The Boston Celtics, fresh off a transformative offseason, are once again making waves in the NBA with their latest roster moves. After trading Jrue Holiday to acquire Anfernee Simons from the Portland Trail Blazers, the Celtics find themselves at a crossroads: keep the dynamic young guard to fill the scoring void left by Jayson Tatum’s absence or flip him to alleviate their looming luxury tax burden. With a new $5.5 million big man signing to replace Luke Kornet and Al Horford’s expected departure, Boston’s front office is navigating a delicate balance of financial prudence and championship ambition. Can Simons, a 27-year-old sharpshooter, become the key to their title hopes, or will he be rerouted in another blockbuster trade? Let’s break down the strategy, the stakes, and the potential impact of this pivotal decision.
The Celtics’ Salary Cap Conundrum
The Boston Celtics are no strangers to big moves, but their recent trade for Anfernee Simons in exchange for Jrue Holiday was driven by financial necessity as much as basketball strategy. Facing a massive luxury tax bill—potentially exceeding $100 million due to their star-studded roster—the Celtics needed to shed salary while maintaining competitiveness. Holiday, a defensive stalwart and playoff hero, was on a multi-year contract, while Simons, set to earn $27.7 million in the final year of his deal, offered a shorter-term financial commitment.
This trade was a calculated gamble to duck under the NBA’s punitive second apron, which imposes strict roster-building restrictions. However, Simons’ $27.7 million salary is still several million more than Holiday’s, making him a prime candidate for another trade. According to The Athletic’s Jay King, Boston is actively exploring options to reroute Simons before he even plays a game in green, potentially to a team like the Brooklyn Nets, who have cap space to absorb his expiring contract, or as part of a multi-team deal involving the Los Angeles Clippers. The Celtics’ goal is clear: maximize cap flexibility while building a roster capable of contending without Tatum.
Anfernee Simons: A Scoring Spark in Tatum’s Absence
With Jayson Tatum sidelined for the 2025/26 season due to an Achilles injury, the Celtics are in dire need of offensive firepower. Anfernee Simons, at just 27 years old, brings exactly that. Known for his silky three-point shooting and ability to create his own shot, Simons averaged 22.6 points, 5.5 assists, and 3.6 rebounds per game in the 2024/25 season with Portland. His explosive athleticism and knack for scoring in bunches make him a natural fit to fill Tatum’s role as a primary offensive creator alongside Jaylen Brown and Derrick White.
Simons’ youth and upside are significant. While not yet at the All-Star level, his development trajectory suggests he could blossom into a cornerstone player. His ability to stretch the floor (38.9% from three last season) and handle pick-and-roll situations would complement Boston’s fast-paced, spacing-heavy system under coach Joe Mazzulla. Keeping Simons could provide the Celtics with a long-term asset, especially if he thrives in a larger role. However, his expiring contract adds urgency to the decision: retain him and risk losing him for nothing in free agency, or trade him now for assets that address other roster needs.
The Case for Trading Simons
Despite Simons’ potential, the Celtics’ financial constraints make trading him an attractive option. As CBS Sports’ Brad Botkin predicts, Boston is likely to flip Simons to avoid the luxury tax’s harsh penalties. The Nets, with their ample cap space, could absorb Simons’ $27.7 million salary in exchange for a draft pick or a young player, while the Clippers have been mentioned as a potential destination in a more complex deal. Such a trade could net the Celtics a starting center—a critical need with Al Horford expected to leave and Luke Kornet already gone in free agency.
The Celtics’ recent $5.5 million signing of a new big man to replace Kornet is a step toward addressing their frontcourt depth, but it’s not enough for a championship contender. A trade involving Simons could bring back a proven center, such as a player like Clint Capela or Nikola Vucevic, who could anchor the paint and complement Boston’s perimeter-heavy roster. This move would also allow the Celtics to stay under the luxury tax threshold, preserving flexibility for future signings or trades. However, trading Simons risks depleting Boston’s scoring depth, especially without Tatum, making the return package critical to the deal’s success.
The Broader Roster Shake-Up
The Simons trade is just one piece of a larger offseason overhaul for the Celtics. In addition to trading Holiday, Boston dealt Kristaps Porzingis, a key contributor to their 2024 championship, and let Kornet walk in free agency. These moves reflect a strategic pivot toward a younger, more cost-effective roster while maintaining a competitive edge. With Jaylen Brown stepping into the primary leadership role and Derrick White providing defensive stability, the Celtics are betting on their core to carry them through a transitional season.
The Eastern Conference, weakened by injuries to stars like Tatum, Tyrese Haliburton, and Damian Lillard, presents an opportunity for Boston to remain contenders. However, the loss of Horford and the uncertainty at center could expose vulnerabilities against physical teams like the Philadelphia 76ers or Milwaukee Bucks. Trading Simons for a rim-protecting big man could address this weakness, but it would require precise execution from president of basketball operations Brad Stevens, who has a reputation for bold yet calculated moves.
Challenges and Risks
The decision to keep or trade Simons is fraught with risks. If the Celtics retain him, they face the challenge of integrating a ball-dominant guard into a system built around Brown and White, potentially disrupting chemistry. Additionally, Simons’ expiring contract means Boston could lose him for nothing if he doesn’t re-sign in 2026. On the other hand, trading Simons could backfire if the return package doesn’t adequately address the team’s needs or if the new center fails to gel with the roster. The absence of Tatum already puts pressure on Boston’s offense, and losing Simons’ scoring could make it harder to compete in a wide-open East.
Moreover, Simons’ defensive limitations are a concern. While he’s improved as a defender, he’s not on the same level as Holiday, whose elite perimeter defense was a cornerstone of Boston’s success. Any trade involving Simons must account for this gap, ensuring the Celtics don’t sacrifice too much defensive versatility. The front office’s ability to navigate these challenges will determine whether this offseason is remembered as a masterstroke or a misstep.
The Boston Celtics’ decision on Anfernee Simons is a pivotal moment in their 2025/26 season. Keeping the 27-year-old guard could provide the offensive spark needed to stay competitive without Jayson Tatum, while trading him could unlock the cap space and assets to address critical roster gaps, particularly at center. As the luxury tax looms and the Eastern Conference opens up, Boston’s front office faces a high-stakes choice that could define their championship hopes. Will Simons don the green and become a fan favorite, or will he be the key to landing a game-changing big man? Celtics Nation is buzzing with anticipation, and the NBA world is watching closely to see how this saga unfolds.