Sources: Celtics Trade Jrue Holiday to Trail Blazers

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

Portland moved quickly to re-sign Holiday, who was first acquired from the Milwaukee Bucks in the Damian Lillard trade in 2023 and then relocated to Boston.

Simons joins Boston on an expiring contract, while Holiday is owed approximately $72 million in 2026-27 and 2027-28.  According to ESPN's Bobby Marks, the agreement saves Boston $40 million in luxury tax payments for next season. 

Holiday is returning to Portland after being traded to Boston two years ago for Malcolm Brogdon, Robert Williams III, a 2024 first-round selection pick (later Bub Carrington), and a 2029 first-round draft pick.  Lillard's original package comprised Holiday, Deandre Ayton, Toumani Camara, a first-round selection, and two first-round pick swaps.

The trade kicks off what is likely to be an eventful summer for the Celtics, who are rebuilding their roster following Jayson Tatum's right Achilles injury in the second round of the playoffs.  According to insiders, they are still negotiating trades for several key players on the roster. 

Holiday won All-Defensive Team accolades in 2023-24, shooting a career-high 42.9% from three.  He contributed significantly to the team's championship run that season, averaging 13.2 points on 50-40-90 shooting splits.

Holiday, who is entering his 17th NBA season, provides championship experience to the Trail Blazers' young core.  He will also bolster Portland's improving defence.  

Simons gives the Celtics a 26-year-old scoring guard who can shoot from long range.  Simons has made roughly nine 3-pointers per game over the last three seasons, which is an essential talent in Celtics coach Joe Mazzulla's 3-point-heavy attack.