The Portland Trail Blazers officially sent Anfernee Simons to the Boston Celtics just last month, but there's already a possibility that Boston isn't Simons' final destination. NBA insider Marc Stein reports that the Celtics have been exploring trade options for Simons [subscription required].
"League sources say Boston continues to explore its trade options with newly acquired Anfernee Simons, who became a Celtic as part of the trade that sent Jrue Holiday to Portland," Stein wrote.
Trail Blazers continue to bail out the Celtics
The Celtics made their offseason intentions clear from the start: they wanted to shed salary. Jayson Tatum's brutal Achilles injury may have been a factor in that decision. However, according to Brad Stevens, it was primarily the second apron that led to players like Holiday and Kristaps Porzingis being moved.
"The second apron is why those trades happened. I think that those were pretty obvious. And the basketball penalties associated with those are real," Stevens said.
Portland helped Boston win their championship in 2024 by trading them Holiday, who turned out to be their final Infinity Stone. This summer, the Blazers helped the Celtics achieve their goals yet again, confusingly taking Holiday and his three-year, $104 million contract back after he's shown concerning signs of declining play.
Celtics must come to same Anfernee Simons realization Blazers made
Boston now has Simons' expiring $27.7 million deal, giving them relatively more flexibility. Regardless of who Simons is as a player, that contract alone makes this a win for Boston. They could've traded for anyone with that salary and still won the deal given their cap situation, Tatum's injury, and Holiday arguably being a negative asset. The fact that they landed Simons -- one of the league's best shooters and a solid secondary playmaker just entering his prime -- makes this another Brad Stevens masterclass at Portland's expense.
But now, Boston faces the same dilemma as Portland had with Simons. Yes, he's a great player, but does he impact winning enough to justify his next contract?
Portland's situation was slightly different as they needed to clear room for Scoot Henderson and Shaedon Sharpe to grow. Simons is also a better fit in Boston because of "Mazulla ball," the style of basketball that head coach Joe Mazzulla prefers his team to play. Boston led the league in three-point attempts (48.2 per game) by a wide margin, which would bring out the best in Simons, a career 38.1 percent three-point shooter.
That said, Boston is one of the smartest front offices in the league. This summer, they escaped a potentially disastrous situation surprisingly easily (thanks to Portland and Atlanta). Boston's core of Tatum, Jaylen Brown, Derrick White, and Payton Pritchard are all locked up for multiple years. Still, Stevens understands how selective he needs to be in handing out deals under the new CBA. Committing long-term to Simons essentially means committing to that being their core going forward. That's not a high enough ceiling for another championship.
Like Portland did, Boston must trade Simons and make the ceiling limitations that come with his looming contract some other team's problem.