With Jayson Tatum’s injury making a championship run for the Boston Celtics unlikely this season, Boston’s goal this summer has been clear: get under the salary cap’s second apron. A team over the second apron is subject to severe restrictions, including a ban on trading first round picks, loss of the ability to use salary exceptions, and significant limitations on how trades can be constructed. Every roster decision this off-season made by Boston should be viewed through the lens of avoiding the second apron,
and this includes the trade they made sending Jrue Holiday to the Portland Trail Blazers for guard Anfernee Simons.
Steve Bulpett of Heavy.com dives into the Simons situation from the Boston perspective. Heavy.com quotes an anonymous NBA GM as saying, “They’re still very much willing to talk about Simons.” If the Celtics could somehow move Simons for assets without taking on more salary and/or long salary obligations it’s hard to imagine that Boston wouldn’t pursue the opportunity. In some NBA circles, another Simons trade is assumed to be inevitable.
Blazers fans might have a different perspective. As intriguing as Jrue Holiday is for the Blazers, it’s hard to imagine that Portland wouldn’t have been even more interested in a deal for Simons that would have brought back assets without also being saddled with a potentially onerous longer-term contract. With the Blazers apparently unable to find such a deal and no trade yet by Boston to move out Simons, it doesn’t appear that anyone is offering that kind of deal. Boston is in no position to take back more salary obligations like the Blazers were able to do, even if the Celtics could turn Simons into a more talented player. The NBA can be full of surprises, but we’ve now seen a lot of evidence to suggest that favorable deal for Simons that doesn’t return lots of salary simply isn’t out there.
Let’s assume for the moment that Simons is staying in Boston for the year. With Jayson Tatum out for the foreseeable future after suffering a torn left Achilles tendon in last season’s playoffs, it’s an open question where Boston’s scoring will come from. Jaylen Brown can put points on the board when he’s healthy, but he is coming off of knee surgery. After that, proven scoring is harder to come by. Enter Simons. He can definitely score, something Blazers fans are well aware of. Perhaps those that are casting Simons as surplus to requirements in Boston aren’t looking at things the right way.
An anonymous NBA personnel executive is quoted by Bulpett with this perspective:
“I bet you he’s their leading scorer,” he said. “Even with Jaylen. He’s going to have the ball a lot, and that dude can really score. That offense is going to have to change to accommodate him, and, on the last year of his contract, he’s going to let it fly.
“As the kids say, he’s a bucket. He is. That dude is a bucket. He can really fill it up. And remember, he was averaging around 20 in the West. What do you think he’s going to do in the Eastern Conference, which is a LOT less competitive? How’s he not going to score and score big?”
So what happens if Simons starts the season with Boston and plays really well? Regardless of how the Celtics really feel about Simons, his contract expires at the end of the 2025-26 season. It’s hard to imagine the Celtics offering him a new deal, even if he does play really well. The CBA makes really makes it difficult to pay what’s owed to Tatum, Brown, and Derrick White while still offering Simons a healthy contract. Unless he far exceeds all possible expectations, Simons is probably more valuable to the Celtics simply as an expiring contract rather than a player to commit long-term salary to.
While many Blazers fans had expected a deadline trade moving Simons out last spring that never materialized. Presumably Boston will find it easier to move him at the deadline with only months remaining on the contract. If Simons isn’t traded though, Boston will almost certainly just let his contract run out. It may be unfortunate if it plays out that way for both Boston and Simons, but the CBA can be especially cruel for this particular situation.
For now, all Simons can do is play his best basketball, keep his bags packed, and see how things shake out. The Celtics will surely continue to take this season with Tatum’s injury as an opportunity to see what they can do to make their salary situation as manageable as possible. Where Simons will be playing 2026 is anybody’s guess.
