Brad Stevens, Boston Celtics
Photo by Brian Fluharty/Getty Images
Brad Stevens, Boston Celtics
The Boston Celtics have never been shy about reshaping their roster. This summer has already been one of their most turbulent in recent memory, with Jayson Tatum rehabbing an Achilles injury and the front office balancing luxury tax constraints against the need to remain competitive.
One name now at the center of trade chatter? Anfernee Simons. His scoring talent is undeniable, but so is the $25 million annual salary attached to his deal. For a team roughly $12 million away from clearing the luxury tax, moving Simons might be more about flexibility than fit.
That’s where a proposal from NBC Sports Boston’s Chris Forsberg comes in — sending Simons to the Chicago Bulls in exchange for three younger, cost-controlled players.
The Framework
Boston Celtics receive: Ayo Dosunmu, Jalen Smith, Dalen Terry
Chicago Bulls receive: Anfernee Simons
Simons Out, Dosunmu In
Simons is a proven scorer, but with Jaylen Brown, Derrick White, and Payton Pritchard all poised for significant roles, his value in Boston looks redundant. His contract also makes him harder to justify on a tax-heavy roster.
Enter Ayo Dosunmu. At just 25, Dosunmu has grown into one of Chicago’s most dependable young guards. He defends multiple positions, makes smart decisions, and provides steady playmaking — a perfect glue guy for a Celtics team that will need stability while Tatum recovers.
As Forsberg explained: “Dosunmu better fits the mold of a long-term piece” in Boston’s system.
The Boston Celtics are expected to start Payton Pritchard and have Anfernee Simons come off the bench, per @GrantAfseth
“The Boston Celtics appear poised to elevate Payton Pritchard into the starting lineup while using Anfernee Simons as a high-scoring option off the bench for… pic.twitter.com/M6FuG6MELu
— NBACentral (@TheDunkCentral) August 14, 2025
Smith and Terry: Depth for the Celtics
The second piece of this deal is frontcourt insurance. Jalen Smith, still only 25, brings size and athleticism to Boston’s rotation. While his development has been uneven, he’s under contract for two more years on a team-friendly deal, making him a low-risk addition.
Then there’s Dalen Terry, who at 22 remains very much a project. His defensive tools are intriguing, but his offensive game needs work. Still, he could be a developmental swing for Boston — or a trade chip they could reroute for cap relief if needed.
Why the Bulls Might Do It
Chicago continues to hover in NBA limbo, somewhere between rebuilding and chasing the play-in. Adding Simons would give them a dynamic scoring option to pair with Josh Giddey in the backcourt.
As Forsberg put it: “Since no one ever knows what exactly the Bulls are doing, we’re calling them to see if they think Simons can help in their annual quest to land a play-in berth.”
Financially, the Bulls could absorb Simons without issue. For a team looking to add more scoring punch, the move could be appealing.
The Verdict for the Celtics
For Boston, this trade is less about talent than balance. Moving Simons’ $25 million deal for three smaller salaries would trim about $6 million, pushing them closer to slipping under the tax line. Dosunmu provides immediate value with his defense and versatility, while Smith and Terry offer upside at little risk.
The Celtics would be sacrificing a proven scorer, but they’d be gaining flexibility — the kind of move that gives Brad Stevens options later in the season. For a franchise juggling health, cap pressure, and championship aspirations, that flexibility might prove more valuable than Simons’ buckets.