The NBA trade deadline is days away, and the Boston Celtics are facing an unanticipated conundrum after offloading some sizable contracts over the summer.
Boston acquired Anfernee Simons during the offseason in a deal that sent Jrue Holiday to the Portland Trail Blazers. This move, like the others the team made last summer, was fueled by financial flexibility rather than immediate contention. With Simons on a $27.6 million expiring contract, it was assumed that he would be flipped quickly.
What neither the Celtics nor their fans expected was that deciding whether to move him would become so difficult.
Simons has played his way into a pivotal role for the Celtics at the most important part of the season. As the deadline approaches, what Boston’s front office chooses to do with him won’t just be a statement on Simons as a player. It will signal how the organization feels about this season’s success and whether it is real or not.
Simons Remains a Trade Candidate, but Perhaps Not an Inevitable One
Through the first two months of the season, Simons’ departure felt inevitable. His transition from a high-usage lead guard in Portland to a sixth man in Boston was clunky, and despite visible scoring flashes, his impact wasn’t substantial.
Through the team’s first 20 games, he was one of only two Celtics in the consistent rotation with a negative net rating. His defense was the main culprit. He was frequently targeted, struggled to stay in front of ball handlers, and landed in foul trouble far too often.
Celtics head coach Joe Mazzulla is known for his low tolerance of defensive lapses. As proven by several recent draft selections, it takes consistent effort and improvement to enter Mazzulla’s circle of trust.
As the season progressed, his development on that side of the court began to stand out.
Speaking about Simons in November, Mazzulla said the message on offense was simple: “We want you to be yourself, especially offensively.” On the other end, he added, “I think he’s done a good job being committed to being better and physical and the things we need defensively… I can be better, we can be better, making sure he’s more comfortable” (h/t @CelticsCLNS).
Now, with the trade deadline approaching, he looks exactly that: comfortable.
Rounding the Corner
After early growing pains, Simons began rounding the corner in December. In the 29 games since Dec. 1, Simons has posted a 10.3 net rating. His minutes have increased, his fouling has declined, and his defensive baseline has stabilized.
With that foundation in place, his offense has flourished. He’s recorded his three highest-scoring games of the season since the beginning of 2026.
After pouring in 39 points in a comeback win over Miami on Jan. 15, Mazzulla praised Simons’ defensive growth as much as his offense.
“He’s taken it to another level with his defense,” Mazzulla said. “Tonight the glaring this is his offense, but to me, his physicality, defense, and coachability is just top notch,” (h/t @SleeperCeltics).
Simons’ Ascendance to a Key Role
Simons is doing far more than a short-term rental was expected to do. He’s an important contributor and part of the reason why the Celtics are winning.
Boston ranks second across the NBA in offensive rating this season at 120.7. They’ve been staggeringly successful despite losing a significant portion of their offensive infrastructure from last season. The team is counting on players stepping up into elevated roles, and Simons’ experience carrying offensive workloads has translated.
The Celtics have won all five of the games Simons has scored at least 25 points.
His most recent performance on Feb. 1 encapsulated his impact. After Boston stumbled out to a 12-0 deficit early, Simons came off the bench and ignited the offense. ‘The Anferno,’ as fans have endearingly dubbed his heat-check scoring, was on full display as he scored 11 points in the final 2.5 minutes of the first quarter, tying the game and providing a much-needed spark.
But the celebration came with hesitation. Boston doesn’t play another home game before the trade deadline — and that performance may have been Simons’ final one at TD Garden as a Celtic.
The Dilemma at Hand
Simons playing his best basketball now only makes the dilemma harder to stomach.
On one hand, his value may never be higher. On the other hand, his importance to the roster has never been clearer.
Since the beginning of 2026, Simons ranks second on the Celtics in total points scored (276), trailing only Jaylen Brown. As Derrick White and Payton Pritchard have struggled with efficiency in expanded roles, Simons has provided essential playmaking relief as a bench engine.
What Boston does next will reveal far more than just their opinion of Simons.
What Will the Decision Reveal?
The Celtics are tied for the second-best record in the East (31-18). In addition, they also own the third-best point differential in the NBA (+343). On paper, they look capable of making a deep run. The deadline will reveal whether the front office believes that, too.
The offseason’s cost-cutting moves were defensible when expectations were modest, and Jayson Tatum’s injury clouded the season. Trading Kristaps Porzingis for financial relief rather than on-court production was justifiable with major uncertainty at the time. Now, with Simons playing at his current level and the way he’s helping the Celtics compete, dumping him for minimal would send a very different message.
There are trade constructions that could flip Simons for a long-term piece, most likely a center, but doing so would come with short-term risk. Boston needs Simons’ scoring to sustain its current offensive level.
Ultimately, what the Celtics decide will reveal how much the front office believes in this season.
Is There a Win-Now Trade?
There may be a third path. As crucial as Simons is to the current operation, with Tatum not completely ruling out returning later this season, is it possible that Simons is traded for a piece that still complements this roster?
Rumors that the Celtics have inquired about an upgrade at center have circulated for months. Boston has made the most of its center rotation with Neemias Queta and Luka Garza stepping up and seizing the opportunity. Still, when it comes to picturing an NBA Finals matchup against the likes of Nikola Jokic, they’ll likely need reinforcements.
Boston could trade Simons and draft capital for a center on a contract beyond the 2025-26 season. Several of their rumored targets, such as Ivica Zubac, Nic Claxton, Daniel Gafford, and others, could even save them money while filling a potential long-term need.
However, if they were to do so, it would risk putting serious strain on the Celtics’ few offensive engines through the rest of the season. Brown already has the second-highest usage rate in the NBA. White and Pritchard are also averaging career-high usage rates. Even if Tatum returns, it is unrealistic to suggest he'd be in top form.
A complementary big man may be a better long-term fit, and perhaps even make some of the ball-handlers' lives easier this year when it's their turn to initiate. Still, it would leave Boston thin on offensive creators for this season. If properly executed, it could work. But one injury to any of their primary scorers could end their season.
Closing
Anfernee Simons wasn’t meant to be a long-term piece in Boston. He was a bridge, a scorer, and an asset.
Instead, he’s become something more: a contributor, a developmental success, and a reason why the Celtics are winning games they might not otherwise.
Whether the Celtics trade him or not won’t just determine their roster construction. It will tell fans how seriously the organization believes in this season — and whether this unexpected run is worth fully leaning into.
Just as suddenly as Simons worked his way into the hearts of Celtics fans, those fans may be bracing for another difficult goodbye.