The Boston Celtics are trading Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round draft picks, sources told ESPN on Monday night.

Portland moved aggressively to reacquire Holiday, whom the franchise originally received from the Milwaukee Bucks in the Damian Lillard trade in 2023 and later moved to Boston.

Simons joins Boston on an expiring contract, while Holiday is owed around $72 million in 2026-27 and 2027-28. The deal saves Boston $40 million in luxury tax payments next season, according to ESPN’s Bobby Marks.

Portland receives Holiday back after trading him to Boston two years ago for Malcolm Brogdon, Robert Williams III, a 2024 first-round draft pick (that became Bub Carrington) and a 2029 first-round draft pick. The original package for Lillard included Holiday, Deandre Ayton, Toumani Camara, a first-round pick and two first-round pick swaps.

The move begins what is expected to be an active offseason for the Celtics, who are retooling their roster in the wake of Jayson Tatum’s right Achilles tear in the second round of the playoffs. They remain engaged in trade talks surrounding multiple key players on the roster, sources said.

Holiday earned All-Defensive team honors while shooting a career-high 42.9% from 3 in the 2023-24 season. He played a crucial role in the team’s run to the title that season, averaging 13.2 points on 50-40-90 shooting splits.

Holiday, now heading into his 17th NBA season, brings championship experience to a young Trail Blazers core. He will also help Portland’s rising defense. From Jan. 19 onward, the Trail Blazers had a 23-18 record and ranked third in the league in defensive rating and effective field goal percentage allowed in transition (58.2%), according to ESPN Research.

In Simons, the Celtics get a 26-year-old scoring guard who is comfortable shooting from distance. Simons has averaged nearly nine 3-point attempts per game over his past three seasons, a valuable skill in Celtics coach Joe Mazzulla’s 3-pointer-heavy offense.