In their one-for-one swap of Anfernee Simons for Jrue Holiday, the Portland Trail Blazers are adding a two-time NBA champion, two-time All-Star, and six-time All-Defensive Team member.
In theory, the addition of Holiday will help achieve their goal of making the playoffs as soon as the 2025-26 season. He's also going to be a valuable mentor for Scoot Henderson and the ideal fit for their defensive identity.
While this all remains to be true, there's one issue that makes this a questionable trade for the Blazers, and one general manager, Joe Cronin, could ultimately come to regret: Holiday simply isn't that good anymore.
Jrue Holiday's declining play makes Blazers' trade all the more puzzling
Last season with the Celtics, Holiday averaged just 11.1 points, 4.3 rebounds, 3.9 assists, and 1.1 steals per game on 44/35/91 shooting splits. He also recorded the third-lowest minutes average of his career at 30.6, with Sixth Man of the Year (and Oregonian) Payton Pritchard taking his minutes. Holiday is a 35-year-old guard who has dealt with injuries, with Portland ultimately revising their trade because of slight concerns surrounding his medicals.
The silver lining is that Scoot Henderson now has a golden opportunity to take over as a focal point of the offense in a pivotal third season.
Between Damian Lillard's expected gap year and Holiday requiring a lower usage rate than Anfernee Simons, Scoot is well-positioned to have a breakout season and showcase why he was a No. 3 overall pick not too long ago.
Surprisingly, the trade for Holiday was a steep investment in Henderson. But at the same time, we also can't help but wonder if Henderson would've been better off with Holiday out of the picture. Portland went from one backcourt logjam to another with this trade, and Henderson already has one of the best point guard mentors in the game with Chauncey Billups as his head coach.
Simply put, the cons of acquiring Holiday outweigh any pros. Factoring in his three-year, $104 million contract and where he's at in his career, Holiday is a player who only makes sense for a contending team desperate to add an additional piece to put them over the top. He's no longer talented enough to be the needle mover Portland still needs.
Given where the Blazers are in their rebuild, they would've been much better off trading Simons for draft capital and a salary filler instead of Holiday, especially now that Lillard is back home.