The first domino of the Celtics’ offseason roster renovation 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 his sixth career All-Defensive selection, shot a career-best 42.9% from 3-point range and was one of Boston’s top playoff performers, his impact peaking during the Eastern Conference finals against Indiana. The veteran’s numbers then declined across the board during the 2024-25 campaign while he battled injuries that sidelined him for 20 regular-season games and three playoff games.
Still, teammates routinely raved about his talent and penchant for winning plays.
“What Jrue does for us, it’s elite,” big man Al Horford said after a first-round win over Orlando that Holiday missed with a hamstring injury. “The impact that he has on our team, you can’t measure it.”
Holiday said after the season that he hoped to remain with the Celtics.
“I think we still have a really, really great opportunity and a great window to win a championship again,” he said on May 17. “I think the talent that we have on this team, not only on the court, but the coaching staff, all the way up to Brad (Stevens), has been amazing. So the opportunity to win is now, and I still want to be a part of that.”
It was speculated that 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, Boston’s president of basketball operations was able to land an impressive return in Simons, who just turned 26 and was a productive offensive player during his seven-year tenure with the Trail 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’s one of the NBA’s highest-volume 3-point shooters — his 593 attempts from deep this season ranked 13th in the league, and his 215 makes ranked 17th — which should make him a good fit for head coach Joe Mazzulla’s bombs-away philosophy.
Boston set NBA records for 3-point makes and attempts this season, with Derrick White, Payton Pritchard and Jayson Tatum all ranking in the top 12 in both categories.
The Celtics are accepting a defensive downgrade in the trade, however, as Simons isn’t nearly as skilled as Holiday at that end of the floor. Opponents shot 50.6% from the floor this season when guarded by Simons, per NBA player tracking. Every Boston rotation player had a lower defensive field-goal percentage, with Holiday — who’s regarded as one of the NBA’s top perimeter defenders — checking in at 44.4%.
Drafted 24th overall out of high school in 2018, Simons also has dealt with injuries throughout his career — 25 games missed in 2021-22, 20 in ’22-23, 36 in ’23-24 — but started 70 games this season for a young Blazers squad. One of his most productive outings of the season came at TD Garden on March 5, when he tallied 30 points and six assists in a 128-118 loss to the Celtics, who got a combined 84 points from Simons’ new backcourt mates, White and Pritchard.
Simons is entering the final year of a four-year, $100 million contract and is set to earn $27.7 million this coming season — approximately $4.7 million less than Holiday’s 2025-26 salary. The Celtics still sat well above the second apron of the NBA’s luxury tax following the trade, so additional moves likely are forthcoming.
Center Kristaps Porzingis and reserve sharpshooter Sam Hauser are two other obvious trade candidates if Boston is looking to shed additional salary. Key cogs like Jaylen Brown and White would carry higher trade value, but multiple reports indicated the Celtics would prefer to keep both. The extent to which Stevens is willing to reshape his roster following Jayson Tatum’s season-ending Achilles tear remains unclear.
Flipping Simons in a subsequent move is another possibility for Boston.
The second-round picks the Celtics received in Monday’s deal are in 2030 and 2031, per a report from MassLive.com’s Brian Robb. The 2025 NBA Draft, in which the C’s own the 28th and 32nd overall selections, begins Wednesday.
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