For weeks, there have been rumors that the Boston Celtics would need to trade several members of their championship core. Still, them trading Jrue Holiday to the Portland Trail Blazers the day after the NBA Finals came as a huge surprise.
The Celtics pulled off a late-night trade with the Blazers that sent Holiday to Portland in exchange for Anfernee Simons and two second-round picks.
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
The move was largely to save salary for the Celtics. While it only saved them $4.7 million this season, it will save them $72 million in salary over the next two years and $40 million in luxury tax in 2025-26, according to ESPN insider Bobby Marks.
For Portland, they get a veteran player who has won two championships and is still one of the best defensive players in the NBA. Still, he is so much older than their young core. Even so, considering that the Blazers were better than expected last season, adding him is a clear sign that they plan to make a push for the play-in tournament next season.
Who won the Jrue Holiday trade: the Celtics or the Blazers?
The Celtics get one of the best high-volume shooters in the NBA in Simons while saving an arm and a leg in both long-term salary and luxury tax payments. Not only that, but he is almost 10 years younger than Holiday, which makes them far younger than they were last season.
He is also under contract for another year, giving them a chance to see how he looks in the Celtics uniform before having to commit long-term to them. It's hard not to see this as an absolute win for Boston.
That's not to say that the Blazers lost the trade, but it's interesting that they couldn't get more value for Simons considering his age, contract, and reputation as a sharpshooter. Then again, starting point guards aren't nearly as hard to find as they once were.
It's a short-term play for the Blazers, who likely acquired Holiday partly to mentor former number three overall pick Scoot Henderson. If he can help Henderson grow as a point guard and help the Blazers take the next step in their rebuild, then it would be a solid move for Portland.
Holiday appears likely to retire after the end of his contract, with him having two years left on his deal. That would take him up to his 18th season, and there is definitely a risk of him declining during those two seasons. Not getting an asset from Boston and having to give up two seconds is a bit of a head-scratcher and will affect their trade grade.