The Boston Celtics have engineered one of the most dramatic roster overhauls in recent memory. Championship pieces scattered. Financial flexibility prioritized. A franchise-altering injury forcing an entire season into question. Yet according to league insiders, Boston’s transformation may be far from over.
Why Are the Celtics Still Shopping Anfernee Simons?
According to NBA insider Jake Fischer, Boston continues to evaluate potential deals for guard Anfernee Simons, who only recently arrived via the Jrue Holiday trade. Speaking on the NBA Insider Notebook with Jake Fischer, he revealed:
“The Celtics, to my understanding, are going to continue to look for salary-shedding opportunities, and they are going to continue to listen to incoming trade calls for Anfernee Simons.”
Simons, 26, carries an expiring $27.7 million deal, making him an attractive asset for contenders seeking proven shooting depth. However, for Boston, the calculus has shifted dramatically. With Jayson Tatum sidelined for most, if not all, of the upcoming season, the franchise has effectively written off 2025 as a reset year.
This reality has fundamentally altered Boston’s approach. Rather than chase immediate wins with a depleted roster, they’re prioritizing financial flexibility and future positioning. Shedding Simons’ substantial salary could serve both goals while adding valuable draft capital or younger assets.
President Brad Stevens has already dismantled much of last season’s championship-contending roster. Jrue Holiday and Kristaps Porziņģis were dealt in separate moves, while veteran stalwarts Al Horford and Luke Kornet departed in free agency. These moves represented more than roster turnover – they signaled a complete philosophical shift.
In their place, the Celtics added cost-effective options like Chris Boucher, Luka Garza, and Josh Minott. While these signings helped Boston duck under the dreaded second tax apron, their work toward financial relief remains incomplete.
Moving Simons could help the Celtics avoid even the first luxury-tax line, saving millions while resetting their repeater-tax clock. Given that Boston’s championship window is effectively paused while Tatum recovers from a ruptured Achilles, the decision to prioritize financial flexibility over short-term competitiveness makes strategic sense.
What Trade Scenarios Could Reshape Boston’s Future?
Bleacher Report outlined one potential three-team framework involving the Toronto Raptors and Brooklyn Nets. In this scenario, Boston would send Simons to Toronto, a franchise desperate for shooting after ranking near the bottom of the league in three-point production.
The proposed deal would see Toronto part with RJ Barrett, while Brooklyn would act as a facilitator, acquiring Barrett and sending Terance Mann to Boston. The Nets would also contribute additional salary-matching pieces to make the trade work financially.
For Boston, this type of framework offers dual appeal. They would significantly lower their payroll while acquiring younger wings like Mann and potentially Ochai Agbaji, plus securing future second-round draft capital. Such a deal wouldn’t vault the Celtics back into immediate contention, but it would align perfectly with their apparent strategy of maintaining financial flexibility while accumulating assets.
The appeal extends beyond just money. Mann, at 28, represents the type of versatile wing who could complement Boston’s core when healthy. His defensive versatility and improved three-point shooting would provide valuable depth without requiring significant financial commitment beyond this season.
Additionally, any deal involving Simons would likely net Boston at least one future draft pick, continuing Stevens’ focus on asset accumulation during this transitional period.
Whether or not a Simons trade materializes before the season begins, the underlying message remains crystal clear. The Celtics have embraced transition mode. Without Tatum anchoring their championship aspirations, the focus has shifted from immediate titles to strategic positioning for future success.