It's not a surprise that the Boston Celtics kicked off the NBA offseason with a trade — but it is rather surprising what that trade actually entails. Late on Monday night, the Celtics traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, according to Shams Charania of ESPN.
Simons is about to enter the final year of a four-year, $100 million contract, so he will likely be a one-and-done for the C's; but for a team that needed to regroup after potentially losing its superstar Jayson Tatum for all of next year, Simons' scoring punch will be a pretty massive boost alongside Jaylen Brown. He's not a household name, but Simons is a phenomenal shooter (38.1 percent for his career) and can catch fire at the snap of a finger (18 games of 30-plus points the past two seasons.)
Trade grades: Celtics add another offensive weapon in Simons
Jrue Holiday was a fantastic addition for the Celtics when they acquired him from the Blazers two years ago. He was a key part of Boston's championship run in 2024 and will forever be a legend in Beantown. But it's not a surprise that the C's decided to move on from the veteran, and to get Simons — a legitamately good scorer — is about as good as fans could ask for in return.
I'm not sure how Joe Mazzulla will incorportate Simons into the C's lineup, but it would make sense to put him at the starting shooting guard spot, and have him and Derrick White both basically act as combo guards. Simons can handle the ball well, but passing isn't the strongest part of his game; he's turned into a capable passer the past two years, but not what I'd call an "advanced" facilitator. Hence, it makes sense in theory for he and White to essentially split ball handling duties in the backcourt, while Payton Pritchard stays in his sixth man role.
And for the Blazers (my Blazers, for the record) this doesn't look great on the surface, but... I understand it. Simons is on an expiring deal, and this, to me, signals that the leaguewide perception of Simons isn't as high as Blazers fans perception of him. General manager Joe Cronin likely knew that he had to move Simons eventually, —so to get a capable veteran for a team that played like a playoff contender the second half of last year is a fine return, no matter what hot take artists will try to tell you.
This move also might free up minutes for Scoot Henderson and Shaedon Sharpe, who Portland believes to be the backcourt of the future. Whether I believe that is still up in the air (I really want to believe it, for the record) but the logjam at guard made it tough to really determine what Portland has in Scoot and Shae. If Holiday sticks around in Portland, he'll certainly get minutes, but won't be as much a focal point in Chauncey Billups' offense as Simons was, clearing the way for a more fair evaluation for the other young guys.
This is a fantastic, fantastic move for Boston, and an unexciting — but fine, and perhaps necessary — one for Portland.