Celtics Getting More Clarity on Potential Trade Piece Anfernee Simons

The Boston Celtics destroyed the Chicago Bulls on Monday night at the TD Garden, 115-101, and they had two 20-point scorers in the process. Shockingly, neither was the red-hot Jaylen Brown, who, with 14 points, scored below 20 for the first time since November. Brown had an off-night from the field, making just six of his 24 shot attempts.

No, the top scorers were Payton Pritchard (21) and Anfernee Simons (27). Simons made eight of his 14 threes and was the second unit spark that bailed out bad shooting nights from Brown and Derrick White (3/15, 1/10 3-PT). He was timely with his shot-making and moved the ball well, though he was a bit turnover-prone, with three for the game.

Unquestionably, Boston couldn't have won without Simons. His 27 minutes, the fourth-highest on the team after Brown, White, and Pritchard, were game ball-worthy.

Now, the Celtics have questions about what to do with him. While trading him seemed like the move back when his shot wasn't falling in early December, his scorching January (19/37, 17/29 3-PT), which has coincided with a 3-0 record in the 2026 calendar year, throw doubt into that.

Anfernee Simons Making a Case to Stay on Celtics Past Trade Deadline

January was always going to be a test for Simons' fit in Boston, and so far, he's passing it with flying colors. With the team looking to stay in contention upon Jayson Tatum's return, Simons is making the case that he can't be replaced by any internal options. No external option can replace the time spent in Joe Mazzulla's system to this point, anyway.

What started as the only way to facilitate the Jrue Holiday trade with the Portland Trail Blazers has turned into the solution for the Celtics' second unit. Boston may have struck gold with Simons, which is funny considering he was almost traded before the season started. There was a worry that Simons could hinder any tanking efforts, but it turned out that he was a good culture fit on a team that only has intentions of winning.

Where Simons ends up long-term is an intriguing question. It's unclear if he'll get a raise from his $27 million expiring deal. Brad Stevens may not be interested in paying that, since Tatum's return could theoretically send Pritchard back to the bench in Simons' role.

Either way, it feels like Simons' free agency question could be one we're all asking past February 5, the more the guard plays like he's been to ring in the new year.