Six months ago, when the Boston Celtics acquired Anfernee Simons from the Portland Trail Blazers, the pairing came with an expected expiration. No matter how well he fit, moving on from Simons and his $27.7 million expiring contract always loomed, and that reality arrived abruptly less than two days before Thursday’s 3 p.m. ET NBA trade deadline.
Boston reportedly pulled the trigger on a trade, sending Simons to the Chicago Bulls in exchange for center Nikola Vučević just hours before facing Cooper Flagg and the Dallas Mavericks on Wednesday night. The move immediately forced adjustments, as coach Joe Mazzulla reworked the rotation by replacing Simons — the team’s leading bench scorer — with Payton Pritchard, the reigning Sixth Man of the Year, while also elevating second-year guard Baylor Scheierman into the starting lineup.
Whether it was in the offseason before Simons ever suited up in Celtics green or within the final 48 hours before the deadline, a departure always seemed inevitable. The front office spent much of the summer restructuring the roster to reduce luxury tax penalties, making it unlikely that Simons, regardless of performance, would convince Boston to keep him past the deadline, let alone consider an extension. None of this was new information, but even with the awareness that a departure was likely, parting ways with Simons remains a sensible business move that will still be felt.
Simons was moved out of a starting role in Portland and into a bench role in Boston, logging fewer minutes and taking fewer shots than last season. With the roster gutted and Jayson Tatum less than two months removed from surgery to repair a ruptured right Achilles tendon, there was no guarantee his reduced role would translate into helping turn the underdog Celtics into a legitimate contender. Still, he treated it as an opportunity for growth and development, and that’s exactly what he made of his 49-game stint.
BOSTON, MA - JANUARY 5: Anfernee Simons #4 and Hugo Gonzalez #28 of the Boston Celtics high five during the game against the Chicago Bulls on January 5, 2026 at TD Garden in Boston, Massachusetts. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2026 NBAE (Photo by Brian Babineau/NBAE via Getty Images)
BOSTON, MA - JANUARY 5: Anfernee Simons #4 and Hugo Gonzalez #28 of the Boston Celtics high five during the game against the Chicago Bulls on January 5, 2026 at TD Garden in Boston, Massachusetts. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2026 NBAE (Photo by Brian Babineau/NBAE via Getty Images)
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Never once did the organization need to question Simons’ commitment toward buying into Mazzulla’s vision.
Understanding the rationale for swapping Pritchard out for Simons in the sixth man role wasn’t difficult for him. The Celtics needed depth, and inserting an elite, high-volume shot creator who could make plays for others didn’t just make sense — it worked. Simons was impactful, steadily improving, and a low-maintenance teammate. The team never had to worry about his ego taking over, because even though everyone knew he was capable of starting upon arrival, his role didn’t diminish his contribution to helping the Celtics reach the No. 2 seed in the Eastern Conference before he was traded to Chicago.
He embraced the culture that awaited him in Boston and appreciated everything that came with it.
“The fans are so into the game,” Simons said while guest appearing on the White Noise Podcast last week. “You go to other places, and they’re fans of the team, but they’re not invested in the game of basketball like they are here (in Boston). Last game, during the National Anthem, I was just paying attention to how many people were in the crowd. The arena was packed all the way to the top level — flooded with people. It’s crazy, because you don’t experience anything like that anywhere else.”
Simons had an attitude that embodied everything the Celtics could’ve asked for — and then some. He was selfless, yet knew exactly when the moment called for him to take over. He played off the bench, but his contributions were those of a starter. And in his final game with the team, he scored 27 points on 10-of-18 shooting, knocking down six threes in one last effort to make his case for staying. The home crowd at TD Garden responded with a thunderous ovation, fully aware that they might have just witnessed the end of Simons’ time in Boston.
The qualities Simons brought with him every day in a Celtics uniform make moving on difficult — albeit possible. Teammates and coaches had nothing but glowing things to say about him all season, and for good reason. He turned a reduced role into his bread and butter. His 694 total points were third, only behind Naz Reid and Jaime Jaquez Jr. for the most bench points scored this season, yet he outpaced them both in 3-point percentage (39.5%) and with fewer turnovers (55), giving him a strong case for this season’s Sixth Man of the Year.
His demeanor, especially from a player who had just averaged a career-high 19.3 points in 70 starts the year prior, can’t be overstated.
In Chicago, Simons will likely reclaim a starting role and have the opportunity to thrive and build a case for the kind of contract his talent deserves in free agency. His time in Boston, though brief, will be remembered fondly by the organization, his former teammates, and the fans for years to come.
Anferno earned that.