After winning the NBA Finals in 2023-24, the Celtics returned with the same squad for the 2024-25 season. With its talent on the roster, Boston found itself in the second apron of the luxury tax. 

Boston’s season ended in the 2025 playoffs, and change is expected this offseason. On Monday evening, the Celtics made their first big move. ESPN’s Shama Charania reported that Boston is trading Jrue Holiday to the Portland Trail Blazers. In that deal, Boston also received SG Anfernee Simons and two second-round picks. Charania noted that Boston remains “engaged” in trade talks after moving Jure Holiday.

NBA insiders anticipate the Celtics making more trades this offseason

Portland makes an aggressive move to re-acquire Holiday, who the franchise originally received from Milwaukee in the Damian Lillard trade in 2023 and later moved to Boston for a deal that included two first-round picks to Blazers. Simons joins Boston on an expiring contract. https://t.co/2TMs5Cd8qn

— Shams Charania (@ShamsCharania) June 24, 2025

This is the second time in the last two seasons the Trail Blazers have acquired Jure Holiday. Ahead of the 2023-24 season, the Bucks and Trail Blazers were involved in a trade. Damian Lillard was sent to Milwaukee, and Jrue Holiday to Portland. However, the Celtics traded Robert Williams, Malcolm Brogdon, and two second-round picks to acquire Jrue Holiday. That turned out to be a worthwhile move for Boston.

Holiday had championship experience and helped the Celtics win the 2024 NBA Finals. After two seasons in Boston, the team had traded Holiday to the Trail Blazers. The 2025-26 season will be the two-time champion’s 17th professional season. Holiday started 62 of Boston’s 82 games in 2024-25. Over the next two seasons, Jrue Holiday is owed roughly $72 million.

The Celtics made this deal to save themselves $40 million in luxury tax for next season, according to ESPN’s Bobby Marks. NBA insiders reported that Boston will remain “engaged” in trade talks this offseason. They are retooling their roster for 2025-26, knowing Jayson Tatum will miss a majority of the year. In the deal with Portland, the Celtics acquired Anfernee Simons on an expiring contract.

Simons was the 24th overall pick by Portland in the 2018 NBA draft. The 26-year-old had been a full-time starter over the last three seasons for the Trail Blazers. Anfernee Simons should make a smooth transition to Boston. The team shot (47.2) three’s per game last season to lead the NBA. With Portland, Simons averaged 8.5 three-pointers attempted per game. The young SG is athletic and could be a starter for Boston next season. What will be the next move for the Celtics?

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