The Boston Celtics have fully committed to restructuring their finances to permit a more flexible retooling around Jaylen Brown and Jayson Tatum in 2026. It's an admittedly logical approach given Tatum's recovery from a ruptured Achilles tendon and the limitations that inevitably places on the team's potential.
The most likely player to be traded to facilitate that mission is Anfernee Simons—a truth the Celtics should seriously reconsider.
Boston acquired Simons in a one-for-one trade for fan favorite Jrue Holiday. It was an intriguing move on several levels, as Simons is a younger guard with a well-rounded skill set as a scorer that could potentially help the Celtics fill a portion of the scoring void Tatum's injury has created.
According to Jake Fischer of The Stein Line, that simply may not be Boston's priority, as it plans to continue fielding trade offers for Simons until the 2026 deadline.
"The expectation persists, furthermore, that Boston will continue to invite trade discussion involving Anfernee Simons from now through next season's trade deadline on Feb. 5 at 3 PM ET."
For as valid as it is to explore the interest that may exist externally, it would behoove the Celtics to first prioritize determining if Simons fits alongside Brown and Derrick White.
Anfernee Simons is too talented to simply write off as a trade piece
Simons is a 26-year-old scoring guard who has steadily developed into one of the more productive players south of the All-Star line. Over the past three seasons, he's accumulated averages of 20.7 points, 4.7 assists, 2.9 rebounds, and 3.3 three-point field goals made on .434/.374/.904 shooting.
Unfortunately, Simons hasn't played a minute of postseason basketball since 2021—a concerning truth that's admittedly a bit misleading.
Portland began the 2024-25 season at 13-28—the type of record that all but guarantees an absence from the postseason. It went 23-18 the rest of the way, however, and Simons played a significant role in the team's success.
During that time, Simons averaged a team-high 20.5 points per game, thus proving to be capable of contributing to winning basketball in a high-volume role.
In Boston, Simons will have the benefit of playing alongside a more veteran-heavy cast of players—many of whom won a championship together in 2023-24. That includes the trio of Brown, Payton Pritchard, and White, who have all established themselves as reliable sources of offense.
That could prove to be the impetus to an increase in all-around efficiency from Simons, who has already shot 42.7 percent or better on catch-and-shoot threes in two of the past four seasons. He's also coming off of a 2024-25 campaign in which he averaged 6.1 points via drives per game on 47.0 percent shooting.
Defensively, Simons has the physical attributes to perform at a higher level than he has thus far with a 6'9.25" wingspan and ideal athleticism. He's admittedly never turned heads on defense, but this could be a golden opportunity for him to rewrite his career narrative and secure a long-term future in Boston.
It's understandable for the Celtics to peruse the trade market, but they must be sincere in their effort to evaluate how Simons fits in Boston before giving up on him too soon.