Breaking: Celtics trade Jrue Holiday for Anfernee Simons

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.

Related: Celtics’ Jayson Tatum has successful surgery on Achilles tendon

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.

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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?

About the Author Published Jun 24, 2025

TITAN FREY

Titan Frey is a dedicated father to three wonderful children, whom he takes immense pride in. His passions include reading, writing, basketball, both playing and watching, and playing chess. Titan spent five years working as a journalist for the basketball website fadeawayworld.net, where he served as editor-in-chief for four and a half years. One of his most notable achievements was interviewing Chuck Cooper III, the son of Chuck Cooper, the first African American ever drafted by an NBA team, and writing a biography that has been praised as the most definitive article about Cooper’s legacy. Titan is the author of more than ten novels and the screenwriter of three produced short films. His newest young adult novel, Echoes of the Hardwood: Braxton Foxworthy’s Time‑Travelling Book Report, blends basketball history with heartfelt storytelling and is now available. Order here: https://a.co/d/bo7BYz1