Celtics make first big trade of NBA offseason

Oct 8, 2023; Boston, Massachusetts, USA; Boston Celtics guard Jrue Holiday (4) dribbles up the court during the first half against the Philadelphia 76ers at TD Garden. Mandatory Credit: Eric Canha-USA TODAY Sports

The Boston Celtics ended the first day of the NBA offseason with a bang.

The Celtics are reportedly trading point guard Jrue Holiday to the Portland Trail Blazers in exchange for combo guard Anfernee Simons and two second-round picks. ESPN’s Shams Charania broke the news on Monday night.

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 signals the Celtics’ intention to cut costs amid a ballooning luxury tax bill. Last season, the team signed Holiday to a four-year, $135 million contract extension that would have kept the guard in Boston until 2028. With Jayson Tatum potentially out the entire 2025-26 campaign, the decision to move Holiday is far from surprising.

Simons makes $27.7 million next season before becoming an unrestricted free agent. While the 26-year-old offers a higher offensive ceiling than Jrue, Simons is considered a major liability on defense. In 70 games last season, Simons averaged 19.3 points and 4.8 assists on 42.6% shooting from the field.

The trade cuts the Celtics’ luxury tax bill by around $40 million and gets them about $18 million below the second apron.

Here are the salaries going out

To Boston

Anfernee Simons: $25.9M, $27.7M (UFA, 2026)

* The Celtics get off the combined $72M owed to Holiday in 2026-27 and 2027-28

* Projected $40M in tax savings in 2025-26

* $18M over the 2nd apron

* Simons is extension eligible

To…
— Bobby Marks (@BobbyMarks42) June 24, 2025

The Celtics paid a much steeper price when they originally acquired Holiday from the Blazers in the 2023 offseason. Boston shipped out Robert Williams, Malcolm Brogdon, and two first-round picks to Portland. The Blazers later dealt one of the picks and Brogdon to the Washington Wizards for Deni Avdija.

Based on previous reports, Boston may not be done dealing just yet. There is widespread belief that the Celtics will look to trade one more All-Star player this offseason.