The Boston Celtics have been active behind the scenes, working the phones and exploring ways to fine-tune their roster - and one name that’s been at the center of those conversations is Anfernee Simons.
According to recent reports, the Celtics and Brooklyn Nets held multiple discussions over the summer centered around Simons, with the idea of rerouting the talented guard to Brooklyn. While nothing materialized, the talks signal that Boston is open to reshaping parts of its roster, especially if it means getting value for a player on an expiring deal. The Milwaukee Bucks were also reportedly monitoring Simons’ situation, which speaks to the league-wide interest in the 26-year-old.
Boston's interest didn’t stop with Simons. They also kicked the tires on Day’Ron Sharpe in free agency.
The Celtics were intrigued by the 6-foot-11 big man and were willing to offer him a shot at competing for the starting center spot. The catch?
Boston could only extend a veteran minimum offer - a tough sell for a player still in his prime and coming off five seasons with the Nets.
There’s still a chance that the Celtics and Nets revisit a potential swap involving Simons and Sharpe before the February trade deadline. But if that scenario comes back to life, Boston will need to tread carefully - especially when it comes to the financials.
One name that’s been floated as part of potential trade packages is Terance Mann. And while the idea of bringing the Lowell, Massachusetts native back home might tug at the heartstrings, it’s a move Boston should avoid.
Here’s why: Mann is a solid two-way contributor and gives you that switchable wing defense every contender craves. But his contract is far from ideal.
He’s earning $15.5 million this season, with two more years on the books at $15.5 and $16 million, respectively. That’s a lot of money for a role player - especially when you’re already navigating the luxury tax and trying to maintain roster flexibility.
Simons, on the other hand, is on an expiring $27.7 million deal. That makes him a more attractive trade chip, not just for his scoring punch off the bench, but also for the cap relief he could provide in the offseason.
If Boston doesn’t see him as a long-term fit - or if they’re wary of the price tag it might take to keep him - moving him before the deadline makes sense. But taking back long-term salary in the process?
That’s where things get tricky.
To Simons’ credit, he’s handled a tough transition with maturity and professionalism. After spending the past two seasons as Portland’s go-to scorer, he’s now coming off the bench in Boston - a shift that takes time to adjust to, both mentally and stylistically.
“It’s for sure an adjustment,” Simons admitted after a recent 138-129 win over the Magic. “The past couple years, when you started, and teams are guarding you aggressively from the jump. And so now, you’ve got to take your time and read the game and see how the best way you can attack it.”
In Portland, Simons had the luxury of feeling out the game - figuring out how defenders were playing him and then ramping up the aggression in the second half. That’s not an option when you’re coming off the bench. Now, it’s about staying ready and striking quickly.
“Here, I don’t have that much time to be able to ease into the game,” Simons said. “So, taking the opportunities that’s there.
Just being myself, aggressive, and also making the right plays. I think simplifying that way, it’s been easy for me the past couple games.”
That mindset is starting to pay off. Simons dropped 18 points in a gritty 117-115 win over the Cavaliers - arguably one of Boston’s most hard-fought victories of the season. He’s showing that he can still be a difference-maker, even in a reduced role.
But the bigger picture looms. Simons is a talented scorer and a valuable piece, but if Boston doesn’t plan on re-signing him, his expiring contract becomes a trade asset. The key will be finding the right return - one that doesn’t saddle them with long-term salary or compromise their flexibility moving forward.
The Celtics are in the thick of the title hunt, and every roster move from here on out has to be made with that goal in mind. Trading Simons could make sense.
Acquiring Sharpe could help. But bringing in a contract like Mann’s?
That’s a move that could haunt them down the line.