Celtics Weighing Trade of Anfernee Simons in Latest Cost-Cutting Move
The Boston Celtics‘ busy offseason may still have another major twist. After already dealing away Jrue Holiday and Kristaps Porzingis to shed salary and retool their roster, the Celtics are now reportedly considering moving newly acquired guard Anfernee Simons in another attempt to trim costs.
Simons came to Boston as part of the Jrue Holiday trade with the Portland Trail Blazers. Despite his proven scoring ability and offensive talent, sources told The Athletic’s Jay King that Boston is weighing the possibility of flipping Simons and his $27.7 million expiring contract to free up cap space.
President of Basketball Operations Brad Stevens is focused on staying under the luxury tax threshold and re-signing key veterans like Luke Kornet and Al Horford. Even after the Holiday and Porzingis trades, Boston remains about $15 million above the tax line, and moving Simons could be the most efficient way to balance the books.
Simons averaged 19.3 points and 4.8 assists last season while shooting 36.3% from deep. But his ideal role—ball-dominant and score-first—may not mesh with head coach Joe Mazzulla’s system. With Derrick White entrenched as the starting point guard and Jaylen Brown expected to handle more playmaking while Jayson Tatum recovers from a torn Achilles, Simons could struggle to carve out a defined role.
Additionally, his defensive shortcomings clash with Boston’s identity as a defense-first team. But the real value in Simons may lie in his contract, which could be Boston’s final major trade asset in its quest to avoid the repeater tax. Escaping the tax for two straight seasons would reset Boston’s repeater status, giving the team more cap flexibility down the line—crucial for managing Tatum’s looming supermax deal and keeping the core together.
Stevens has emphasized the importance of keeping Kornet and Horford, calling them vital to the franchise after the draft. While Sam Hauser has been mentioned in trade talks, Boston reportedly prefers to retain the sharpshooter because of his affordability and floor-spacing ability.
In what’s become a dramatic summer for the reigning NBA champions, the Celtics’ front office is clearly thinking long-term. Tatum’s injury offers a temporary opportunity to restructure financially, and Simons’ contract could be the linchpin in that plan—even if he never ends up playing a game for Boston.
Ultimately, parting with Simons might not be about what he brings on the court, but what he allows the Celtics to do off it: preserve their roster, protect their financial flexibility, and build toward another title run when their superstar returns.