The Boston Celtics have been making waves this offseason, orchestrating a series of bold moves to reshape their roster while navigating the NBA’s complex financial landscape. With the goal of slipping under the second apron of the luxury tax—a target set firmly by President of Basketball Operations Brad Stevens—the Celtics have already traded away two starters. However, with the team still roughly $20 million over the second apron, the front office is far from done.
At the heart of Boston’s maneuvering is Anfernee Simons, the sharpshooting guard acquired in the blockbuster trade that sent Jrue Holiday elsewhere. Simons, with his expiring contract and elite 3-point shooting, is a tantalizing asset for a Celtics squad that led the NBA in 3-point attempts last season. Yet, the team is actively exploring trade options to offload his salary, a move that could prove pivotal in achieving their financial objectives without compromising their championship aspirations.
According to Heavy Sports, the Celtics are playing the long game, refusing to rush into a deal for Simons unless the return is right. “You never know, but the team they have now is probably the team they’ll start the year with,” a general manager told the outlet. “They could get themselves involved in some blockbuster. But they’re not in a hurry to make that move (on Simons).” This calculated approach underscores Boston’s confidence in their current roster while keeping the door open for a game-changing trade.
Simons is no ordinary trade chip. Last season with the Portland Trail Blazers, the 26-year-old averaged an impressive 19.3 points, 2.7 rebounds, and 4.8 assists per game, shooting 42.6% from the field and 36.3% from beyond the arc. His ability to catch fire from deep and score efficiently without dominating the ball makes him an ideal fit for Boston’s high-octane, 3-point-heavy offense. Whether he’s launching from downtown or creating off the dribble, Simons brings a dynamic scoring punch that could keep the Celtics firmly in the title conversation for the 2026-27 season—if he stays.
Still, Stevens and the Celtics’ front office are laser-focused on financial flexibility. Simons’ expiring deal, while valuable, represents a significant salary cap hit. If Boston can’t find a suitable trade partner, they may need to part ways with other players to achieve their goal of ducking under the second apron. The stakes are high: getting under the second apron would give the Celtics more room to maneuver in future free agency periods and avoid punitive luxury tax penalties.
As the offseason unfolds, all eyes are on Boston’s next move. Will they hold onto Simons, leveraging his scoring prowess to maintain their status as Eastern Conference juggernauts? Or will Stevens pull off another masterstroke, flipping Simons in a deal that reshapes the franchise and keeps their championship window wide open? With just weeks to go before critical decisions are made, the Celtics’ front office is proving once again why they’re among the NBA’s savviest operators.