The Celtics will likely look different next season and big changes could be coming.
Aside from being without Jayson Tatum for a majority of the 2025-26 campaign — if not all of it — after undergoing successful surgery for a ruptured Achilles tendon, the Celtics will have decisions to make regarding their roster if they want to reduce their salary and luxury-tax penalties.
On a recent episode of “The Bill Simmons Podcast,” the longtime Boston sports fan floated a big blockbuster trade the Celtics could make that involves one of their biggest stars.
Simmons sends Jaylen Brown and Jrue Holiday to the Houston Rockets in exchange for Fred VanVleet, Jabari Smith Jr., Tari Eason and the No. 10 pick in the 2025 NBA Draft in his transaction.
Understandably, the hypothetical trade raised a lot of eyebrows on social media. So Simmons took to X to explain his reasoning behind the blockbuster.
“Repeatedly said I want them to keep Jaylen,” he posted on Monday night. “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."
Holiday’s name has been mentioned in trade speculation before the season even ended. NBA insider Marc Stein reported that the Celtics are “more apt to make Jrue Holiday available via trade this offseason than Derrick White.”
If the Celtics were indeed to move both Brown and Holiday’s contracts, they’d be under the second apron. But it’s unclear if Brad Stevens would think that return would justify trading away someone of Brown’s caliber — especially going into a season without Tatum.