Report: Celtics deal Jrue Holiday to Blazers for Anfernee Simons, picks

The Portland Trail Blazers are reacquiring two-time All-Star guard Jrue Holiday from the Celtics, sending guard Anfernee Simons and two future second-round draft picks to Boston in return, ESPN reported on Monday night.
Holiday, 35, who will earn $32.4 million next season, is owed a total of approximately $72 million in 2026-27 and 2027-28, after which his four-year, $134.4 million contract that he signed with the Celtics in April 2024 expires.
Meanwhile, the 26-year-old Simons joins the Celtics on an expiring contract. Per ESPN, the deal saves Boston $40 million in luxury tax payments next season.
In 2023, Portland landed Holiday in a deal with the Milwaukee Bucks for Damian Lillard, then sent the 16-year veteran to Boston and acquired a pair of first-round picks. Holiday never played a game for the Blazers.
Per the report, the Celtics are actively involved in trade talks involving multiple players on their roster following Jayson Tatum’s Achilles tear in the second round of the playoffs.
In his first season with the Celtics, Holiday played an instrumental role in the team’s run to the NBA title, shooting a career-high 42.9 percent from 3-point range in 2023-24 and earning All-Defensive team honors.
Holiday was a first-round pick (No. 17 overall) of the Philadelphia 76ers in 2009. He has career averages of 15.8 points, 6.2 assists, 4.2 rebounds and 1.4 steals with the 76ers (2009-13), New Orleans Pelicans (2013-20), Bucks (2020-23) and Celtics in 1,037 games (956 starts). He won his first NBA title with Milwaukee in 2021 and is a six-time All-Defensive selection.
Simons, 26, was also a first-round selection, picked at No. 24 by the Blazers in 2018. In seven seasons with Portland he posted 15.0 points, 3.3 assists and 2.5 rebounds over 389 games (213 starts). He should fit in with the Celtics’ offensive approach, as he has averaged nearly nine 3-point attempts per game the last three seasons and is a career 38.1 percent shooter from distance.