NBA trade grades: Does Anfernee Simons maintain Celtics’ status as East contenders?

We knew the collective bargaining agreement’s second-apron threshold loomed for the Boston Celtics, especially with the ruptured Achilles tendon Jayson Tatum suffered during the playoffs. As a result, we assumed the Celtics’ expensive roster from their 2024 championship run may be in line for an adjustment, with Jrue Holiday or Kristaps Porziņģis being prime trade candidates. Well, the Celtics wasted little time in finding a familiar trade partner involving Holiday.

Boston is trading the 35-year-old to the Portland Trail Blazers in exchange for 26-year-old guard Anfernee Simons and two future second-round picks, league sources confirmed to The Athletic. ESPN first reported the trade late Monday.

Boston originally acquired Holiday from Portland before the 2023-24 season as one of its missing pieces to get over the hump in pursuit of a championship. Holiday was part of the three-team deal that sent Damian Lillard to the Milwaukee Bucks before the Blazers flipped Holiday to Boston for Malcolm Brogdon, Robert Williams III and two first-round picks.

What does this trade back to Portland mean for Holiday and the Blazers? How does Simons fit into the Celtics’ plans? Who made out the best here? Let’s drop some grades on this deal:

Celtics acquire Simons and two second-round picks

It seemed like the Celtics’ goal for a deal involving Holiday was to get back a player who could help now and maybe a first-round draft pick, if a team was so inclined. The latter didn’t happen here, but Simons has the opportunity to help out a Celtics team facing some limbo next season. The assumption is that Tatum will likely miss the entire 2025-26 season. At the very least, he’ll miss the vast majority of it, and, even then, we don’t typically see players bounce right back once they return to the court from an Achilles tear. Although the Celtics are losing Holiday, they’ve already essentially lost Tatum in the interim.

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Simons can help replace some of the lost scoring. He’s a very talented scorer and an underrated playmaker. He’s not quite a lead guard, but he does a good job of taking care of the ball, moving it and stretching the floor. He’s a career 38.1 percent 3-point shooter, and over half of his shot attempts last season came from 3-point range. That fits in very well with the Celtics’ brand of offense that puts up a ton of 3-pointers and tries to bury your defense with them. Simons is not shy to let it fly.

The question will be whether he fits defensively. He’s not nearly the defender Holiday is, even compared to last season’s slowed-down version of the six-time All-Defense selection, who battled injuries. That will be Joe Mazzulla’s challenge: Getting Simons to move as necessary for Celtics guards to maintain teamwide intensity. Even though we are seeing the Celtics shed some salary, it doesn’t mean they’re going to be bad. They’ll still compete and be a playoff team. They just won’t look like a 60-win monster.

Boston should find itself below the second apron, although some work remains to be done with the pending free agencies of Al Horford and Luke Kornet. Simons has one year left on his deal, with $27.7 million owed in 2025-26, before he becomes a free agent.

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Grade: B

Blazers acquire Holiday (again)

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.

If the Blazers received a pick in the deal, I would better understand it. Instead, though, they took on more salary for a player who looked like he was breaking down last season. If Holiday can bounce back, it’s a great addition. He can teach Henderson a lot and pair nicely with him. He can still knock down shots and lock down scorers when he’s healthy. But he’s missed 63 games over the last four seasons, including 20 last season.

Maybe the Blazers believe Holiday will get healthy and look great on the floor before they can flip him again? It worked well last time, but the contract, age and health seemed much more attractive to potential trade partners in that instance. Losing Simons isn’t necessarily a bad thing. He’s a good player, but he’s not someone you have to keep forever. I just don’t know if this version of Holiday is the guy you give that up for.