It's not an either-or situation with Anfernee Simons and luxury tax threshold
That said, it is not an either-or situation with Simons and the luxury tax threshold. If Stevens and the Celtics choose to completely punt this 2025-26 campaign in order to reset all the restrictions that come with the luxury tax and it's aprons, it is not mandatory that his $27,678,571 salary for this season is offloaded this summer.
Stevens, Joe Mazzulla, and company could see how he fits in training camp and preseason. See if he has the tools to become an adequate defender, have success playing off the ball, etc. They could still trade him after a quarter of the season and $20 million of his salary would be off the books. Or halfway through the season and just shy of $14 million would be reduced from the Celtics' payroll.
While the benefit of trying to trade him prior to the season is more teams should be open to making a move now and you could potentially dump more money off your books, you also miss out on seeing how he could fit in Boston. He could potentially excell and you get a better package come the trade deadline. Or he could mesh great with Derrick White and Payton Pritchard and he agrees to an extension next summer which works for the team financially.Notice how the Celtics haven’t had a press conference to introduce Anfernee Simons? That’s because he’s getting traded again. https://t.co/m7mRHjvDLp
— CelticsLife.com (@celticslife) July 23, 2025
The point is it's not about $27.7 million or $0. There's a lot in between. And to be quite honest if there had been a team willing to absorb Simons' $27.7 million without sending the Celtics anything back, Stevens would have flipped him already. Even if Simons is traded this summer, it won't be a savings of $27.7 million it will be that number minus the contract or contracts that are coming back in return.
Considering the return for Porzingis was also just one player in Georges Niang who if Stevens had his druthers would have been flipped elsewhere for nothing for the savings, it's rather imperative that the Celtics get back to finding value. Whether through acquiring draft picks who pan out or otherwise.
An improved Simons would add value whether for the team or in a future trade. Taking a shot on Anfernee could prove dividends and again you could always get off most of the money 20 games into the season.