Just two months after acquiring Anfernee Simons from the Portland Trail Blazers, the Boston Celtics find themselves grappling with the same dilemma that plagued Portland: a talented offensive player whose trade value doesn’t match his on-court production. Simons, a 26-year-old combo guard, is a scoring dynamo, averaging around 20 points per game over the past three seasons while shooting an impressive 38.1 percent from beyond the arc. His ability to stretch the floor and provide secondary playmaking makes him a natural fit for Joe Mazzulla’s three-point-heavy Celtics offense, which led the NBA in three-point attempts last season. Yet, for all his offensive brilliance, Simons’ defensive shortcomings and expiring contract create a puzzle that Boston is struggling to solve.
Simons’ game is tailor-made for the modern NBA. His quick release and deep range make him one of the league’s premier shooters, capable of igniting scoring runs and creating space for teammates. For a Celtics team that thrives on spacing and ball movement, Simons could seamlessly slot into their system—potentially as a high-impact sixth man, allowing rising star Payton Pritchard, fresh off a Sixth Man of the Year campaign, to step into the starting lineup. This move could keep Boston’s offense humming, even as they navigate a transitional season without superstar Jayson Tatum, who continues to recover from a devastating Achilles tear.
But there’s a catch. Simons’ defensive deficiencies are glaring. Over his seven seasons in Portland, he consistently ranked near the bottom of the Blazers’ roster in defensive rating. His slight frame and lack of lateral quickness make him a target for opposing offenses, a liability that could haunt a Celtics team already retooling after trading away defensive stalwarts Jrue Holiday and Kristaps Porzingis to manage their salary cap. While Simons’ scoring prowess is undeniable, his one-dimensional play limits his overall impact, especially for a team with championship aspirations.
Boston’s front office, led by Brad Stevens, has masterfully navigated the salary cap in recent years, positioning the team for long-term success around core players like Tatum, Jaylen Brown, Derrick White, and the ascending Pritchard. However, Simons’ $27.7 million expiring contract presents a challenge. As a prolific scorer entering his prime, he could command a similar—or even higher—salary in his next deal. Committing significant cap space to a player whose defensive limitations cap his ceiling could jeopardize Boston’s flexibility, especially as they aim to rebuild a roster capable of contending once Tatum returns.
The Celtics are now in the same bind Portland faced. The Blazers recognized that Simons, while talented, didn’t align with their rebuilding timeline. His expiring contract made him a risky long-term investment, and his trade value suffered as teams hesitated to take on a player who could walk in free agency. Portland ultimately traded Simons to Boston, salvaging what value they could. Now, the Celtics are struggling to find a market for him, with teams around the league wary of his contract status and defensive shortcomings.
Portland’s experience with Simons offers a cautionary tale. The Blazers held onto him too long, watching his trade value erode as his contract neared its end. They faced a similar issue with players like Jerami Grant and even Jrue Holiday, whose contracts and skill sets didn’t align with the team’s long-term vision. By moving Simons when they did, Portland avoided being locked into a costly deal for a player who, while gifted, couldn’t elevate their ceiling. Boston, however, risks repeating Portland’s mistake if they hesitate to act.
The Celtics could keep Simons as a sixth man, leveraging his scoring to bridge the gap during Tatum’s recovery. But this is a short-term fix for a team with bigger ambitions. Paying a premium for a player whose defensive struggles limit his role in a championship-caliber lineup doesn’t make sense, especially when Stevens has other options to retool the roster. The longer Boston waits, the more Simons’ trade value could dwindle, leaving them with little return on a player who doesn’t fit their long-term vision.
Boston’s championship window remains open, thanks to their core of Brown, White, and Pritchard, with Tatum’s eventual return looming as a game-changer. But to maximize that window, the Celtics need to avoid the trap Portland fell into with Simons. His offensive gifts are tantalizing, but his defensive limitations and looming free agency make him a risky bet. Stevens, known for his shrewd roster moves, must find a way to flip Simons for assets that better align with Boston’s goals—whether that’s a defensive-minded wing, a versatile big, or draft capital to fuel future trades.
The Blazers learned the hard truth about Anfernee Simons: talent alone isn’t enough if it doesn’t fit the bigger picture. Now, it’s Boston’s turn to face that reality. The clock is ticking, and the Celtics can’t afford to let Simons’ value slip further. For a franchise built on making tough decisions, this is one that could define their path back to contention.