Jrue Holiday out, Anfernee Simons in.
The Celtics made a major change to their backcourt late Monday night, reportedly trading Holiday to the Portland Trail Blazers in exchange for Simons and two future second-round draft picks.
Offloading the three years and $104 million remaining on Holiday’s contract was a big win for Boston as it looks to shed salary from its uber-expensive roster, and it was able to do so while also adding an intriguing, in-his-prime starter in Simons.
The 26-year-old won’t come close to matching Holiday’s talents as a defender — he’s a below-average player at that end of the floor, with an opponent field-goal percentage this season (50.6%) that would have ranked last among all Celtics rotation players — but could provide a jolt of offensive production to a Boston team that will be without top scorer Jayson Tatum for the foreseeable future.
In his three seasons as a full-time starter in Portland, Simons averaged 20.7 points and 4.7 assists per game, leading the Blazers in scoring since Damian Lillard departed for Milwaukee in 2023. The 6-foot-4 combo guard’s offensive game is well-suited for Joe Mazzulla’s 3-point-heavy approach, as he’s a career 38.1% shooter from deep and regularly ranks among the league’s most prolific long-range threats.
Simons — the first starting-caliber player Boston has added since the 2023 offseason — finished top-10 in the league in made 3-pointers per game in 2021-22 (10th), ’22-23 (seventh) and ’23-24 (sixth) before slipping to 17th this season. Over those four seasons, only Stephen Curry, Klay Thompson, Damian Lillard, LaMelo Ball, Luka Doncic and Donovan Mitchell averaged more made threes per game than Simons. Tatum, who’s expected to miss much of the upcoming season while he recovers from Achilles surgery, sits just behind him on that list.
Simons is reliable at the foul line, too, with a career free-throw percentage of 88.0%. His 90.2% mark this season (on 2.8 attempts per game) was fourth-best among qualifiers behind Curry, Lillard and Coby White.
Based on his resume, Simons should be an offensive upgrade over Holiday, who’s coming off a season in which he posted his lowest scoring (11.1 points per game) and assist (3.9) averages since his rookie year in 2009-10. Holiday also saw his 3-point effectiveness plummet in his age-34 season, dropping from a career-best 42.9% during Boston’s 2023-24 championship season to 35.3%.
It will be interesting, though, to see how Mazzulla schemes around Simons’ defensive issues following the breakup of one of the league’s stingiest guard pairings — Holiday and Derrick White. Third guard Payton Pritchard also is an offense-first player, though he’s made significant strides as a defender during his Celtics tenure.
Simons is well below Holiday’s level as a rebounder, as well, especially on the offensive glass. This season, he ranked in the eighth percentile for his position in offensive rebounding rate off missed field goals, per Cleaning the Glass. Holiday was in the 79th percentile — and ranked even higher in each of the previous six seasons.
From an on-court perspective, Boston essentially is swapping out Holiday’s dirty-work ability for Simons’ offensive upside, though the latter will need to prove he can stay healthy to reach his potential. He’s missed a total of 175 games over seven seasons since being drafted 24th overall out of IMG Academy in 2018, though he was able to play and start 70 in 2024-25.
And all of this assumes Simons is still with the Celtics when the new season tips off in October, which is no guarantee. Though his swap for Holiday increased Boston’s long-term financial flexibility, it shaved just $4.7 million off the roughly $20 million the team must clear if it hopes to dip below the second apron of the NBA’s luxury tax this offseason.
Simons’ expiring contract, which will pay him $27.7 million for the upcoming season, could be moved again in a subsequent trade as the Celtics continue their quest to cut costs and avoid the worst of the league’s tax penalties, which include both steep financial sanctions and severe restrictions on the types of trades and signings second-apron teams are allowed to make.
If the Celtics do choose to keep Simons, they’ll likely ship out at least one more player from their title-winning core. Center Kristaps Porzingis and wing Sam Hauser both appeared in fresh trade rumors in the wake of the Holiday deal, with The Stein Line’s Jake Fischer listing the San Antonio Spurs and Phoenix Suns as potential Porzingis suitors and Sports Illustrated’s Chris Mannix reporting Hauser “has generated strong interest.”
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