Apr 20, 2025; Boston, Massachusetts, USA; Boston Celtics guard Jrue Holiday (4) reacts after a play during the second against the Orlando Magic at TD Garden. Mandatory Credit: Bob DeChiara-Imagn Images Bob DeChiara-Imagn Images

Celtics Send Jrue Holiday to Trail Blazers in Massive Blockbuster Trade

Originally posted on Boston Celtics on SI | By Jason Fray | Last updated Jun 23, 2025 11:58 PM ET

Even though the 2025 NBA Finals have come to a close, the landscape of the league is arguably about to become a whole lot busier.

The Boston Celtics signaled as much Monday evening, as the C's shockingly dealt Jrue Holiday to the Portland Trail Blazers in a deal that netted them young guard Anfernee Simons. The Celtics also received two second-round picks in the deal.

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Boston is facing a bit of an uphill climb in 2025-26. With star Jayson Tatum presumably missing all of next year with a torn Achilles, coupled with the ownership change, the team was set to retool considerably in the offseason around Jaylen Brown.

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

Holiday was a name rumored to be on the move for weeks. The former UCLA star has developed into a proven commodity capable of helping any team win an NBA Title. At the same time, Boston clearly wanted to cut salary and readjust accordingly.

Holiday had inked a four-year extension last year with the Celtics worth $135 million. As it stands now, Boston was able to get out from under that deal with the Blazers picking up the final two years of Holiday's contract (worth $67.5 million). Holiday's age (he just turned 35) likely contributed to Boston's desire to move him as well.

The deal enables Boston to get under the second apron and avoid paying heavy taxes. At the same time, the Celtics get Simons — a promising young guard in the final year of his deal. Presumably, Boston could re-sign Simons if its deemed a good fit between both parties this season. Additionally, Simons could just walk after the year which would free up some cap space.

Additionally, Boston could trade Simons during the season to further recoup assets.

Portland's motivation likely stems from getting a rock-solid veteran that can help mentor the young players on its team. While it's too soon to concretely declare a winner in this deal, the Celtics have to be thrilled in getting off Holiday's contract for a far younger and potentially more talented player for a fraction of the price.

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