The Boston Celtics did not expect to be here.
A season that was initially framed as a bridge year after Jayson Tatum’s season-ending Achilles injury has turned into a legitimate Eastern Conference push. Boston entered Wednesday at 18–11, good for third in the East, forcing the front office to reconsider how aggressively — or conservatively — it approaches the Feb. 5 NBA trade deadline.
Celtics’ Simons Trade Plan Comes Into Focus
At the center of that recalibration is Anfernee Simons, Boston’s biggest offseason acquisition and most flexible trade chip.
According to NBA insider Jake Fischer, the Celtics are now open to keeping Simons beyond the deadline — a notable shift for a team that had previously viewed him primarily as a salary-matching tool.
“The Celtics could opt to play things clean and simple and search for deals that offload the scoring guard’s $27.6 million salary to help Boston duck the luxury tax during Jayson Tatum’s gap year,” Fischer wrote in The Stein Line. “Boston, though, unexpectedly entered Tuesday’s play at 18–11 — good for third in the East. So imagine the Celtics turning Simons’ deal into a frontcourt contributor. Perhaps then the Celts could truly challenge the likes of Detroit and New York in a wide-open conference, even if Tatum stays sidelined for the entire season.
“Yet I must pass along that sources with knowledge of the Celtics’ thinking say Boston could very well elect to keep Simons, too. I’ve been told that they are willing to pay some level of luxury tax this season after the many millions they shed in the offseason by offloading Jrue Holiday and Kristaps Porziņģis.”
Simons’ Fit in Boston Remains Productive, If Modest
Simons has averaged 13.0 points, 2.3 assists and 2.1 rebounds in 29 games with Boston, providing perimeter shot creation and spacing in Joe Mazzulla’s three-point-heavy offense.
A career 38 percent three-point shooter and 14.9-point scorer, Simons has settled into a complementary role rather than the featured one he held in Portland. His production has been steady but not transformative — a reality that keeps him squarely in trade conversations.
Still, his contract makes him uniquely valuable. Simons is in the final year of a $27.7 million deal, allowing Boston to either pivot toward roster improvement or reduce payroll if necessary.
Celtics Previously Explored Simons Trades
GettyDay’Ron Sharpe of the Brooklyn Nets looks for a pass around Luka Garza of the Boston Celtics.
In November, HoopsHype’s Michael Scotto reported that Boston explored multiple trade scenarios involving Simons shortly after acquiring him, including talks with the Brooklyn Nets.
Scotto wrote that Boston and Brooklyn discussed “several trade scenarios” that eventually collapsed before the season began. Those talks occurred as the Celtics navigated the league’s new second-apron restrictions while reshaping the roster around Tatum’s injury.
The discussions were not limited to Simons. Scotto reported that Boston targeted Nets center Day’Ron Sharpe as a potential frontcourt solution. Although Boston could offer only a veteran minimum contract at the time, the team believed Sharpe could compete for a starting role.
Sharpe is averaging 7.1 points, 5.6 rebounds and 2.2 assists in 16.3 minutes backing up Nic Claxton in Brooklyn. Boston’s interest reflected a persistent weakness — interior depth.
Frontcourt Needs Remain a Factor
The Celtics have relied heavily on Neemias Queta, who is averaging 10.9 points, 7.9 rebounds and 1.2 blocks, but Boston lacks a consistent second interior presence capable of anchoring lineups defensively and on the glass.
That reality is part of why Simons remains movable if the right opportunity arises.
“I do suspect, though, that if Boston could somehow move Simons for a rotational upgrade and lower their tax bill in the process — or get out of that penalty zone altogether — that would check all of the boxes Brad Stevens’ front office could conjure up,” Fischer wrote.
Luxury Tax Looms, But Pressure Has Eased
Boston remains roughly $12 million over the luxury tax, but Scotto reported that the Celtics are not under pressure to dump salary unless the right deal presents itself.
That flexibility stems from significant savings already achieved by moving Holiday and Porziņģis, and from ownership’s willingness to absorb some tax if the team remains competitive.
Still, the Celtics have resisted attaching draft capital — particularly a first-round pick — simply to move Simons’ contract, limiting their ability to manufacture cap relief.
A Deadline Defined by Optionality
Boston’s trade deadline posture now reflects its unexpected success.
Rather than chasing salary relief or rebuilding assets, the Celtics are operating from a position of optionality — willing to stand pat, willing to improve, and no longer forced into retreat.
Simons embodies that choice.
Whether Boston ultimately keeps him, flips him for frontcourt help, or uses him to fine-tune the roster will shape how far this unanticipated season can go — and how the Celtics balance short-term competitiveness with long-term flexibility.
For now, the Celtics are no longer selling.
They are evaluating.
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