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Celtics trade Jrue Holiday for Anfernee Simons

Originally posted on Ball Exclusives | By Titan Frey | Last updated Jun 24, 2025 8:41 AM ET

The Boston Celtics had a disappointing end to their 2025 season. With the injury to Jayson Tatum and a booming tax bill, changes were expected.

The first change occurred late last night when the Celtics traded defensive specialist Jrue Holiday to the Portland Trail Blazers. In return, Boston receives Anfernee Simons and two second-round draft 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 deal helps Boston in a few ways. For starters, it helps the Celtics get younger. Despite how good Holiday is, he is 35 years old. Simons, on the other hand, is 26 and has a bright future ahead of him.

Simons averaged 19.3 points per game this past season and 22.6 in the 2023-24 season. Boston will need a scoring boost with Tatum out.

More importantly, the Celtics clear up some cap space, as they owed Holiday $72 million in 2026-27 and 2027-28. Trading Holiday saves the Celtics $40 million in luxury tax payments for next season.

As for Portland, they reunite with Holiday, as they originally traded for him two years ago when they sent Damian Lillard to the Milwaukee Bucks. The Blazers only kept Holiday for four days before sending him to Boston in exchange for Malcolm Brogdon, Robert Williams III, and two future first-round draft picks.

Will Portland keep Holiday now? Or use him in another trade package?

This article first appeared on Ball Exclusives and was syndicated with permission.

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