Celtics trade for Anfernee Simons is weird (but bold): Instant reaction & analysis

The Boston Celtics just traded Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second-round picks, per Shams Charania of ESPN. Simons joins the Celtics following some impressive seasons in Portland that have seen him emerge as one of the better young scorers in the league. At just 26 years old, he is just now entering the prime of his career, and he’ll get the chance to do so in Boston.

Holiday joined the Celtics roughly two years ago in the wake of the Damian Lillard trade, shipped out by the Milwaukee Bucks and ending up in the hands of Boston thanks to the Blazers acting as the middleman. Since then, he’s made an All-Defensive team and helped the Celtics lift Banner 18.

Now, he enters the next part of his career, and the Celtics begin their roster reset heading into next season.

The second-round picks coming back to Boston in the trade are the New York Knicks' 2030 second-round pick and the Blazers' 2031 second-round pick, per Jake Fischer of The Stein Line.

What will Anfernee Simons bring to the Celtics?

Last season, Simons appeared in 70 games for the Blazers, playing 32.7 minutes per contest. He averaged 19.3 points, 2.7 rebounds, and 4.8 assists per game while shooting 42.6% from the field and 36.3% from beyond the three-point line.

At 26 years old, Simons is a career 38.1% three-point shooter and an impressive shot creator. He's been a lead ball-handler in Portland's backcourt for the past four years, peaking at 23.4 points per game in the 2023-24 season (in just 46 games).

What makes the trade for Simons weird is his play style. He's a score-first guard and high-volume shooter who is used to having the ball in his hands. Simons has also been a subpar defender up to this point in his career, which doesn't match the way the Celtics play.

On top of that, they still have Derrick White and Payton Pritchard on the roster, clogging up the backcourt a bit with three rotation-level guys.

But this is a solid bet on Simons as a player, if the Celtics choose to keep him.

If they can find a way to help Simons keep his efficiency up while also teaching him to play more off the ball (and improve defensively), he could turn into a legitimate piece for the Celtics moving forward.

Bobby Marks of ESPN explained how the deal helps the Celtics financially, too, and getting off of Holiday's long-term money is a good thing for Boston. (He later corrected it to *over* the second apron, not under.)

More information and analysis will be added here shortly.