BOSTON — The first domino of the Celtics’ offseason roster retool fell late Monday night.

Boston traded guard Jrue Holiday to the Portland Trail Blazers for guard Anfernee Simons and two second-round draft picks, according to a report from ESPN’s Shams Charania.

Holiday, who turned 35 earlier this month and has three years and more than $100 million remaining on his contract, was viewed as one of the Celtics’ most logical offseason trade candidates. His arrival in 2023 (from Portland, which had acquired him from Milwaukee days earlier) was a vital step in Boston’s path to the NBA championship last season.

In his first season with the Celtics, Holiday earned second-team All-Defensive honors, shot a career-best 42.9% from 3-point range and was one of Boston’s top playoff performers. The respected veteran’s numbers declined across the board this past season while he battled injuries that sidelined him for 20 regular season games and two playoff games.

It was speculated that Celtics president of basketball operations Brad Stevens — whose team must shed roughly $20 million in salary this offseason if it hopes to avoid steep second-apron penalties — might need to attach a draft pick in order to offload Holiday’s hefty contract. Instead, he was able to fetch an impressive asset in Simons, who just turned 26 and put up solid numbers during his seven-year tenure with the Blazers.

Since becoming a full-time starter three years ago, Simons has averaged 20.7 points and 4.7 assists per game while shooting 43.4% from the field and 37.4% from three. He was drafted 24th overall out of high school in 2018.

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