Why the Celtics' potential Anfernee Simons move could shock the NBA

The Celtics' best path forward might be to retain Anfernee Simons beyond this season.
Dec 7, 2025; Toronto, Ontario, CAN; Boston Celtics guard Anfernee Simons (4) dribbles the ball against the Toronto Raptors during the first half at Scotiabank Arena. Mandatory Credit: John E. Sokolowski-Imagn Images
Dec 7, 2025; Toronto, Ontario, CAN; Boston Celtics guard Anfernee Simons (4) dribbles the ball against the Toronto Raptors during the first half at Scotiabank Arena. Mandatory Credit: John E. Sokolowski-Imagn Images | John E. Sokolowski-Imagn Images

When the Boston Celtics acquired Anfernee Simons in the deal that sent Jrue Holiday to the Portland Trail Blazers, the focus was on whether his new team would flip him before the start of the current campaign. Now, the attention is on whether they'll do so by February's trade deadline.

However, there's a compelling case for not only keeping the sharpshooting veteran beyond this season, but then re-signing him in the summer.

When he arrived in Boston, it was necessary to be patient, giving him time to acclimate to his new role. Simons spent the last two years operating as the primary option on offense for the Trail Blazers. He had to figure out how to adapt to coming off the bench and being the sixth man.

On the heels of producing 23 points in a late-November win over the Orlando Magic, the Florida native conveyed his preferred approach and how his new role has forced him to adjust.

"Honestly, just keeping it simple," said Simons. "[In] previous years, that was kind of my thing. Just ease into the game and see how they guarded me, and then, kind of be more aggressive in the second half. Here, I don't have that much time to be able to ease into the game, and so, taking the opportunities that's there. Just being myself, aggressive, and also making the right plays as well."

The impact of Anfernee Simons's new approach

That shift in mentality has helped him maintain his efficiency while anchoring the second unit. Simons is a career 38 percent shooter from beyond the arc. Last season, he hoisted 8.5 threes and converted them at a 36.3 percent clip. This year, with fewer minutes and touches, he's launching 6.1 triples. However, he's knocking them down at a 36.7 percent rate.

The six-foot-three guard, who's shooting over 50 percent from inside the arc, is averaging 12.8 points in 23.5 minutes.

"We talk about depth, we talk about guys sacrificing and all that, I mean, there's no one that's done that more than him over the transition," said Joe Mazzulla after a 103-95 victory vs. the Indiana Pacers at TD Garden. "I thought he's handled it really well, and I think when he's aggressive for us, it makes us a little bit of a different team."

Simons is also making strides at the other end of the floor.

"Defensively, I've just been really impressed, like, he's picked up, he's made it hard," stated Brad Stevens during a media availability at the Auerbach Center earlier this month. "I think he's made great strides in the months he's been here on that end. And I'm a big fan. I like him a lot."

He isn't just pressuring the ball, but he's also utilizing his six-foot-seven wingspan to disrupt opposing offenses by producing 1.2 deflections per contest, per NBA.com.

He has played with commendable effort, backing up his vow to be more engaged defensively than he was in years past.

The case for keeping Anfernee Simons

The eighth-year veteran's buy-in on defense speaks to an individual who is proving to be a fit within an organization that rightfully places a premium on its culture.

Simons is adjusting well to the role of sixth man and could grow more impactful in the coming months. It would also be intriguing to see him working alongside Jayson Tatum. The threat he represents as a kick-out option, combined with his ability to initiate the offense and create off the dribble, would help lighten the load for a player returning from a torn Achilles.

It's a benefit he can provide to lineups that include one of Tatum or Jaylen Brown.

If the Celtics play out this season with Simons, they'll have his Bird Rights. That exception allows them to exceed the salary cap to re-sign him.

The 26-year-old guard is in line for a significant paycut from his expiring $27.7 million salary. The non-taxpayer mid-level exception is $14.1 million this season. If re-signing him at an average annual value of the price it reaches next year is realistic, that could be palatable to both parties.

And if it doesn't work out to the level they hoped, then they can trade him. They would have an easier time doing so at a reduced rate than on his current contract.

If Simons could sign for the same amount elsewhere but return to a starting role, that may be an opportunity he won't pass up. If the Celtics believe a deal in that range isn't a part of the best way to build their roster under this punitive collective bargaining agreement, then his stay won't reach a second season.

It's also possible that Boston already believes it's best to trade him for a center or at least invest what it would take to retain him in acquiring a player at that position.

The most obvious potential target in the former scenario is Ivica Zubac. However, it doesn't appear like the Los Angeles Clippers want to move him during the current campaign. It's also possible the Celtics prefer a different option. That includes the prospect of moving forward with the incumbent, Neemias Queta, remaining in the first unit. It's an opportunity the 26-year-old center is thriving with.

Another key part of the equation is who moves to the bench when Tatum returns. If it's Payton Pritchard, the case for keeping Simons takes a hit. However, if it ends up being Jordan Walsh, then holding on to the team's current sixth man carries more value.

What's clear, though, is that Simons is proving to be a fit in Boston. At his age and potential price tag, the best path forward for a franchise aiming for an immediate return to championship contention might include having him as their sixth man.

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