In a stunning turn of events, the Boston Celtics, fresh off their blockbuster trade sending Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons, are already plotting their next move. According to a recent report from The Athletic‘s Jay King, the Celtics are actively exploring options to flip Simons’ $27.7 million expiring contract, signaling that the young guard’s time in Boston may be short-lived.
The move aligns with Boston’s broader strategy, as outlined by President of Basketball Operations Brad Stevens following the first round of the 2025 NBA Draft. Stevens emphasized two key priorities: restoring roster flexibility and securing a path to retain key free agents like Luke Kornet and Al Horford. Trading Simons, who was acquired as a centerpiece in the Holiday deal, could help the Celtics achieve both goals while reshaping their roster for the future.
Adding fuel to the fire, an NBA personnel executive told Heavy‘s Steve Bulpett that “Boston’s still out there talking trade, and [Simons] could be gone if the right move comes along.” This suggests the Celtics are not fully committed to integrating the 26-year-old guard into their long-term plans, despite his impressive skill set.
Even after the changes, Brad Stevens said the Celtics have a foundation with Jayson Tatum, Jaylen Brown, Derrick White, Payton Pritchard and others that a lot of teams would love to have.
— Jay King (@ByJayKing) June 26, 2025
On paper, Simons seems like a perfect fit for Boston’s high-octane, three-point-heavy system under head coach Joe Mazzulla. Last season with the Trail Blazers, he averaged 19.3 points and 4.8 assists over 70 games, shooting a respectable 36.3% from beyond the arc. His career three-point shooting clip of 38.1% makes him a natural complement to Boston’s spacing-oriented offense. However, with Jayson Tatum sidelined for most, if not all, of the 2025-26 season due to a torn Achilles, the Celtics appear to be prioritizing long-term flexibility over immediate contributions from Simons.
Brad Stevens stressed he would like to bring back Al Horford and Luke Kornet. He called that a Celtics priority.
Also said they will prioritize flexibility. Could that mean the Celtics keep making salary cuts to get under the luxury tax? I would guess they try to do that, if…
— Jay King (@ByJayKing) June 26, 2025
Boston’s front office has already made waves this offseason, maneuvering under the NBA’s second apron by trading both Holiday and Kristaps Porziņģis. These moves have given the Celtics some financial breathing room, but they’re not done yet. With the core of Jaylen Brown, Derrick White, and the injured Tatum expected to remain intact, flipping Simons could be the next step in building a sustainable contender for future seasons.
As the rumor mill churns, one thing is clear: the Celtics are playing chess, not checkers. Trading Simons so soon after acquiring him would be a bold statement, proving that no player is untouchable as Boston chases another championship. Fans will be watching closely to see if the “right move” materializes—and whether Simons’ brief stint in green comes to an abrupt end.