Celtics Trading Jrue Holiday To Blazers For Anfernee Simons, Second-Rounders

The Boston Celtics have taken the first step to reshaping the roster following the Achilles injury to star wing Jayson Tatum.

Per Shams Charania of ESPN, the Celtics are doing this by sending veteran guard Jrue Holiday to the Portland Trail Blazers for guard Anfernee Simons and two second-round draft picks.

Holiday was actually acquired by the Celtics from the Blazers (via the Milwaukee Bucks) before the start of the 2023-24 season — then became a key member of the Celtics’ championship run. He owns two championship rings and will bring a needed veteran presence to a Blazers team that is aiming for a playoff push next season. 

“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 the Blazers,” Charania wrote.”Simons joins Boston on an expiring contract.”

Holiday, 35, appeared in 62 games for the Celtics this season, averaging 11.1 points, 4.3 rebounds and 3.9 assists. In the 2025 postseason, he averaged 10.3 points, 4.1 rebounds and 4.1 assists in seven games against the Orlando Magic and New York Knicks.

Simons, 25, had been linked to the Magic and several others, but this deal took some around the league by surprise. He averaged 19.3 points and shot 36.3 percent on 3-pointers this past season.

Per Jake Fischer of The Stein Line, the Celtics are receiving a 2030 Knicks second-rounder and a 2031 Blazers second-rounder from Portland.