Fresh off a turbulent summer that saw them flip key veterans after losing Jayson Tatum to a torn Achilles, the Boston Celtics are expected to continue making financially driven moves. The front office has found the moves to tuck themselves below the second apron, but will be expected back on the chopping board when it comes time to contend again.
That may see a number of trades happening in the 2026 offseason, with the likes of Xavier Tillman and Anfernee Simons expected to emerge as the prime candidates. There are several reasons why both players have been consistently linked to exits already.
Anfernee Simons
Anfernee Simons’ trade value hinges on both his current contract, an expiring $27.7 million deal, and his offensive talent. A career 38.1% shooter from deep and an elite scorer with an average of 19.9 points per game over the last four seasons per Basketball Reference, Simons could thrive in Boston’s pace-and-space system.
However, Simons, who signed a $100 million contract with Portland in 2022, is approaching free agency next summer, and Boston’s cap-conscious leadership sees his contract more as a movable asset than a building block. While the player may fit well in Joe Mazzulla’s high-volume three-point system, his defensive limitations and injury history cloud his future.
The Celtics originally traded Holiday to acquire Simons, effectively executing a salary dump. But reports state that Boston may simply be holding Simons as a placeholder, with the front office ready to flip him again for a frontcourt upgrade. He can be expected to be the first one on the trade block next offseason.
Xavier Tillman
Xavier Tillman, another key figure from Boston’s 2024 title run, faces a very different situation. Entering the final year of a two-year, $4.7 million deal, Tillman is in a make-or-break season after an underwhelming 2024-25 campaign. The 26-year-old forward appeared in just 33 games, averaging a mere point in seven minutes per game.
This steep drop in production is alarming given that Tillman had played a vital rotational role after arriving from Memphis midway through the 2023-24 season. That year, he logged 18.1 minutes per game and became a reliable piece during Boston’s playoff push. But with his usage plummeting last season, his future in green is murky.
The Celtics’ limited frontcourt depth might give him opportunities to contribute in the 2025-26 season, but if he fails to capitalize, he could be trade bait before the February deadline.
At the end of the day, Boston holds the leverage with both players. Simons’ contract gives them a valuable expiring deal to use in a larger trade, especially if a big man becomes available early in the season.
Tillman, on the other hand, has to prove his worth just to stay in the rotation. If neither player fits into the long-term picture, the Celtics might not hesitate to flip them.
