Anfernee Simons was the most fascinating member of the 2025-26 Boston Celtics before the season. He was acquired in the Jrue Holiday trade, mostly to reduce the team's salary obligations, both this season and going forward. His $27.6 million expiring salary gave the Celtics optionality in the future. They could trade him before the deadline, re-sign him to a lower amount in the offseason, or let him walk in free agency for more financial relief.
How Simons would start the season would be the biggest determining factor in general manager Brad Stevens' decision. Through the first 20 games of the season, Simons has been as advertised. He has been fine as a shot creator and shot maker, but hasn't been a true difference-maker. If anything, he has had a smaller-than-expected role, not starting a single game, and only playing 24 minutes per game, averaging 13.7 points, 2.6 assists, and 2.2 rebounds with .447/.407/.844 splits.
But even if he's playing well, it's hard to imagine his being on Boston's roster for much longer after December.
Anfernee Simons Remains the Most Likely Celtic to Be Traded
This makes Simons less likely to be a part of the Celtics going forward. With Payton Pritchard, Derrick White, and Jaylen Brown carrying the offensive burden, there isn't much room for an offense-only guard who makes $27 million. Upon Jayson Tatum's return, there will be even less use for Simons' offense. The Celtics will need size, athleticism, and off-ball ability more than the on-ball creation and pick-and-roll chops that Simons has.
The Celtics have a ton of options at the trade deadline. It's not yet clear whether they would be more interested in buying or selling. They have the draft capital to attach next to matching salary (aka Simons) to target starting-caliber players who may be on the trade block. Whether Stevens will pursue this route will likely depend on who will be available on the market.
If there is an impactful player who fits the team's on-court needs and long-term salary structure better, the Celtics will almost certainly try to use Simons' contract to acquire him. Stevens leaves no stone unturned. He aggressively looks for any deal that could add value, even on the margins. The Celtics will continue to prioritize next season as they have more of a chance to be a contender when Tatum is back in the 2026-27 NBA season.
It's hard to imagine Simons having a role on the next great Celtics team. Instead of losing him for nothing, the Celtics would be wise to move on from him, regardless of the return package.