The Boston Celtics enter the pivotal trade season facing a dilemma. On one hand, they’re having an encouraging season (15-11) with playoff hopes, especially with Jayson Tatum’s pending return. On the other, financial pressure forces them to cut at least $12.1 million in salary to duck below the luxury tax and avoid the dreaded repeater tax in future years. This is a tightrope walk between short-term ambition and long-term financial health.
Bleacher Report recently listed the Celtics’ three most appealing assets: Derrick White, Payton Pritchard, and Jordan Walsh. However, sources indicate it’s highly unlikely any of the three are moved.
Derrick White is highly valued by the front office for his defense and ball-handling.
Payton Pritchard is having a breakout year (16.7 points, 5.0 assists) on a bargain contract (4 years, $30 million).
Jordan Walsh is an emerging 3-and-D wing, shooting 48.8% from deep on a minimal salary ($2.2 million).
Trading any of them would weaken the present and future roster, contradicting Brad Stevens’ “retooling” goal.
The most plausible path to salary relief is through Anfernee Simons ($27.6 million, expiring) or Sam Hauser (first year of a 4-year, $45 million deal). These are the names expected to be on the move.
However, both present challenges:
Sam Hauser is having a career-worst year, with his three-point percentage plummeting to 34.0%. Finding a taker for a slumping shooter on a long-term deal is a major hurdle.
Anfernee Simons’ massive $28 million expiring contract forces teams to carefully consider his rental value.
The Celtics may need to attach additional assets (like draft picks) or accept less value in return to facilitate a deal.
Recent losses to Milwaukee and Detroit are reminders that despite solid play, the Celtics aren’t yet true title contenders. This reinforces the stance of prioritizing long-term financial health over a half-hearted playoff push.
Brad Stevens faces the test: he must find a way to cut salary without overly weakening the current roster to still compete for a playoff spot, all while maintaining the build around Jayson Tatum and Jaylen Brown for the coming years.
This trade deadline will test Brad Stevens’ wisdom as an executive. He must perform a financial tango on a thorny dance floor: one step is ambition, the other is fiscal discipline. The final decision on who leaves (Simons or Hauser) and at what cost will shape not only the remainder of the 2025-26 season but also the Celtics’ flexibility for many summers to come.