For better or worse, Portland Trail Blazers general manager Joe Cronin surprised the NBA world on multiple occasions this past offseason. Nobody expected Portland to be in the running for a 35-year-old Jrue Holiday, and their first-round selection of Yang Hansen was even more surprising.
These were puzzling moves at the time, and now, 36 games into the season, it's no easier to wrap our heads around the decisions.
The most confusing aspect is the conflicting timelines. Acquiring an aging and overpaid Holiday is a move that a contending team makes when they think they are a piece away. Drafting a boom-or-bust project in Hansen is the move a rebuilding team makes when it has no win-now aspirations and can afford to be patient with his development.
Despite the trade for Holiday, Cronin maintained that the Blazers' rebuilding approach is leaning towards the latter timeline surrounding Hansen. They are playing the long game, with Holiday seemingly being an exception to the rule. But why was that the case?
Blazers' Jrue Holiday trade turning out to be a shortsighted move
Early on, it was apparent that Holiday was an upgrade over Anfernee Simons on both sides of the ball. His athletic decline was also evident, but Holiday is the type of player who can prolong his career with his basketball IQ, playmaking, and unselfish play, among other winning intangibles.
But unfortunately, the Blazers were too reliant on a 35-year-old with an injury history. Holiday went down with a calf strain on Nov. 14. We're now in 2026, and the veteran guard still has no timeline to return. Since then, Portland has gone 10-14, roughly a nine percent drop in win rate. Their lack of backcourt playmaking has been on full display -- something they've managed to overcome in their wins and something that has directly caused several of their losses.
Deni Avdija and the Blazers deserve a ton of credit for staying afloat as they still sit 9th in the Western Conference. The Western isn't as deep as advertised, giving Portland a realistic shot at a play-in spot. Holiday could even contribute to that run once he finally does return. But then again, what is the end goal here?
This was a shortsighted move that could become a significant roadblock in the Blazers' rebuild once their young core is finally ready to contend. They already had a negative asset in Jerami Grant to deal with, and will now owe two veterans who don't fit their timeline over $100 million the next three seasons.
Holiday has been great for Portland when healthy, but he's also not the needle-mover to elevate them to contention status -- not when the rest of their young core isn't ready.
Given his age, lengthy contract, and injury-proneness, this offseason decision was just questionable timing. It leads us to wonder whether the move was an attempt to save Cronin's job, with Tom Dundon set to take over as owner while the Blazers are in the midst of a four-year playoff drought.
Whatever the motivation, hopefully it doesn't turn out to be the shortsighted move that derails the Blazers' rebuild. They still have an up-and-coming young core that has stepped up during Holiday's extended absence.