Celtics make first big trade of NBA offseason

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.

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.