Reactions are pouring in to the surprising trade that sent Anfernee Simons and two second round picks from the Portland Trail Blazers to the Boston Celtics for Jrue Holiday. The move is the talk of the NBA, a rarity for Portland.
Here’s a rundown of some of the expert reactions to the swap.
Zach Harper, The Athletic
Celtics: B
Blazers: C
Harper feels that Simons has the opportunity to help the Celtics replace some scoring, especially with Tatum missing most or all of the 2025-26 season. The question is whether he will fit in on the defensive end.
As for his thoughts on the Blazers:
I … do not understand this trade for the Blazers. It’s possible they just didn’t see a future with Simons. Maybe he didn’t want to sign an extension there. Perhaps they didn’t think he fit into a defensive mentality they seemed to occasionally form last season. Maybe they wanted to open up more minutes for Shaedon Sharpe. The keys could now be fully handed over to Scoot Henderson, who played well in the second half of last season. Regardless, sending out Simons and two second-round picks so you have the privilege of paying a 35-year-old Holiday $32.4 million for the 2025-26 season, $34.8 million the following season and then praying his 37-year-old self doesn’t pick up a $37.2 million player option in 2027 confounds me.
Sam Quinn, CBS Sports
Celtics: A
Blazers: C-
The worst-case outcome for Boston as Quinn sees it is that they got off of Holiday’s contract, saved some salary this season, and even snatched up a few picks. Not bad, even if they let Simons walk after this season. The best case is that Simons the “gunner” fits in and delivers on the offensive end, and he might have room to grow still.
As for the Blazers, Quinn goes through every possible positive angle for Portland. It’s a good effort, but he’s not really buying his own arguments.
So the actual upside here seems pretty limited. The downside, though? That’s much more severe. First of all, the Blazers had pathways to around $50 million in 2026 cap space. That’s now gone. Holiday occupies most of that space. Second, Portland already owed too much money to one declining, veteran wing in Jerami Grant. Now, they have another in Holiday, and together, they present some meaningful financial issues moving forward.
Morten Stig Jensen, Yahoo Sports
Celtics: A
Blazers: C
Stig Jensen is in near disbelief that Boston was able to extract themselves out of a difficult situation with the Holiday contract. Not only that, they got assets to boot.
For the Blazers:
In totality, while you can see the vision of Portland if you squint, it remains odd that the Blazers went this hard after a 35-year-old with over $104 million left on his deal, knowing how much the Celtics needed to shed salary.
Kevin Pelton, ESPN
Celtics: B-
Blazers: C-
Pelton sees Simons giving Boston a reliable offensive asset while being a potential piece for matching salary in a trade down the road. Perhaps there was a better trade out there for Boston, but this trade helps them with their goals.
From the Blazers perspective Pelton runs through some possible positive outcomes, but the playoffs are still less than a 50/50 proposition in his view. His bottom line:
The hard reality of NBA rebuilding is the easiest way to short-circuit things is to push in too early, capping the group’s potential in favor of modest success that eventually feels hollow. Trading Holiday alone won’t do that for Portland, but it’s not an promising indicator of the team’s priorities.
Andy Bailey, Bleacher Report
Celtics: A
Blazers: B
Lower salary, Simons expiring contract, the possibility Simons could work out, and the draft capital received all get cited by Bailey as reasons for his A grade for Boston.
Bailey’s thoughts for the Blazers are mostly positive too. He likes Holiday’s fit, having demonstrated he can share the floor without having the ball, hit open shots, and play some defense. It’s not all rosy though:
Well, giving up draft assets (multiple) for a 35-year-old guard who just saw his scoring average dip to 11.1 in 2024-25 (and 9.5 in the 2025 playoffs), even if they’re second-rounders, isn’t ideal.
And perhaps more importantly, Holiday’s contract has the potential to age poorly. There are three seasons left. He’ll be 38 when it ends (assuming he picks up the $37.2 million option for 2027-28). And in the West, there’s no guarantee Portland even makes the playoffs during the life of Holiday’s deal.
Still, Bailey feels the positives outweigh the negatives enough for the Blazers to earn their “B”.
As an addendum, John Hollinger of The Athletic didn’t give grades, but had this to say about the move for Portland [subscription required]:
Let’s wait and see what else the Blazers cook up this offseason; maybe they can wave a magic wand and turn [center Deandre] Ayton into a point guard and a shooter. At this moment, however, I am flabbergasted that they sent out draft capital to turn Simons into Holiday. Even if you think Holiday is the better short-term fit, the nine-year age difference on a team that is not exactly contention-ready is a major minus for the out years, and they got nothing else back for their trouble. I don’t get it.