The Boston Celtics’ 119-81 blowout loss to the New York Knicks in Game 6 not only ended their hopes of a second consecutive NBA title, but it may also signal the end of an era for the current core of Jrue Holiday, Derrick White, Jaylen Brown, Jayson Tatum, and Kristaps Porziņģis.
According to ESPN’s Bobby Marks, Boston is projected to have $464 million tied up in salary and repeat luxury tax penalties next season. If the Celtics keep their draft picks, avoid trades, and round out the roster with minimum contracts, that figure could exceed $500 million. It’s unlikely that new team owner Bill Chisholm will want to invest that much into a group that fell short of even reaching the Eastern Conference Finals.
To make matters worse, the Celtics lost Jayson Tatum for the foreseeable future after he suffered a ruptured Achilles tendon in Game 4. Without their star, Boston is no longer a serious title contender next season. Given the circumstances, the front office may have to consider retooling—moving some of the high-priced veterans in exchange for younger talent and future assets.
Bill Simmons’ Proposed Celtics Trade Is a Good Idea
On his popular podcast, Bill Simmons floated a blockbuster trade idea involving the Houston Rockets, who were recently ousted by the Golden State Warriors in the first round of the playoffs. The proposed deal would send Jaylen Brown and Jrue Holiday to Houston in exchange for Fred VanVleet, Jabari Smith Jr., Tari Eason, and the No. 10 overall pick in the upcoming NBA Draft.
This potential trade could benefit both sides. Houston would land Holiday, a battle-tested, two-time NBA champion and elite defender, along with Brown, one of the league’s premier two-way wings and a reliable closer. Boston, meanwhile, would receive a strong return: VanVleet, a championship-winning point guard (14.1 PPG, 3.7 RPG, 5.6 APG), Eason, a 24-year-old wing who averaged 12 points and 6.4 rebounds, and Smith Jr., a versatile 22-year-old big man who put up 12.2 points and 7 boards per game.
The real bonus for the Celtics is the 10th overall pick, which could be used to draft a potential cornerstone like Maryland center Derik Queen, or as trade bait along with the 28th pick to acquire additional assets.
While Boston would be parting with the best player in the deal and dismantling one of the NBA’s top wing duos, the move could be a necessary financial reset. Offloading Brown and Holiday would help them escape the punitive second apron of the luxury tax and provide a path toward long-term sustainability—without a full-scale rebuild.
Faced with injuries, sky-high payroll, and rising pressure, this deal could give the Celtics the flexibility and future upside they need, even if it’s not the route fans envisioned.