Bill Simmons proposes wild Celtics-Rockets trade centered on Jaylen Brown
Simmons' proposed trade would send by Jaylen Brown and Jrue Holiday to the Houston Rockets.
Changes will be coming for the Boston Celtics this offseason.
Not only will Boston have to grapple with the real possibility that Jayson Tatum could miss most of — if not the entire — 2025-26 season while recovering from a ruptured Achilles’ tendon, but Boston also needs to shed significant salary this summer in order to alleviate the team’s incoming luxury-tax penalties.
And while most trade scenarios centered around the Celtics this summer have revolved around high-priced supporting players like Jrue Holiday and Kristaps Porzingis, longtime basketball writer Bill Simmons tossed out a radical, blockbuster deal on Sunday night that would send Celtics star Jaylen Brown to the Houston Rockets.
Speaking to Ryen Russillo on Sunday, Simmons tossed out a potential trade involving several moving pieces between the Celtics and Rockets:
Boston Celtics Receive: Fred VanVleet, Jabari Smith Jr., Tari Eason, 2025 No. 10 Pick
Houston Rockets Receive: Jaylen Brown, Jrue Holiday
Simmons took to X on Monday to further expand on the rationale behind his trade proposal:
“Repeatedly said I want them to keep Jaylen,” Simmons posted. “Was only saying if they decided as a last resort they had to deal him cuz of the 2nd apron — it would have to be a deal that looked something like this, where they shed $20+ million in trade and get a few assets back.”
Moving both Brown ($53.1 million salary in 2025-26) and Holiday ($32.4 million salary) off of Boston’s books would help Boston get under the second apron — lessening those luxury-tax penalties and giving Brad Stevens more freedom to augment the roster in the years ahead.
Still, it remains to be seen if the return from Houston would be worth giving up a star in his prime like Brown.
Jabari Smith, 22, would be a solid piece for a revamped Celtics core moving forward — with the former Auburn standout averaging 12.2 points and 7.0 rebounds over 57 games last season.
Eason, 24, also would be a young asset with solid numbers (12.0 points, 6.4 rebounds per game) with room to grow — while VanVleet is a veteran guard who could still put up points on a reworked Celtics roster.
But one would assume that the Celtics would ideally target Houston’s top young asset like Amen Thompson in any potential blockbuster involving Brown — while Houston is already projected to be over the salary cap in 2025-26.
If the Celtics do entertain a scenario where they trade Brown to help get under the salary cap (and retool around Tatum in the coming years), could Boston potentially try to pry the No. 1 pick in the 2025 NBA Draft (Maine native Cooper Flagg, in all likelihood) away from the Dallas Mavericks?
It’s unclear if the Celtics could successfully entice Nico Harrison and a win-now Mavericks roster to bite on such a deal, but former NBA executive and current columnist for The Athletic John Hollinger said that Boston could make a compelling pitch.
“The other avenue, we must whisper, is asking Boston about Jaylen Brown,” Hollinger wrote last week. “Brown is a much easier positional fit next to [Anthony] Davis and [Dereck] Lively, but he’s owed $236 million over the next four seasons, and the Celtics’ roster gets frighteningly expensive next season.
“Would Boston mind resetting around a New England native [in Flagg] and waiting out a gap year if Tatum needs it to recover? For that matter, would Dallas do this unless it also had considerable capital coming back in addition to Brown?”
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