Anfernee Simons’ arrival in Boston was always going to raise questions. Acquired in the offseason deal that sent Jrue Holiday to Portland, Simons came in as a dynamic scorer with a reputation for creating his own shot-something the Celtics haven’t always had in abundance off the bench. But as we approach the trade deadline, his role in Boston’s long-term plans is looking more like a question mark than an exclamation point.
Simons is in the final year of a four-year, $100 million contract. That alone makes him a potential trade chip for a Celtics front office that’s always thinking a few moves ahead.
With the Feb. 5 deadline looming, the logic is simple: if you don’t see him in your playoff rotation, and you’re unsure about re-signing him this summer, it makes sense to explore what he could fetch on the market now. Letting a player walk for nothing is rarely part of Brad Stevens’ playbook.
And while Simons has carved out a solid role in Boston’s second unit, his long-term fit-especially in the postseason-remains murky. Through 29 games this season, all off the bench, Simons has been a consistent scoring presence, averaging 13 points, 2.1 rebounds, and 2.3 assists per game.
He’s shooting 43.1% from the field and knocking down nearly 37% of his threes. On paper, that production is valuable.
But this isn’t just about numbers-it’s about how those numbers translate when the game slows down and every possession matters.
That’s where concerns start to creep in. According to advanced metrics from DunksandThrees, Simons ranks in the bottom 10th percentile among guards in Defensive Estimated Plus/Minus.
That’s a red flag for a team with championship aspirations. In the playoffs, where matchups are hunted and weaknesses are exposed, defensive liabilities can be costly.
And with Derrick White and Payton Pritchard both earning the trust of the coaching staff-and playing significant minutes-it’s hard to envision a scenario where Simons is logging heavy postseason minutes unless something changes dramatically.
ESPN’s Tim Bontemps echoed that sentiment recently, suggesting that Simons may not be a major factor in the playoff rotation regardless of whether he’s still on the roster. The Celtics, after all, have built their identity on defense and versatility. Simons brings scoring, yes, but he doesn’t offer the same level of two-way impact that Boston typically leans on in high-leverage moments.
Still, moving Simons isn’t a simple plug-and-play decision. Trading him would thin out Boston’s guard depth, and that’s not something the front office takes lightly. If the Celtics do decide to deal him, it’s likely they’d need to make additional moves to shore up the backcourt and maintain the balance that’s been a hallmark of their roster construction this season.
So where does that leave things?
For now, Simons remains a valuable scoring option off the bench-someone who can come in, create offense, and give the starters a breather. But as the deadline inches closer, Boston will have to weigh whether that value is best utilized on the court or as a trade asset. It’s not just about what Simons brings now-it’s about what his presence (or absence) means for the Celtics’ title push in April, May, and, they hope, June.
The next few weeks could be pivotal. Whether Simons stays or goes, the Celtics’ decisions will be shaped by one thing: maximizing their championship window. And in that context, every move matters.