Boston Celtics May Trade Two Stars To Avoid Paying Massive Luxury Tax

The Boston Celtics are facing a financial dilemma that could force them to make some difficult roster decisions this summer. Despite sitting at 53-19 and once again looking like legitimate title contenders following last year’s championship run, the franchise’s future might involve breaking up key pieces of their core to avoid plunging deeper into luxury tax hell.

According to Zach Harper of The Athletic, Boston’s new financial reality under the NBA’s updated Collective Bargaining Agreement is creating pressure to shed salary. 

"They could start by trading Jrue Holiday this summer. It would bring them below the second apron and just above the first apron. It would greatly reduce that tax penalty, and they’d probably see enough flexibility to bring Horford and/or Kornet back on reasonable deals."

"But we’re still looking at the Celtics having to eventually break up parts of this team. It wouldn’t be shocking to see Kristaps Porzingis go soon, as he has one year left on his deal."

"As long as the Celtics continue to compete for and win titles, the fan base will be fine. The second that gets hamstrung, I’d imagine the new ownership will be under scrutiny. However, Chisholm is getting the team when it’s time for the money to hit the fan."

The Celtics’ projected financials are eye-popping. With 11 players already under contract for $225.2 million next season, they are expected to exceed the second apron threshold of $207.8 million. 

Factoring in tax penalties, their total payroll could hit a staggering $500 million. And that’s without re-signing Al Horford, Luke Kornet, or filling out the remainder of the roster. 

These numbers are simply unsustainable, especially with the new CBA punishing teams that repeatedly breach the second apron. Not only are certain trade and roster-building mechanisms restricted, but after two consecutive years above the threshold, Boston would be barred from trading its 2033 first-round pick.

Enter Jrue Holiday and Kristaps Porzingis—two vital contributors, but also two of the more expensive and expendable players on the roster given their age, contract situations, and potential trade value. Holiday, 33, has averaged a modest 11.0 points, 4.3 rebounds, and 3.8 assists this season while maintaining his trademark defense. 

Porzingis, on the other hand, has been far more productive, averaging 19.3 points, 6.8 rebounds, and 1.6 blocks while shooting efficiently from both the field (48.3%) and beyond the arc (39.1%). Still, with only one year remaining on his contract, his future in Boston is far from guaranteed.

The financial pressure is compounded by a recent ownership change. Bill Chisholm of Symphony Technology Group purchased the Celtics at a record $6.1 billion valuation, the highest in North American sports history. 

While Wyc Grousbeck will remain the team’s governor until 2028, Chisholm’s influence could begin reshaping the Celtics’ approach to roster building sooner than expected. Especially if the team begins feeling the strain of massive luxury tax penalties.

In a recent interview, Grousbeck made it clear that no team—no matter how successful—can sustain second apron spending long-term. 

This revelation sent shockwaves through Celtics Nation, essentially dampening any hopes of a long-term dynasty under the current core of Jayson Tatum, Jaylen Brown, Jrue Holiday, Kristaps Porzingis, and Derrick White.

The harsh truth is that even championship teams aren’t immune to the CBA’s constraints. 

The league wants parity and financial discipline, and the Celtics are the first true test case of a contender potentially needing to sacrifice elite talent for fiscal flexibility. Trading Holiday or Porzingis—or both—might not just be a cost-saving measure. It could be the only way to sustain success without crippling the team’s future flexibility.

Boston fans can take solace in the fact that their team is still winning. But as the dollars pile up, difficult decisions loom. The era of the all-in superteam might be nearing its end—and the Celtics could be its biggest casualty.