The Boston Celtics have endured a busy offseason, trading the likes of Kristaps Porzingis and Jrue Holiday after recently winning the 2024 NBA Finals. One of the players Brad Stevens added to his roster by trading away the two former All-Stars was Anfernee Simons, but now there are questions about whether he will begin the 2025-26 season with Boston.
The word that best describes this offseason for the Celtics is “change.”
Aside from their massive roster changes and overhaul around Jayson Tatum, Jaylen Brown, and Derrick White, the C's saw long-time owner Wyc Grousbeck officially hand over duties to new owner Bill Chisholm.
Since Tatum is expected to miss a vast majority of the 2025-26 season (if not all) rehabbing his Achilles injury, it was in Stevens' and the organization's best interest to cut their massive tax bill and move out of the tax aprons.
That is why Porzingis and Holiday were traded, as well as Georges Niang, whom the team acquired in their three-team Porzingis trade with the Atlanta Hawks.
Simons was acquired by the Celtics in their trade with the Portland Trail Blazers, and he is a young combo guard who can immediately make a difference as another perimeter shooter for head coach Joe Mazzulla to experiment with.
However, Simons' name has surfaced in trade rumors this offseason since the Celtics added him in June.
The Celtics are still about $4 million above the first apron and $12 million into the luxury tax, which is why moving Simons and bringing back fewer salaries could be beneficial to the team's cost-saving plan this offseason. Then again, Simons is still only 26 years old and on a $27.6 million expiring contract.
While Simons' name continues to come up in rumors around the league, there are reasons for the Celtics to wait on this decision before the 2025-26 season.
The value Anfernee Simons can present to Celtics
Over the last handful of seasons, the Celtics have been right at the top of the Eastern Conference as legitimate title contenders. That won't be the case during the 2025-26 season, as Stevens and the front office are basically hitting the reset button and conducting early evaluations as to what the roster will look like for the 2026-27 season.
Even though the Celtics will remain competitive and are not entirely tanking this upcoming year, it's clear that they are no longer a part of the upper echelon of teams in the championship mix without Tatum.
As a result, players like Payton Pritchard, Sam Hauser, and Anfernee Simons all have a great opportunity to prove their worth in elevated roles.
In Simons' case, he joined Boston after spending the first seven years of his career in Portland. Last season, he averaged 19.3 points and 4.8 assists per game while shooting 36.3 percent from 3-point range and making 215 triples in 70 games.
If he were on the Celtics' roster, Simons would've ranked fourth in total threes behind White, Tatum, and Pritchard.
Mazzulla has put a point of emphasis on his team shooting more perimeter shots over the last two years, which is why Simons is the ideal player for the Celtics to take a chance on. After all, the worst thing that happens is that things don't work out, and he becomes a free agent in 2026.
The Celtics made this trade involving Holiday for Simons with the mindset of creating options for themselves, and as a result, they can continue to gauge potential interest in the young guard now through the trade deadline in February.
Over the last several weeks, the Celtics have continued to put out feelers to teams that have shown past interest in the young guard to get a sense of what his market currently looks like and could shape up to be before the trade deadline in February, sources said.
Although it doesn't appear as if a trade is on the horizon before training camp, this has not stopped Boston from exploring potential paths to a deal involving Simons.
Other than remaining competitive and finding ways to continue cutting costs, the Celtics' other main goal is to maintain financial flexibility. If they were to make a trade, Boston wouldn't want any long-term salary, which is another reason why holding onto Simons to begin the season makes the most sense.
However, the Celtics' main reason for not trading Simons right now is the fact that he could end up being a diamond in the rough for them.
In Portland, Simons was tasked at a young age with being the team's main offensive weapon, and he, for the most part, succeeded in this role. Now that he is the third- or fourth-best scoring option in Boston, Simons could unlock a whole new path in his career, one where he becomes one of the leaders in three-point shooting across the league.
Since he is on an expiring deal, the Celtics have no need to rush into a trade unless they are receiving unthinkable value. More teams will express interest in Simons as the season goes on and players end up getting hurt, which is why his value will only increase before the trade deadline.
This is especially true if he finds a lot of success as an efficient three-point shooter in Mazzulla's offensive plans.
Looking ahead past the trade deadline, perhaps there is even a path to the Celtics holding onto Simons and seeking to sign him to a smaller contract next offseason to get back to their championship ways.
Simons is just now reaching the prime years of his career, and the Celtics have a chance to get a really strong look at him before he hits unrestricted free agency.
