Boston Celtics president of basketball operations Brad Stevens has not had a single easy decision to make personnel-wise since Jayson Tatum tore his Achilles tendon during the 2025 NBA Playoffs. That will continue to be the case throughout the 2025-26 season, barring any potential moves ahead of the trade deadline.
With the Celtics still not clear of the CBA's first tax apron, Stevens has one more difficult decision to make. On Tuesday, a report from The Athletic's Jay King made it clearer what choice Stevens would pursue: Trading away Anfernee Simons and clearing his gaudy $27.7 million salary off the books.
"If the Celtics can get out of the luxury tax entirely — and begin the process of resetting the repeater tax — they should do it," King wrote. "Even if they can’t find a (Anfernee) Simons trade (or a series of trades) that would shed that much money, it would be smart to move him in another salary-cutting trade if they don’t consider him a part of the long-term future."
Assuming King is right, it's clear that the upcoming season will be Simons' first and last in Beantown.
Anfernee Simons Won't Stay with Celtics for Long
Simons was the odd man out in Boston the day he was acquired by Stevens for Jrue Holiday and two second-round picks from the Portland Trail Blazers. While he could do damage offensively in head coach Joe Mazzulla's up-tempo offense, his defensive prowess, or lack thereof, makes for a questionable culture fit.
Especially when you consider that he was one of the few bright spots for a downtrodden Portland Trail Blazers team that hasn't made the postseason since the 2020-21 season, but only on one side of the ball. His team was always good enough to shine, but never good enough with Simons as the No. 1 option. That sounds like a one-way trip to an NBA Play-In seed, the opposite of what Stevens wants.
Simons would've had a better chance of sticking had the franchise been confident enough to make a playoff run without Tatum and with Jaylen Brown leading the charge. Stevens seems hellbent on leaving the cupboard bare for the 2026-27 season, when Tatum will be back to full health for the entire campaign.
It'll be interesting to see how Stevens will view the Celtics' outlook if the losses quickly pile up. But if there are too many wins early on and the temptation to improve via trade is there, Simons's time in Boston could end sooner rather than later.