With the Boston Celtics looking to slash their staggering payroll that would reach $500 million, including the luxury tax penalties, Bill Simmons of The Ringer proposed a wild trade that will break up their championship core.
Here is Simmons’ trade proposal:
Boston Celtics Receive: Fred VanVleet, Jabari Smith Jr., Tari Eason, 2025 No. 10 Pick
Houston Rockets Receive: Jaylen Brown, Jrue Holiday
Simmons, however, repeatedly noted that his trade proposal is just a “last resort” for the Celtics if they decide to part ways with Brown. Personally, he would not want for the Celtics to trade Brown.
The Celtics are potentially entering a gap year with Jayson Tatum expected to miss the most, if not the entire next season due to Achilles injury.
Simmons’ trade proposal will get rid of Brown’s $53.1 million salary and Holiday’s $34.8 million salary, giving them more financial flexibility to reset while awaiting for Tatum’s return.
On top of that, they get VanVleet, who can bridge their gap year or someone who can they flip for more assets. Smith and Eason are two young players with defensive upside who can play supporting roles to Tatum and Derrick White.
Jrue Holiday’s Uncertain Future

However, it is unlikely the Celtics will trade Brown. Holiday’s case though is a different story.
According to NBA insider Marc Stein, there are some degrees to the projected availability of their starters in the trade market this offseason, like they are more open to trading Jrue Holiday.
“The Celtics’ precise determination to keep their various veterans is difficult to calculate so soon after the defending champions’ Round 2 exit to the Knicks in six games and the devastating loss of Jayson Tatum to an Achilles rupture, but the early projections in circulation suggest Boston is more apt to make Jrue Holiday available via trade this offseason than Derrick White,” Stein wrote in his Substack newsletter, “The Stein Line.”
Amid the trade rumors, Holiday made it clear he wants to remain in Boston.
“I think we still have a really, really great opportunity and a great window to be successful and win a championship again,” Holiday told reporters after their second-round exit. “I think the talent that we have on this team, not only on the court, but the coaching staff, all the way up to Brad [Stevens], has been amazing. So, yeah, the opportunity to win is now, and I still want to be a part of that.”
Most Movable Celtics Player
Boston veteran center Kristaps Porzingis, who was a non-factor in the Celtics’ abruptly halted playoff run, is the most likely to get traded, according to Stein.
“Most rival teams continue to regard Kristaps Porziņģis as the most movable Boston vet thanks to the Latvian big man’s $30.7 million expiring contract,” Stein wrote.
The 7-foot-1 Latvian center played a pivotal role in his first season with the Celtics last year, which ended in Boston’s 18th championship. However, a mysterious respiratory illness rendered him ineffective in this dispirited Celtics playoff run, particularly in their second-round loss to the New York Knicks.
The 29-year-old center averaged just 4.2 points on 24% shooting across the six-game loss to the Knicks. He only played 15.5 minutes per game.