As the NBA’s unofficial trade season kicks off following the Dec. 15 milestone, all eyes in Boston are on Anfernee Simons - and for good reason. The 26-year-old guard, who was brought in as part of a broader financial and roster reshuffling, has never quite found his footing with the Celtics. Now, with the trade window wide open and Boston firmly in the Eastern Conference mix, the question isn’t if Simons will be moved - it’s when, and for what.
Simons’ Fit - or Lack Thereof - in Boston
Let’s start with the obvious: Simons is a talented scorer. He’s averaging 13.1 points, 2.5 assists, and 2.2 rebounds in just under 24 minutes per game this season.
That’s solid production in a limited role. But the Celtics didn’t bring him in to be a sixth man microwave scorer.
He was part of a calculated move to create flexibility - both financially and on the floor.
Boston initially acquired Simons while moving off Jrue Holiday’s contract, knowing full well that Simons’ expiring $27.6 million deal would have value ahead of the trade deadline. But as the team has surged to third in the East and Jayson Tatum edges closer to full health, Simons’ role has only shrunk.
His 43.3% shooting clip is serviceable, but not enough to offset a defensive box score plus-minus that’s firmly in the red. On a team built around two-way play and defensive versatility, that’s a tough sell.
The Financial and Strategic Crossroads
Here’s where it gets tricky. The Celtics are in that delicate zone between long-term financial prudence and short-term championship ambition.
Some believed they’d try to dip below the luxury tax line, and that’s still on the table. But with the East wide open and the Celtics in striking distance, the temptation to make a win-now move is very real.
Simons’ contract is Boston’s best trade chip. It’s large enough to match salaries in a blockbuster, and it comes off the books this summer - a dream scenario for any team looking to clear cap space. That kind of flexibility could help Boston land a legitimate frontcourt upgrade, possibly a center who can pair with Neemias Queta and give the Celtics more size and rim protection heading into the postseason grind.
What Comes Next?
The league is on the cusp of a flurry of movement, with several teams in both conferences eyeing upgrades before the market gets too competitive. Boston has to decide whether it wants to be a buyer or a seller - or, more realistically, something in between. Either way, Simons will be central to whatever direction they choose.
If Tatum returns at full strength, the Celtics' need for a scoring guard off the bench diminishes even further. That puts added pressure on Brad Stevens and the front office to explore every option. Whether the goal is to shed salary, add a rotation-ready big, or stockpile future assets, Simons is the key that can unlock a variety of doors.
The Bottom Line
The Celtics are in the thick of the playoff race, and they have a real shot at making noise in the East. But they’re also staring down the reality that Simons is likely gone this summer - and not for nothing.
If Boston holds onto him past the deadline, they risk losing a valuable asset for zero return. That’s not a gamble a contending team can afford to take.
Yes, the financial side matters. Yes, it’s tough to make trades in today’s cap landscape.
But Boston’s front office has shown it isn’t afraid to make bold moves, and this is one of those moments where boldness may be required. Simons has value, and the Celtics have leverage.
Now it’s just about pulling the right strings.
Because in Boston, the goal isn’t just to stay competitive - it’s to hang banners. And if moving Simons helps get them one step closer, the time to act is now.