The Boston Celtics are entering a pivotal offseason following a disappointing playoff exit, and the front office is leaving no stone unturned in their pursuit of roster upgrades. While much of the attention has centered on frontcourt additions and potential blockbuster trades, a surprising name has emerged as a compelling internal solution: Anfernee Simons.
According to Boston Herald reporter Zack Cox, the Celtics could seriously consider bringing back the dynamic guard they traded away at the deadline, setting the stage for a high-stakes reunion that could reshape Boston’s backcourt.
“Speaking of reunions, would the Celtics consider bringing back Simons for a more substantial stint?” Cox wrote. The former Trail Blazers starter proved to be an effective sixth man during his brief half-season in Boston, scoring in double figures in 37 of his 49 appearances, shooting a respectable 39.5% from three-point range, and earning consistent praise from head coach Joe Mazzulla for his improved defensive effort.
Simons’ Second Trial in Green
Simons arrived in Boston last summer as part of the trade that sent Jrue Holiday to the Portland Trail Blazers in exchange for the young guard and two second-round picks. Though he had developed into a high-volume starter in Portland — averaging 19.3 points per game in the 2024-25 season following back-to-back 20-point campaigns — his role in Boston was that of a high-impact bench contributor.
In 49 games with the Celtics, Simons averaged 14.2 points per game off the bench. However, Boston’s subsequent search for frontcourt size led them to trade Simons to the Chicago Bulls at the deadline in a deal centered around veteran center Nikola Vucevic. The move helped the Celtics shed salary and drop below the luxury tax line, but Simons appeared in just six games for the tanking Bulls before being shut down for the season.
Now 26 years old, Simons is expected to command significantly less than the $27.7 million he earned in the final year of his current contract, potentially opening the door for a more team-friendly deal that could still approach nine figures over multiple seasons if Boston commits long-term.
The Brown Factor and Backcourt Dynamics
The timing of a potential Simons reunion is particularly intriguing given the current uncertainty surrounding Jaylen Brown. The 29-year-old superstar has been the subject of persistent trade rumors following Boston’s early postseason departure. Should the Celtics pursue a major star like Giannis Antetokounmpo or another high-profile target, Brown’s departure would immediately create a significant void in the wing and guard rotation.
Currently, the backcourt is anchored by starting point guard Derrick White and backup Payton Pritchard. While Baylor Scheierman provides solid depth, he lacks the proven scoring punch and playmaking ability Simons has demonstrated at the NBA level. A return to Boston could give Simons a chance to carve out a larger role — potentially as a key spark plug off the bench or even a starter in certain lineups — while providing the Celtics with a familiar, high-upside talent who already understands Mazzulla’s system.
Simons’ ability to score off the dribble, create for teammates, and stretch the floor with his shooting would add valuable versatility to a backcourt that, even with its current stars, could benefit from additional firepower and youth.
A Calculated Reunion?
From a roster construction standpoint, the original decision to move Simons made sense in the moment: acquiring size and managing the luxury tax were priorities. However, with Boston now exploring multiple frontcourt options in free agency and the draft, the Vucevic acquisition appears less impactful in hindsight, especially if the team ends up addressing the frontcourt through other avenues.
A Simons reunion would represent a low-risk, high-reward move for a Celtics team that values familiarity and player development. At 26, Simons remains on an ascending trajectory, and his previous stint in Boston showed he can thrive in a winning environment when given the right opportunity.
As the NBA offseason heats up, all eyes will be on how the Celtics navigate the Jaylen Brown situation and whether they decide to roll the dice on a familiar face who could provide exactly the kind of scoring depth and guard versatility they may soon need. A $100 million-level commitment would be bold — but in a contending window, calculated aggression often separates the good from the great.