Boston Celtics fans, take a deep breath—things just got complicated but potentially brilliant for the Celtics. In a surprising turn, Jrue Holiday is heading out, Anfernee Simons is coming in, and Boston just opened up a massive $40 million in tax relief. Holiday played a crucial role in helping the Celtics hang Banner 18 just last season. But with the team staring down the barrel of an increasingly brutal luxury tax situation, something had to give. And as much as Holiday brought to the court, the front office was forced to make a tough financial call to keep their championship window open without going all-in on future penalties. But here’s the kicker:
Boston’s luxury tax bill for 2025-26 drops by a projected $40 million, thanks to unloading the $72 million still owed to Holiday over the next two seasons, per Bobby Marks. Now, that’s not just a minor trim—it takes the Celtics $18 million below the dreaded second apron, opening doors that many top contenders can’t even peek through.
Shams Charania broke the news: “The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN.“
BREAKING: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN. pic.twitter.com/2ycXQicGkT
— Shams Charania (@ShamsCharania) June 24, 2025
Simons, who averaged 20.7 points and 4.7 assists over the last three seasons, arrives on an expiring deal and is extension-eligible—a rare win-now and future play for Boston. The financial windfall is clear: swapping Holiday’s escalating salary for Simons’ $25.9 million contract not only saves the Celtics $40 million in tax but also positions them to maneuver under the NBA’s new cap landscape. The Celtics’ championship window just got a little wider—and a lot cheaper.
This is a developing story.
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