Celtics left with two-sided riddle after summer of change

The Boston Celtics may take their time trying to figure out what to do with Anfernee Simons.
Boston Celtics President of Basketball Operations Brad Stevens
Boston Celtics President of Basketball Operations Brad Stevens | Michael Reaves/GettyImages

Change has been a constant for the Boston Celtics throughout the summer of 2025. It was always expected with the team’s expensive roster placing them above the league’s second-apron line. Rotation staples Kristaps Porzingis (when healthy) and Jrue Holiday were offloaded in salary-shedding trades, while Boston wasn’t able to afford to keep free agents Luke Kornet and Al Horford.

The turnover has been so volatile that Georges Niang, who came as return in the Porzingis deal, has already been rerouted to the Utah Jazz. Niang’s secondary move further cut costs for the Cs, bringing them down to just $1.7 million above the first-apron threshold.

Since then, there’s been speculation that newly-acquired guard Anfernee Simons and his $27 million salary are safe, but that may not be the case. In fact, some believe he’ll be traded even if he survives the summer as a member of the Celtics.

“The expectation persists, furthermore, that Boston will continue to invite trade discussion involving Anfernee Simons from now through next season's trade deadline on Feb. 5 at 3 PM ET,” wrote NBA Insider Jake Fischer as part of the latest Steinline newsletter.

The Celtics are left with a weird, Anfernee Simons riddle to solve

Simons clearly doesn’t have much trade value. He’s a 26-year-old offensively talented guard who struggles on defense. In 2025, there are simply too many skilled backcourt players for front offices to give up assets for an exciting, yet flawed player like Simons.

Keeping him around could be fun for a Celtics team without serious expectations in the upcoming campaign. It’s very possible that Simons could explode for a few massive scoring nights and provide exciting moments for the fanbase.

But, what does that get Boston in the long term?

Maybe, with how terribly dry the free agent market has been, Simons would re-sign next summer on a team-friendly deal, but it’s tough to tell at this point.

In the case that they were to trade him, there’s a chance they’d benefit in the long run. If Boston found a deal that only required them to take back roughly $17 million, then they’d dive below the luxury-tax line and begin the two-year process of resetting the repeater tax penalties.

Of course, there’s no guarantee that it’ll be in the organization’s best interest to spend so little once Jayson Tatum returns from his ruptured Achilles tendon. They very well could push their chips back towards the middle of the table come summer 2026.

At the very least, it’ll be interesting to see how well Simons fits with the Celtics, should he still be in town on opening night. He’s had to be the offensive focal point for some bad Portland Trail Blazers teams over the past few seasons, and would have a significantly lighter burden playing next to Jaylen Brown and Derrick White.

The good news is that regardless of the direction Brad Stevens and the rest of the front office elect to take with Simons, there will be a silver lining for fans and media to cling to.