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Jaylen Brown, Boston Celtics

The Boston Celtics like most contending teams will look into the free agency market for players that can improve the roster. 

Scouring the free agency market for the right fit isn’t always easy. But someone who is a familiar face could make it easier.

According to Boston Herald reporter Zack Cox, one intriguing option could be guard Anfernee Simons, whom they traded away at the deadline.

“Speaking of reunions, would the Celtics consider bringing back Simons for a more substantial stint?” Cox wrote. “The former Trail Blazers starter was an effective sixth man during his half-season in Boston. He scored in double figures in 37 of his 49 appearances, shot 39.5% from 3-point range, and drew frequent praise from [head coach Joe] Mazzulla for his improved defense.”

Simons arrived in Boston just last summer and became a role player before being moved mid-way into the season. A potential reunion might make sense seeing how the months after the trade have played out.

Simons’ and the Celtics’ Second Trial

GettyBoston Celtics guard Anfernee Simons looks on. (Photo by Nic Antaya/Getty Images)

Simons was part of the deal that saw Boston trade Jrue Holiday to the Portland Trail Blazers in exchange for the young guard and two second-round picks. It wasn’t so much of a like-for-like player exchange but the deal happened.

Simons had developed into a starter for Portland and a high-scoring one as well. He averaged 19.3 points per game in the 2024-25 season. This was on the back of two 20-point average seasons.

Coming into Boston, a starting role wasn’t always expected but Simons played a solid role off the bench. In 49 games he averaged 14.2 points per game. Yet, the Celtics, searching for a center, traded him to the Chicago Bulls in a deal for veteran center Nikola Vucevic.

“The Celtics shipped Simons to Chicago at the NBA trade deadline — a move that netted them Vucevic and helped them drop below the luxury tax line — and he played in just six games for the tanking Bulls before being shut down for the season,” Cox added. “The 26-year-old likely will need to settle for less than the $27.7 million he earned in the final year of his current contract.”

At the time, the move made sense from a Boston point of view. It shed salary and dropped below the luxury tax line while adding frontcourt size. However, it was surprising at the same time because the Celtics took a guard who was on an ascending trajectory in Portland and didn’t utilize him. 

Also, Boston is now linked with several front-court options which makes the Vucevic deal look meaningless roster-wise. 

Guard Depth and Fit for Simons in Boston’s Backcourt

The Celtics are still anchored by their more established stars especially in the backcourt. With Jaylen Brown leading in the guard position and having an elite two-way game, it makes it hard for any guard to slot in and have consistent starting minutes.  

But Brown, 29, finds his name drenched in trade rumors after the Celtics’ disappointing playoff exit. If Brown gets moved this summer for a big-hit star like Giannis Antetokounmpo, the Celtics could immediately have need for another guard.

Derrick White is the starting point guard and behind him is Payton Pritchard. That position is already locked. This crowded hierarchy didn’t give Simons a start when he played in Boston.

Simons may have been a starting guard in some other franchise not named the Celtics. But a reunion could come at a perfect time for him. Boston’s depth for Brown is Baylor Scheierman, a good squad piece but compared to Simons, might be lower on the pecking order.

Simons has proven that he can score and create and will massively improve Boston’s back court.