so similar.

"Not because one guy wants his own team, not because one guy wants out of there, not because one guy wants extra accolades and extra shots. From a basketball team-building strategic standpoint in the 2026 NBA, does that make sense? This is what the Celtics have to analyze."

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

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 those players were dealt last offseason, and Boston's prospects looked a bit bleak for 2025-26, especially with Tatum having suffered a torn Achilles in the playoffs against the New York Knicks last May.

However, Brown had a breakout year, and the Celtics impressed en route to a 56-26 season that landed the squad second in the Eastern Conference. Tatum even returned before the end of the season and played 16 games.

The Celtics' postseason ended quickly, however, as the seventh-seeded Philadelphia 76ers upset Boston in seven games in the first round.

Obviously, a healthy Tatum and Brown brings optimism for the 2026-27 season. However, there has been some trade speculation regarding Brown, which seems like a near-annual exercise at this point.

League insider Chris Mannix revealed on NBA on NBC earlier this month that the Atlanta Hawks reportedly had "a brief conversation" about Brown last offseason and added that they could still get "interested in" him.

And both Windhorst and NBA insider Jake Fischer spoke about the hypothetical possibility of a trade involving Giannis Antetokounmpo heading to the C's (h/t B/R's Doric Sam).

Via Windhorst: "This is extraordinarily simple. Of course Milwaukee would see some of the stuff that Jaylen Brown is saying and they would get ready to go and call Boston," Windhorst said. "From a Boston standpoint, this is very simple. In July, Jaylen Brown has the opportunity to sign a contract extension with the Celtics. If he's happy with the Celtics, it's a huge one. It could be $70 million per year. He's just coming off his best season, you're going to offer it. If he's happy with the Celtics, sign. See you in September. If he's not happy with the Celtics and he's like, 'I'm not sure I want to be here,' trade [him]."

From Fischer: "If — and I want to stress that this is a hypothetical — any Brown-for-Antetokounmpo conversation actually does materialize in the future, multiple rival team strategists this week suggested that the likely appeal for Milwaukee, in addition to draft capital from the Celtics, would be to move Brown on or expand such a deal into a multi-team transaction."

Needless to say, there's been some chatter. As of now, the Tatum-Brown combo still leads the Celtics and gives the team a chance for the championship ever year.