The Boston Celtics' season has turned out much differently than anticipated, and that will likely be reflected come the 2026 NBA trade deadline on Feb. 5. The Celtics came into the year without their best player, Jayson Tatum. The six-time All-Star tore his achilles tendon in last year's playoffs, forcing him to sit out this year. Because of that, the Celtics underwent a mini-rebuild in the offseason.
Highly paid and important players such as Kristaps Porzingis and Jrue Holiday were traded in an effort to get the team's finances in check ahead of a year where they weren't expected to contend. Al Horford was let go in free agency, too, and it became clear that Boston was going to give opportunities to younger players. Many called this a gap year, and the expectations were that Boston would contend again once Tatum was healthy in 2026-27.
Instead, the Celtics have been one of the surprise teams of the season. Boston is still in second place in the Eastern Conference standings, and they could certainly push for an NBA Finals appearance even without Tatum, especially because other teams out East are either disappointing or have injury problems of their own. Jaylen Brown has become a megastar, and the role players have stepped up their games.
Earlier in the season, many thought the Celtics would be trade deadline sellers, and that they would continue moving off of contracts and players who might not be a part of their foreseeable future. Anfernee Simons is one such example. He was added in the Holiday trade. While he is cheaper and younger than Holiday, he is on an expiring contract, so many thought the Celtics would move him for even more future capital before he has the chance to bolt in free agency.
The Celtics' success has turned their trading philosophy on its head, though, and now they need to keep Simons. Trading the ex-Portland Trail Blazers guard would be a nightmare trade deadline scenario because it would hurt their chances to reach the NBA Finals this year in what has been a surprisingly successful season.
Trading Anfernee Simons would be a trade deadline nightmare
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Boston Celtics guard Anfernee Simons (4) reacts as his dribbles the ball against Detroit Pistons guard Cade Cunningham (2) in the first half at Little Caesars Arena.
Rick Osentoski-Imagn Images
Simons is still the most likely Celtic to be moved. While moving him made sense at one point, it would be a mistake with where the team is now. Boston should hold onto Simons even if it means losing him in free agency. The guard who entered the NBA straight out of IMG Academy has served as the team's sixth man spark plug.
He is averaging 14 points per game and shooting 40.2% from deep off the bench. These impressive numbers come despite the fact that he got off to a slow start. Simons is a perfect fit for what the Celtics do on offense. He can process defensive reads quickly and react by swinging the basketball to teammates or by launching shots from beyond the arc. Without him on the roster, Boston's championship odds would greatly diminish.
The former first-rounder could potentially even contribute on the team once Tatum is back. He is just 26 years old, so he definitely fits the team's timeline. Simons averaged 22.6 points per game just two seasons ago. While playing for the Celtics means sacrificing numbers for the betterment of the team, Boston could have peace of mind knowing they have a premier scorer on their roster who can produce much more than the average bench player.
Ducking the second apron was a priority for Boston this year, but they may be willing to re-sign Simons and spend big in the years to come, as they've done in previous years. The only context in which it would be okay to trade Simons is if they received a comparable player in return. Said player would need to be on a multi-year contract and, therefore, be able to both continue in helping the team this year and remain a part of the team's long-term plans. Preferably, this player would be a center. In all likelihood, though, a trade involving Simons would likely net the team lesser players and future draft capital. The Celtics need to hold onto Simons at this year's trade deadline.