Holiday's 1-for-3 trade evaluation: Celtics gain multiple assets rated B, while the Blazers receive a confusing C

On June 24, Beijing time, the Celtics and the Blazers completed a 1-for-3 trade, sending 35-year-old guard Holiday in exchange for 26-year-old guard Anfernee Simons and two future second-round picks.

The Celtics initially acquired Holiday from the Blazers before the 2023-24 season, making him the final piece in their championship pursuit. At that time, Holiday was part of a three-team trade—previously, the Blazers had sent Lillard to the Bucks and then traded Holiday to the Celtics in exchange for Brogdon, Robert Williams III, and two first-round picks.

What does this trade back to Portland mean for Holiday and the Blazers? How will Simons fit into the Celtics' plans? Who is the biggest winner? The Athletic rated this trade—

The Celtics received Simons and two second-round picks, rated B

The Celtics' goal in trading Holiday seems to be to acquire immediate-impact players, and they might have even secured a first-round pick if another team was interested. Although they did not obtain a first-round pick, Simons has the potential to assist the Celtics, who may face turmoil next season. Currently, it's speculated that Tatum might miss the entire 2025-26 season, or at least a significant portion of it, and players usually struggle to regain their form after recovering from an Achilles tear. Despite losing Holiday, the Celtics have effectively temporarily lost Tatum as well.

Simons can help fill some of the scoring void. He is a highly talented scorer and an underrated playmaker. While he is not a pure point guard, he handles the ball well, passes effectively, and can create space. With a career three-point shooting percentage of 38.1%, over half of his attempts last season came from beyond the arc, which aligns perfectly with the Celtics' offensive style of relying on three-point shooting to break down defenses. Simons shoots without hesitation.

The question is whether he can adapt to the defensive system. Even last season, when he struggled with injuries and a decline in performance, Holiday was a member of the All-Defensive Team and provided far superior defense compared to Simons. This will be a challenge for Mazzulla: to have Simons move according to the Celtics' defensive expectations while maintaining overall defensive intensity. Although the Celtics are cutting costs, it does not mean they will become weaker. They will still compete for a playoff spot, but they are no longer the 60-win powerhouse.

With this trade, the Celtics saved $40 million in luxury tax, and their final salary should be below the second luxury tax threshold, although they still need to address the pending free agency issues of Horford and Kornet. Simons has one year left on his contract, with a salary of $27.7 million for the 2025-26 season, after which he will become a free agent.

The Blazers reacquiring Holiday is rated C

The motivation behind this trade for the Blazers is puzzling. They might believe that Simons has no future with them, or perhaps he does not wish to re-sign there. Alternatively, the Blazers may feel that he does not align with the defensive philosophy they occasionally showcased last season, or they might want to free up more playing time for Shaedon Sharpe.

The keys may now be handed completely to Henderson, who performed excellently in the latter half of last season. Regardless, sending out Simons and two second-round picks in exchange for the "privilege" of paying 35-year-old Holiday $32.4 million for the 2025-26 season and $34.8 million next season, while hoping he does not exercise his $37.2 million player option in 2027 when he's 37, is perplexing.

I would understand this trade better if the Blazers received draft picks in return. Instead, they are taking on more salary for a player who seemed to be declining last season. If Holiday can bounce back, this could be a fantastic acquisition. He can teach Henderson a lot and is a suitable partner for him. When healthy, he can still shoot and lock down scorers. However, he has missed 63 games over the past four seasons, including 20 last season.

Perhaps the Blazers believe Holiday will regain his health and perform well on the court before they trade him again? The last trade was indeed successful, but at that time, the contract, age, and health status were more attractive to potential trading partners. Losing Simons may not be a bad thing; he is a talented player but not a core piece that must be retained long-term. We just aren't sure if this version of Holiday is worth the price.