TThe Boston Celtics are a month into their campaign and navigating a gap year without Jayson Tatum, but the calendar is now shifting toward the stretch when teams begin reshaping their rosters. Once a large portion of the league becomes trade-eligible on December 15, Boston is expected to be involved in discussions more than usual.
Fansided’s Matt Moore recently described the Celtics as “one of the more opportunistic teams” heading into trade season, noting that they continue to canvas the league for possibilities even while operating under tighter financial constraints.
That framing reflects where the Celtics stand today. After moving Kristaps Porzingis and Jrue Holiday this summer to dive under the second apron, Boston now has just one meaningful midseason salary slot: Anfernee Simons and his expiring twenty-seven million dollar deal.
And based on his first stretch in green, Simons may be as important to Boston’s trade flexibility as he is to the nightly rotation.
Celtics Still Trying to Unlock Simons’ Role
GettyAnfernee Simons was acquired by the Boston Celtics from the Portland Trail Blazers this offseason.
Simons came over from the Portland Trail Blazers with the reputation of an explosive scorer who could ease the burden on Jaylen Brown and Derrick White. Through the first month, the highs have been impressive and the lows have been difficult to navigate.
He is averaging 13.9 points while shooting 40.5 percent from the field and nearly 40 percent from deep. The production is there in spurts, but the impact has not been consistent. His 25-point first half against the Orlando Magic showed how dynamic he can be. His 12-minute outing in the win over the Los Angeles Clippers showed how quickly he can slide out of the rotation when the rhythm isn’t there.
Boston has tried to reduce his on-ball burden. He has been effective as a catch-and-shoot threat, leading the Celtics in efficiency on those looks. There have also been flashes of encouraging playmaking. But there are still nights when the ball sticks, the spacing shifts and his defensive limitations stand out.
This is where the Simons discussion transitions directly into Boston’s trade-season logic.
Celtics’ Trade Structure Revolves Around Simons’ Contract
Boston sits about four million above the first apron and twelve million above the tax. If the Celtics want financial flexibility or room to add a rotation piece without triggering harsher penalties, Simons’ expiring contract becomes their cleanest mechanism.
A trade involving him would almost certainly be financially motivated. It would be designed to adjust the roster around the margins rather than pursue a blockbuster deal. It would aim to improve balance, cost control and fit while keeping the core intact.
That framework is a large part of why creative multi-team concepts are surfacing.
The Three-Team Example That Shows Boston’s Path
GettyThe Los Angeles Clippers are 4-11 to start the season, and new Bradley Beal and Kawhi Leonard injury updates don’t signal a positive future.
On a recent “How ’Bout Them Celtics” episode, a theoretical structure involving the Celtics, Sacramento Kings and Clippers was proposed. It was not a prediction. It was an illustration of how Boston can operate with Simons as their primary movable salary.
The idea looked like this:
Celtics receive:
• Bogdan Bogdanovic
• Bradley Beal
Clippers receive:
• Zach LaVine
Kings receive:
• Anfernee Simons
• John Collins
For Boston, the structure would reduce salary commitments by roughly six million dollars, ease apron concerns and bring in a pair of veterans without sacrificing major draft assets. For Sacramento, two expiring contracts would create an early reset opportunity. For the Clippers, LaVine would represent a scoring swing without costing them more picks.
The specifics are less important than what the exercise reveals: if the Celtics act, it will most likely be through Simons, and it will most likely be in the middle tier of the trade market rather than the top.
Celtics May Already Have the Right Short-Term Approach With Simons
Until the front office makes a decision, Joe Mazzulla appears to have settled on a simple, clear strategy. Simons gets early minutes. If the offense flows and the shot is there, the minutes expand. If they aren’t, Boston closes with lineups that prioritize defense, passing and continuity.
Simons can still swing games with his scoring, but Boston cannot sacrifice structure on nights where the rhythm is off. This approach protects the team’s identity while still giving him opportunities to impact the game.
Final Word
The Celtics are in a flexible position, something they rarely were in previous seasons. They have a strong roster, a significant expiring contract and the ability to stay active when the trade window opens.
Simons could play his way into a stable, dependable role. He could also become the piece that helps the Celtics reshape the roster as they look ahead to the second half of the season.
Either way, Boston will be a team to watch as December 15 approaches.
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