The Boston Celtics, fresh off their strategic maneuvers in the Jrue Holiday trade, have once again captured the NBA spotlight with their latest move: acquiring Anfernee Simons. However, the ink on that deal has barely dried, and rumors are already swirling that the talented guard could be on the move again. According to The Athletic’s Jay King, the Celtics are exploring the possibility of flipping Simons’ $27.7 million expiring contract to align with their long-term goals of roster flexibility and retaining key free agents like Luke Kornet and Al Horford. With Jayson Tatum sidelined for most, if not all, of the 2025-26 season due to a torn Achilles, Boston’s front office, led by Brad Stevens, is making calculated moves to balance immediate competitiveness with future stability. This article dives into the implications of a potential Simons trade, his fit with the Celtics, and what it means for the franchise’s championship aspirations.
The Simons Acquisition: A Strategic Move in the Holiday Trade
The Celtics’ acquisition of Anfernee Simons came as part of the blockbuster Jrue Holiday trade, a deal that reshaped Boston’s roster while keeping them under the NBA’s second apron. Simons, a 26-year-old guard, brings a dynamic skill set to the table. Last season with the Portland Trail Blazers, he averaged 19.3 points and 4.8 assists per game across 70 games, shooting 36.3% from three-point range. His career 38.1% three-point shooting makes him a natural fit for Joe Mazzulla’s system, which emphasizes spacing and perimeter shooting. Simons’ ability to create his own shot and facilitate for others adds another dimension to a Celtics offense that will need to adapt without Tatum’s scoring prowess.
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
However, Simons’ $27.7 million expiring contract is a significant financial commitment for a team already navigating the NBA’s stringent salary cap rules. The Celtics’ decision to explore trading him, as reported by Jay King, reflects their broader strategy of maintaining roster flexibility. By moving Simons, Boston aims to create cap space and roster spots to retain free agents like Luke Kornet and Al Horford, both of whom have been integral to the team’s success. This approach underscores Brad Stevens’ reputation as a forward-thinking executive who prioritizes long-term sustainability without sacrificing competitiveness.
Why Trade Simons? Balancing Present and Future
The idea of flipping Simons so soon after acquiring him may seem surprising, but it aligns with Boston’s organizational priorities. As Jay King noted, the Celtics are focused on two key directives: regaining roster flexibility and securing a path to retain their free agents. With Tatum expected to miss most of the 2025-26 season, the Celtics are leaning on their core of Jaylen Brown, Derrick White, and a supporting cast that includes players like Kornet and Horford. Keeping this group intact while adding depth is critical, especially in a competitive Eastern Conference.
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
Simons, while talented, may not be a perfect long-term fit. His defensive limitations, combined with his hefty contract, make him an attractive trade chip for teams looking for a young, offensively gifted guard. An NBA personnel executive told Steve Bulpett of Heavy that “Boston’s still out there talking trade, and [Simons] could be gone if the right move comes along.” This suggests that the Celtics are open to deals that could bring in assets like draft picks, younger players, or contracts that better align with their financial goals. By moving Simons, Boston could acquire pieces that complement their core while avoiding the luxury tax penalties that come with being above the second apron.
Simons’ Fit in Boston: A Double-Edged Sword
On paper, Simons is an excellent fit for the Celtics’ system. His ability to shoot 38.1% from three over his career aligns perfectly with Mazzulla’s emphasis on spacing the floor. Simons’ playmaking (4.8 assists per game) and shot creation would provide a much-needed offensive spark in Tatum’s absence, allowing Brown and White to focus on their two-way roles. His youth and upside also make him a valuable piece for a team looking to remain competitive in the short term.
However, there are challenges. Simons’ defensive shortcomings could be exposed in Boston’s switch-heavy defensive scheme, especially against elite Eastern Conference guards like Donovan Mitchell or Tyrese Haliburton. Additionally, his expiring contract creates uncertainty. If the Celtics believe they can’t re-sign him at a reasonable price next offseason, trading him now for assets that fit their long-term vision makes sense. The fact that Boston has already navigated under the second apron by trading Holiday and Kristaps Porziņģis shows their willingness to make bold moves, and flipping Simons would be a continuation of that strategy.
The Bigger Picture: Building for Sustained Success
The Celtics’ exploration of a Simons trade is part of a broader plan to build a roster that can compete for championships beyond the 2025-26 season. With Tatum’s injury casting a shadow over the upcoming campaign, Stevens is focused on ensuring the team remains a contender when their star forward returns. Retaining players like Kornet, a versatile big man, and Horford, a veteran leader, is crucial for maintaining Boston’s defensive identity and locker room culture. By trading Simons’ contract, the Celtics could acquire players or picks that provide depth and flexibility, allowing them to navigate the cap constraints while building around Brown, White, and a healthy Tatum.
Moreover, the Celtics’ proactive approach in the trade market signals their confidence in their core. Jaylen Brown’s emergence as a Finals MVP and Derrick White’s two-way excellence provide a strong foundation, and adding complementary pieces through a Simons trade could elevate Boston’s ceiling. Whether it’s a defensive-minded wing, a cost-controlled role player, or future draft capital, the Celtics are positioning themselves to stay ahead of the curve in a rapidly evolving NBA landscape.
The Boston Celtics’ potential decision to trade Anfernee Simons is a testament to their strategic foresight and commitment to sustained success. While Simons’ offensive talents make him an intriguing fit, his expiring contract and defensive limitations make him a candidate for a trade that could unlock greater roster flexibility and secure key free agents like Luke Kornet and Al Horford. With Jayson Tatum sidelined, the Celtics are navigating a delicate balance between immediate competitiveness and long-term planning. Brad Stevens’ willingness to explore bold moves underscores Boston’s ambition to remain a championship contender, both now and in the future. As the trade rumors swirl, Celtics fans can take comfort in knowing their front office is playing chess, not checkers, in pursuit of another banner.