Anfernee Simons is smooth with the ball in his hands. He has proven himself as a big-time shot maker. He will likely fill up the basket next season.

He just might do that somewhere away from Boston.

Looking to continue shedding salary, the Celtics have explored the idea of flipping Simons’ $27.7 million expiring contract, according to league sources. In such a move, they would be aiming to accomplish two organizational directives Brad Stevens emphasized after the first round of the NBA Draft on Wednesday: regaining more roster flexibility and setting up a path to retain free agents Luke Kornet and Al Horford.

Even after offloading the contracts of Jrue Holiday and Kristaps Porziņģis in a pair of trades this week, the Celtics have significant work left to do if they aim to escape the luxury tax entirely. At the moment, they appear hopeful of accomplishing that goal, which would help them initiate the process of resetting the repeater tax. Though they currently sit about $15 million above the luxury tax threshold, they would need to cut more salary than that to position themselves far enough under the threshold also to afford to keep Kornet and Horford. Stevens, who called the veteran big men “huge parts of this organization” on Wednesday night, has stated he would like to re-sign both players.

Speculation has surrounded Sam Hauser’s future because it likely wouldn’t be difficult to find a taker for his four-year, $45 million contract (which would also fit inside another team’s non-taxpayer mid-level exception), but the Celtics are said to be more focused on avenues that would allow them to hold onto Hauser, who has proven himself as a valuable rotation piece and one of the NBA’s best shooters. The team agreed to acquire Simons and Georges Niang this week, but both players are candidates to be moved before they ever play a game for Boston.

The Celtics have already had an active offseason, but Stevens set the stage for more activity after the draft when he said he wants to retain Kornet and Horford. The team currently has minimal flexibility under the second apron and would need to cut even more salary to keep both big men while avoiding the tax. With Jayson Tatum “a long, long time” away from even having a projected timeline for his return from a ruptured Achilles, according to Stevens, the Celtics have more incentive to escape the tax now while he is still recovering from his injury. Resetting the harsh repeater tax, which they would do by avoiding the luxury tax for two consecutive seasons, would set them up with more of a runway to spend big in the future.

“Our owners, old and new, are committed to spending,” Stevens said Wednesday.

At the same time, Stevens acknowledged, “There’s a lot of things that go into these moves and a lot of things that are really important. And, listen, again, it goes back to prioritizing our flexibility.”

The Celtics knew they would eventually need to face cost-cutting decisions when they put together their 2024 championship roster. They are now dealing with the harsh reality of the NBA’s collective bargaining agreement. Vice president of basketball operations Mike Zarren said, “The fact of the matter is the new CBA is set up so that teams can’t spend enormous amounts of money for long periods of time.”

“There’s a bit of wistfulness always when guys move on,” Zarren said Thursday after the second round of the draft. “But at the same time, the rules are the same rules for everyone and we’ve got a lot of good players here and a lot of good assets here and we feel like we’ll be set up to compete really, really well in the near future. So that’s always heartening when you know that you’re in that spot. There’s a lot of teams that feel further from that than we do, I’m sure.”

Zarren said, “there’s a banner that will be here forever” because the Celtics were as aggressive as they were in the 2024 offseason.

“We sort of realized where we were a couple summers ago that we could take advantage of the situation with the assets we had and the salary situation we were in and the quality of players we already had,” Zarren said. “We could make a jump before the rules got as punitive as they were going to get. That was a very conscious decision at the time, and it worked.”

(Photo: Maddie Meyer/Getty Images)