It took one day after the Oklahoma City Thunder hoisted the Larry O’Brien Trophy for Brad Stevens to make the Celtics first move of the offseason, trading Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons.
In 70 games last year, he averaged 19.3 PPG, 4.8 AST, and 2.7 REB on 43% from the field, 36% from three, and 90% from the free throw line. He took a small step back last season statistics wise but he just turned 26 years old and is about to enter the prime years of his career.
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
Simons is an electric offensive player with the ball in his hands. He is able to create his own shot which is something the Celtics are desperately going to need this season with Jayson Tatum most likely missing the entire season. He is also a high flyer as he won the Slam Dunk Contest in 2021 and has some poster dunks on his resume that are pretty impressive at only 6’3”. Simons is also an elite three point shooter with a career three point percentage of 38% who should thrive in the Celtics offense.
One of the biggest knocks on Simons game is his defense as he is not very strong on that side of the ball. Every year of his career, Simons has been a below league average defender even with a slight improvement last season. Some of that can be chalked up to playing on a team in Portland who wasn’t winning many games, but that doesn’t tell the whole story as Simons is normally a target on defense for opposing teams.
A good example of his defensive struggles came against the Celtics on March 5th, 2025 when Derrick White and Payton Pritchard combined for 84 points and most of those came on plays where Simons was the primary defender.
Simons is not the typical guard you think of when you think of the Celtics, but I think he has potential to be a legit piece with the Celtics. Offensively, he should fit in pretty well in the Celtics three-point heavy offensive system and can be another ball handler who can create his own shot alongside Jaylen Brown, Derrick White, and Payton Pritchard.
On the defensive end, I think with mentorship from Derrick White, Joe Mazzulla and the Celtics coaching staff can do enough to make him at least a league average defender. He graded out well in the advanced stats for defense in the 2022-23 season, so maybe Boston can tap into that potential.
There is a realistic possibility that the Celtics flip Simons in another deal before the end of the offseason or let him go in free agency since he is on an expiring contract but I still like the idea of him in green. Welcome to Boston, Anfernee!
