Just weeks after shocking fans with the decision to part ways with Jrue Holiday—one of the cornerstones of their 2024 NBA championship run—the Boston Celtics are once again at the center of attention with a new report: they are still actively trying to trade Anfernee Simons, a player acquired in early July 2025 via a deal with the Portland Trail Blazers.
According to reliable NBA insiders such as Michael Pina (The Ringer) and Jake Fischer (Yahoo Sports), the Celtics are “scanning the league” for potential trade partners willing to take on Simons—a young offensive talent who, while skilled, may not be an ideal fit for Boston’s current roster structure or playing philosophy.
Why do the Celtics want to “flip” Simons?
From a basketball standpoint, Anfernee Simons is far from a bad player. At 26, he possesses great speed, strong ball-handling skills, and a dangerous three-point shot. However, the Celtics—built on a foundation of rock-solid defense, versatility, and disciplined team play—don’t necessarily need another isolation scorer like Simons at this point.
Adding to the issue, Simons carries a salary of approximately $24 million per year under a 3-year, nearly $75 million contract. That’s a considerable financial burden, especially as the Celtics try to avoid crossing the dreaded “second tax apron” and facing other strict penalties under the NBA’s new financial rules.
As a result, team management—particularly President of Basketball Operations Brad Stevens—is looking for a viable exit strategy for Simons, either by trading him for a cheaper player or converting his value into future assets such as draft picks.
Obstacle: Can’t trade until after September 7
The biggest hurdle is timing. Under NBA regulations, players acquired via trade in July—like Simons and Georges Niang—cannot be traded again until after September 7, 2025. This means that the Celtics are effectively locked out of any trade involving Simons for the next two months, despite their clear intentions.
Experts believe that once that date passes, Boston will immediately trigger further roster restructuring moves, and Anfernee Simons is expected to be one of the first names back on the trading block.
Confused fans: What’s the real direction?
Letting go of Jrue Holiday—a major contributor to their 2024 title—only to then try and move Simons (the player acquired in Holiday’s place) has raised serious questions about the Celtics’ long-term strategy. Are they truly focused on defending their crown and building a dynasty, or are they just navigating a financial puzzle?
In the meantime, Sam Hauser—one of the team’s beloved young players who just signed a $45 million deal—is also rumored to be “the next one out.” Many fans are beginning to worry that Boston may be sacrificing roster stability and risking a domino effect of internal disruption.
In conclusion
The Boston Celtics are heading into the 2025–2026 season with more questions than answers. All eyes are now on the front office at TD Garden, where Brad Stevens and his team must make critical decisions—not only to stay competitive on the court but to maintain the trust and faith of their loyal fan base.
Anfernee Simons may just be the first step in a much larger transformation—one that could shape the entire future of the reigning NBA champions.
