The Portland Trail Blazers entered the 2025-26 season with aspirations of ending a four-year playoff drought. They were building off a strong finish to last season that propelled them into the play-in conversation, and all signs pointed towards that momentum carrying over.
Although the projected win total was similar to last year's 36-win season, on paper, this was supposed to be a much better team. For one, their up-and-coming roster would have an entire offseason to focus on internal improvement. But perhaps most significantly, Portland made a surprising win-now move to acquire a 35-year-old Jrue Holiday.
Blazers' Jrue Holiday trade is backfiring
It was a polarizing deal. The expectation was that Portland would trade Anfernee Simons to get ahead of his expiring contract and establish a defensive identity, but an aging star like Holiday never appeared to be in the cards.
He was coming off a down season in Boston in which he averaged 11.1 points, 4.3 rebounds, 3.9 assists, and 1.1 steals on 44/35/91 shooting splits. Those aren't bad numbers by any means, especially considering Holiday has always been a winning player who sacrifices his stats for the betterment of the team. Still, those numbers didn't scream $32.4 million player.
Holiday is the highest-paid player on Portland's roster this season, slightly ahead of Jerami Grant's $32 million. Portland can get away with it... for now, but it will eventually become a roadblock to retaining and upgrading its existing core. Deni Avdija, in particular, is someone whose contract will eventually have to be renegotiated and extended following his All-Star-level breakout.
In other words, it was a steep and unnecessary price to pay.
The Blazers didn't give up significant assets to land Holiday, as it turned out to be a simple swap. Instead, they paid for it in the form of his massive contract, one that gets more expensive as he continues to age. In the 2027-28 season, Portland is set to pay a 37-year-old Holiday $1 million for every year he's spent on Earth.
This all goes back to a bigger problem in their rebuild. With such a mix of youth and veterans, there's no clearly defined timeline for their contending window. They have veterans like Holiday and Grant who are overpaid but would make sense on a team looking to contend and desperate to upgrade their roster with limited assets. That doesn't apply to Portland.
Holiday was brilliant for this team when healthy, effectively taking on more of a playmaking role with Scoot Henderson still sidelined. But now Holiday is dealing with an injury of his own (calf strain) and hasn't seen the court since Nov. 14. That's an expensive 12 games played that Portland is paying him for.
It's the risk they took by adding an aging star with an injury history, and it's already backfired.