Boston Grapples with Anfernee Simons Conundrum as NBA Trade Deadline Looms

Anfernee Simons delivered a commanding performance for the Boston Celtics on Thursday, January 25, 2024, scoring 39 points in their 119-114 victory over the Miami Heat. This career-high offensive explosion with the franchise, achieved entirely off the bench, established a new Celtics record for scoring by a reserve in a road game. Simons’ late-game heroics, including two crucial free throws in the closing seconds, not only sealed a critical win but also reignited discussions about his future as the NBA trade deadline on February 5 approaches.

Simons, who arrived in Boston as part of the multifaceted offseason trade that brought Jrue Holiday to the Celtics, has been a consistent subject of trade speculation since donning the green and white. His recent scoring surge against the Heat, particularly in orchestrating a 19-point comeback, has underscored his potential value, presenting the Celtics’ front office with a complex decision point. The contest in Miami saw the Celtics, reeling from a two-game losing streak, fall behind by double digits early and face a 15-point deficit late in the third quarter, seemingly destined for a third consecutive defeat. However, Simons catalyzed a dramatic shift in momentum.

His five-point burst in the waning moments of the third quarter narrowed the deficit to 10 points heading into the final period. The fourth quarter became Simons’ stage, as he either scored or assisted on 17 consecutive Celtics points during a critical five-minute stretch. This included a pivotal step-back three-pointer that put Boston ahead permanently. The Heat deployed multiple defenders, but Simons’ ability to create offense with apparent ease proved insurmountable, allowing teammates such as Jaylen Brown to operate with reduced defensive pressure in other areas of the court.

After an initial period of adjustment and inconsistent play following his arrival from the Portland Trail Blazers, where he had spent the previous four seasons as a starter, Simons has demonstrated significant improvement and comfort within the Celtics’ system. His play throughout January has been particularly impactful, with averages of 18.3 points and 3.6 assists per game, coupled with efficient shooting splits of 49% from the field and an impressive 51.6% from beyond the arc. While his career trajectory previously centered on a starting role, his recent performances suggest a potent fit as a "microwave scorer" off the bench, providing instant offense.

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The statistical impact of Simons’ scoring is evident in the Celtics’ recent record. The team holds a 4-0 record when Simons reaches at least 25 points, and a 6-1 record when he scores 20 or more. Expanding further, Boston is 13-5 in games where Simons achieves 15 points, contrasting sharply with an 8-10 record when he falls below that mark. This data highlights his growing importance as a supplementary offensive engine, particularly in games where the primary scoring options might face heightened defensive attention or experience an off night.

The Case for Trading Simons

Several compelling factors contribute to the argument for the Celtics to consider trading Anfernee Simons before the February 5 deadline. Foremost among these is his contract status: Simons is currently on an expiring contract worth $27.6 million. This substantial figure makes him an attractive asset for teams seeking to shed salary or acquire a talented guard, while simultaneously positioning him as a valuable trade chip for Boston.

A primary motivation for moving Simons would be to address the Celtics’ pronounced need for frontcourt reinforcement. The offseason saw the departures of key big men Kristaps Porzingis, Al Horford, and Luke Kornet, leaving the team with a perceived void in depth, particularly in the areas of rim protection and rebounding. Reports from NBA insider Jake Fischer indicate that the Celtics have been "monitoring the big man market for potential trade options for some time," suggesting a strategic intent to bolster their interior presence. Acquiring a center or power forward with Simons’ contract could provide a direct pathway to upgrading this critical area, potentially bringing in a player who could contribute immediately to a championship pursuit.

Beyond roster construction, financial considerations play a significant role. While the Celtics’ offseason maneuvers successfully positioned them beneath the dreaded second apron of the luxury tax, the team remains approximately $4 million over the first apron and $12 million over the luxury tax line. Trading Simons’ substantial salary could offer the Celtics valuable flexibility, potentially allowing them to drop below the first apron or even the luxury tax threshold entirely. Such a move would mitigate future financial penalties and provide greater maneuverability in subsequent offseason periods.

