The Boston Celtics are parting ways with a core member of their 2023-24 NBA championship squad, as ESPN reported Monday the team has agreed to trade two-time All-Star guard Jrue Holiday to the Portland Trail Blazers for high-scoring guard Anfernee Simons. 

Boston will also receive two second-round draft picks in exchange for Holiday, a six-time member of the NBA's All-Defensive Team and a key part of the Celtics' run to their most recent NBA title.

The move enables Boston to reduce its luxury tax bill for next season. Holiday is due a $32.4 million salary in 2025-26 and a guaranteed $34.8 million the following season, while Simons will earn $27.7 million in the final year of his current contract.

Boston also adds a useful offensive piece in Simons, who averaged 19.3 points in 70 games last season and 20.7 points per game over his last three campaigns. The 26-year-old is a career 38.1 per cent shooter from 3-point range.

The Celtics set NBA records for 3-pointers made (1,457) and attempted (3,955) this past season, in which they finished second in the Eastern Conference with a 61-21 record but lost in six games to the New York Knicks in the second round of the playoffs.

BREAKING: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN. pic.twitter.com/2ycXQicGkT

— Shams Charania (@ShamsCharania) June 24, 2025

Boston was also in need of additional scoring help with superstar Jayson Tatum expected to miss a large portion of next season after rupturing his Achilles tendon in Game 4 of its playoff series against the Knicks.

Holiday, entering his 17th NBA season, brings a desired veteran presence to a rebuilding Blazers team that has missed the playoffs in four straight seasons but took a step forward in 2024-25. Portland improved its win total from 21 in 2023-24 to 36 last season and compiled a 22-18 record since Jan. 23.

The 35-year-old averaged 11.1 points, 4.3 rebounds, 3.9 assists and 1.1 steals in 62 games last season.

This is the second time the Blazers have acquired Holiday in an offseason blockbuster trade. He was part of the package Portland received from Milwaukee in the September 2023 deal that sent franchise icon Damian Lillard to the Bucks, though Holiday was then traded to Boston four days later without playing a game for the Blazers.

Holiday also won an NBA title with the Bucks in 2020-21 and was a member of the United States' gold medal-winning teams at both the 2020 Tokyo Summer Olympics and the 2024 Paris Games.