Celtics May Flip Anfernee Simons To Free Up Room For Two Key Stars

The Boston Celtics’ whirlwind offseason may not be finished just yet. After trading away Jrue Holiday and Kristaps Porzingis to clear salary and reshape the roster, Boston is reportedly exploring yet another cost-cutting move, this time centered on newly acquired guard Anfernee Simons.

Simons arrived in Boston as part of the Holiday trade with Portland. But despite his undeniable scoring ability and smooth offensive game, league sources told The Athletic’s Jay King that the Celtics are considering flipping Simons and his $27.7 million expiring contract. The motive is clear: financial flexibility. 

President of Basketball Operations Brad Stevens wants to re-sign key veterans Luke Kornet and Al Horford while positioning the team below the luxury tax threshold. That’s a tall order, even after the Holiday and Porzingis deals, and Simons’ sizable expiring deal is an obvious lever to pull.

While Simons averaged 19.3 points and 4.8 assists on 36.3 percent shooting from three last season, his long-term fit in Boston’s system under Joe Mazzulla was already in question. 

He’s best with the ball in his hands, and with Derrick White entrenched as the starting point guard and Jaylen Brown expected to take on even more creation duties while Jayson Tatum recovers from a torn Achilles, Simons could find himself the odd man out. 

He has value as a score-first guard with deep shooting range, but his defensive limitations and need for usage make him a tough fit in Boston’s defense-first identity.

More importantly, his expiring contract is one of the last big trade chips the Celtics hold. Stevens is laser-focused on avoiding the repeater tax, which penalizes teams that exceed the luxury tax in consecutive years. 

Boston currently sits roughly $15 million over the tax line, and trimming that would not only allow them to avoid the financial penalties but also hit the NBA’s “reset” button. 

Escaping the tax for two straight years wipes the repeater status, granting teams more flexibility in future seasons. That flexibility could prove crucial once Tatum returns and Boston decides how to maneuver around his upcoming supermax deal and maintain its core.

Veterans like Kornet and Horford are also part of the equation. Stevens called them “huge parts of this organization” after the draft, making it clear that keeping them is a priority. 

But to do so while staying under the tax, moving Simons might be the only way. Sam Hauser’s name has surfaced as another possible trade chip, but the Celtics reportedly prefer to keep him due to his elite shooting and low cap hit.

Boston already shocked the league by unloading two of their starters just a year after winning a title. But the front office is embracing a long-term view. Tatum’s injury gives them a window to regroup financially, and Simons’ $27.7 million could be the key to unlocking it, just after saving $260 million in two trades. 

While he may never suit up in green, Simons could end up playing a major role in helping Boston retain its core and preserve its flexibility for a more competitive return in 2026.