Are the Boston Celtics on the verge of a complete rebuild?
With Jayson Tatum set to miss the entire 2025-26 season while recovering from an Achilles rupture, rumors are swirling around Boston.
World-class executive Brad Stevens is expected to make significant roster adjustments this summer to improve his club's financial outlook, and according to some, Jaylen Brown is not untouchable.
On Sunday, The Ringer's Bill Simmons wondered aloud about a trade idea involving Brown and another Celtics NBA champion that would send Boston fans into violent revolt if it came to fruition.
Simmons, on a new episode of The Bill Simmons Podcast, set the stage for the eye-opening trade idea by first lamenting the state of the NBA's collective bargaining agreement and salary constraints, which he feels are eroding the beauty of long-term team-building.
Follow The Sporting News on WhatsApp
“What they’ve created is a league where you can’t keep Tatum and Brown together, and you can’t keep core people together because you can’t afford to do it," Simmons said.
"And if you try to keep the two together, you can’t put anyone else around them.”
“This is just the way it is. You’re gonna have these three, four-year windows, and then you’re gonna have to blow it up.”
“When I think of (a Jaylen) Brown trade … it probably is the one that makes the most sense on paper, but that means we’re splitting up Tatum and Brown, which is something I never wanted them to do, and it might be the only move.”
“If Houston was gonna say, ‘We’ll take Jaylen and Jrue (Holiday), and we’ll give you (Fred) VanVleet back, and Jabari (Smith Jr.) and (Tari) Eason, and we'll give you the (No. 10) pick, you’ll save $20 million. We can make it work with our cap' ... that gets (the Celtics) under the second apron and into a rebuild. I think they would have to think about deals like that.”
“Then if you’re Houston, and you can get Jaylen and Jrue in the same trade and give up assets but not trade (Amen) Thompson and not touch (Alperen) Şengün … that’s (good for them).”
“But for me, trading Jaylen is an all-time last resort. There has to be a better option.”
Simmons deserves some grace here, as he might still be reeling from the Tatum injury and Boston's depressing exit from the playoffs. But on the whole, this would be a horrid deal for the Celtics.
Trading Brown is one thing (and a controversial thing at that), but losing both Brown and Holiday in a deal where Houston holds onto all of its best players would be a fleecing of historic proportions, even for a trade designed mostly to dump salary.
If Houston was willing to send over either Şengün or Thompson in the exchange, then a conversation could be had.
More NBA: Celtics turn heads with surprising Cooper Flagg decision; Trade coming?