Furthermore, if the Celtics’ front office does not envision re-signing Simons in the upcoming summer free agency, or if they anticipate being priced out of retaining him, trading him at the deadline becomes a prudent strategy. This would prevent the potential loss of a valuable asset for no compensation, instead allowing the team to acquire a future contributor, draft picks, or significant salary relief. Fischer also suggested that "the Celtics’ deadline business – whether they trade for a big man or not and how significant the trade is – should serve as a useful hint about their plans for an in-season comeback from Jayson Tatum." While Tatum’s return from a torn Achilles tendon has no definitive timeline, the six-time All-Star has expressed his intention to play this season. Should Tatum make an earlier-than-expected return, even in a limited capacity, the Celtics’ immediate need for Simons’ high-usage scoring might diminish, making a trade more palatable.

Despite his substantial contract, Simons’ relative youth at 26 years old and his proven scoring ability would likely generate considerable interest across the league. Teams seeking a dynamic bench scorer, or even a potential lead guard to develop, could view him as an appealing target.

The Case for Keeping Simons

Conversely, a strong argument exists for the Celtics to retain Anfernee Simons, particularly given the team’s current standing and his recent contributions. As the season approaches its midpoint, the Celtics boast a 25-15 record, placing them in a tie for second place in the Eastern Conference alongside the New York Knicks. This robust performance solidifies their status as a legitimate contender, making any move that could disrupt team chemistry or diminish offensive firepower a cautious consideration.

Given Boston’s championship aspirations, simply dumping Simons’ salary would be difficult to justify, especially in light of his recent pivotal role in securing victories. His emergence as a reliable secondary scorer has proven invaluable. Celtics President Brad Stevens publicly praised Simons last month, stating, "I’m a big fan, I like him a lot… He’s a quiet guy, but just a super person, and so he’s really come in with a great mindset: ‘I’m going to help the team any way I can.’ And offensively, he knows he’s capable of going nuts in any given game." This endorsement from the team’s president underscores Simons’ perceived value and character within the organization.

Throughout their recent tenure as contenders, the Celtics have frequently sought a player with Simons’ specific offensive profile: an ultra-quick guard capable of consistently beating defenders off the dribble, penetrating the lane, and collapsing opposing defenses. While Derrick White and Payton Pritchard offer elements of this skillset, neither possesses Simons’ exceptional quickness or athleticism. Retaining Simons for the playoffs would introduce a distinct offensive dimension, offering diverse options against various defensive schemes. The prospect of deploying small, high-octane lineups featuring Simons alongside White, Tatum, and Brown presents a formidable challenge for opposing teams, creating significant spacing and scoring opportunities.

Even with Jayson Tatum’s eventual return, Simons’ firepower could be an incredible luxury, providing an additional offensive threat alongside Boston’s two All-NBA talents, Tatum and Brown. This depth would be crucial for navigating the rigors of a deep playoff run.

Furthermore, keeping Simons through the end of the season does not automatically mean losing him for nothing in free agency. The Celtics could explore re-signing him to a more team-friendly contract in the summer, or potentially execute a sign-and-trade deal to acquire assets. Should Simons ultimately depart in free agency, his departure could open up the Non-Taxpayer Mid-Level Exception, as noted by cap expert Keith Smith. This exception would provide the Celtics with a valuable tool to add another contributor to their roster, offering a strategic alternative for team building.

A Position of Strength

The Boston Celtics find themselves in an enviable position as the trade deadline looms, largely thanks to their strong season performance and Anfernee Simons’ recent surge. The organization holds a "win-win" scenario. Should they elect to trade Simons for a big man, they would address a primary roster weakness in the frontcourt, potentially bolstering their interior defense and rebounding, while also achieving desired financial flexibility. Alternatively, retaining Simons ensures the presence of one of the league’s most effective bench scorers, adding a crucial layer of offensive depth and versatility for a championship contending team.

Regardless of the ultimate decision, the trajectory of Anfernee Simons and the Boston Celtics will undoubtedly be a focal point of observation leading up to and beyond the NBA trade deadline. The outcome will have significant implications for the team’s immediate title aspirations and its long-term roster construction.

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