The Boston Celtics have been making waves this summer, reshaping their roster with blockbuster trades that sent Kristaps Porziņģis to the Atlanta Hawks and Jrue Holiday to the Portland Trail Blazers, all to stay under the NBA’s second apron. But the drama doesn’t end there—NBA insider Jake Fischer reports that Anfernee Simons, acquired in the Holiday deal, could be on the move again before the February 5, 2026, trade deadline. With Jayson Tatum sidelined for the 2025-26 season due to a torn Achilles, the Celtics appear to be embracing a bridge year, leaning on Jaylen Brown and Derrick White to keep them competitive. Simons, a dynamic 26-year-old guard, brings scoring punch but is on an expiring $27.6 million contract, raising questions about his fit and future. Can Boston maximize Simons’ value, or is he just a one-year rental? Let’s dive into this high-stakes offseason and what it means for the Celtics in a post that’s sure to spark debate among fans!
I estimate the Celtics have now reduced roster expenses by $286 million since the start of the offseason by trading:
-Jrue Holiday for Anfernee Simons
-Kristaps Porinzgis for Georges Niang
-Niang for nothingThey’d clear another $40 million by getting under the tax.
— Yossi Gozlan (@YossiGozlan) August 5, 2025
The Celtics’ summer moves signal a strategic pivot, balancing financial constraints with playoff aspirations in a Tatum-less season. Simons’ potential trade looms large, with implications for Boston’s short-term competitiveness and long-term roster-building. Below, we analyze Simons’ role, the Celtics’ bridge-year strategy, and the trade scenarios shaping their future.
Anfernee Simons: A Temporary Spark or Trade Bait?
Acquired from Portland in the Jrue Holiday trade, Anfernee Simons brings a much-needed scoring boost to Boston’s backcourt. Last season, the 26-year-old averaged 19.3 points and 4.8 assists, shooting 42.6% from the field and 36.3% from three. His ability to create his own shot and stretch defenses makes him a valuable asset alongside Jaylen Brown and Derrick White, especially with Tatum out. However, Simons is on an expiring $27.6 million contract, set to hit free agency in 2026. Jake Fischer notes that “the expectation persists” that Boston will explore trade talks for Simons through the trade deadline, suggesting he’s more of a placeholder than a long-term piece. At 6-foot-3, with quick handles and a smooth jumper, Simons could thrive in Brad Stevens’ system, but his next contract—projected at $20-25 million annually—may not fit Boston’s cap situation, making a trade likely.
A Bridge Year Without Tatum: Brown and White Take the Lead
Jayson Tatum’s torn Achilles, suffered in a February 2025 game, is a devastating blow to Boston’s championship hopes. The 27-year-old All-NBA star, who averaged 30.1 points and 8.8 rebounds last season, is expected to miss the entire 2025-26 campaign. Without him, the Celtics pivot to a bridge year, leaning on Jaylen Brown (2024 Finals MVP, 27.0 PPG) and Derrick White (elite two-way guard, 15.2 PPG, 5.2 APG) to keep them in the playoff hunt. The duo, combined with role players like Al Horford and Payton Pritchard, gives Boston a shot at a low seed in the East, but few see them as true contenders against juggernauts like Milwaukee or Philadelphia. Simons’ scoring could bridge the gap, but his expiring deal and the team’s $145.7 million commitment to Tatum, Brown, and White make long-term retention unlikely. Boston’s front office must decide whether to ride with Simons or flip him for assets that better align with their future.
Financial Strategy: Navigating the Second Apron
The trades of Porziņģis and Holiday were driven by the NBA’s punitive second apron, which imposes harsh penalties on high-spending teams. By moving Porziņģis ($29.7 million) and Holiday ($30.1 million), Boston freed up cap space while acquiring Simons and other assets. However, with Tatum ($34.8 million), Brown ($57.0 million), and White ($53.9 million) eating up $145.7 million in 2025-26, re-signing Simons at his projected $20-25 million per year could push the Celtics back into luxury tax hell. Instead, GM Brad Stevens is prioritizing cost-controlled role players or a potential star acquisition to complement Tatum’s return in 2026-27. Trading Simons before or at the deadline could yield draft picks, young talent, or a player on a team-friendly deal, aligning with Stevens’ track record of savvy roster management.
Trade Scenarios: Maximizing Simons’ Value
Boston’s approach to Simons is flexible, with multiple paths forward. They could keep him for the season, leveraging his 19.3 PPG to boost their playoff chances, then explore a sign-and-trade in 2026 to avoid losing him for nothing. Alternatively, trading him before the February 5 deadline could net immediate help—perhaps a defensive wing or a versatile big to bolster the rotation. Fischer’s report suggests Boston is open to deals now, but they could also carry Simons into the season to assess their playoff ceiling. If Brown and White keep Boston competitive (say, a top-six seed), Stevens might hold off on a trade, banking on Simons’ scoring to steal a playoff series. If the season falters, Simons becomes a prime trade chip for teams needing a young, dynamic guard. Either way, his one-year rental status makes him a short-term solution with long-term trade potential.
The Bigger Picture: A Season of Transition
The Celtics’ 2025-26 season is about survival and strategic positioning. Without Tatum, their ceiling is limited, but Brown and White ensure they’re not lottery-bound. Simons’ addition provides offensive firepower, but his expiring contract and Boston’s cap constraints make him a likely trade candidate. The Porziņģis and Holiday deals reflect a broader plan to reset financially while staying competitive, setting the stage for a reloaded roster when Tatum returns. Stevens’ willingness to explore trades for Simons shows a franchise unwilling to stand pat, even in a bridge year. The challenge is balancing immediate needs—staying afloat in a tough East—with long-term goals, like pairing Tatum with another star or deepening the bench. For fans, this season promises intrigue: can Simons prove his worth, or will Boston cash in on his value?
The Boston Celtics’ offseason has been a whirlwind, with Anfernee Simons’ potential trade adding fuel to the fire. His scoring punch offers hope in a Tatum-less season, but his expiring contract and Boston’s cap crunch make him a likely one-year rental. Jaylen Brown and Derrick White will keep the Celtics competitive, but the front office’s focus on cost-controlled assets and future flexibility signals a bridge year with bigger plans for 2026-27. Whether Boston keeps Simons or trades him by February, this move will shape their path forward.