Sources: Celtics trading Holiday to Trail Blazers

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 re-acquire Holiday, whom the franchise originally received from the Milwaukee Bucks in the Damian Lillard trade in 2023 and later moved to Boston in a deal that netted the Blazers two first-round picks.

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.

The move begins an extremely active offseason for the Celtics, who are retooling their roster in the wake of Jayson Tatum's 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 made his impact in Boston felt immediately, earning 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 year, 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 that includes a young point guard in Scoot Henderson.

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