The Portland Trail Blazers trading for 35-year-old guard Jrue Holiday is puzzling when you think about it from a timeline standpoint. They sacrificed future draft capital and financial flexibility in a win-now move when the goal is nothing more than simply making the playoffs. That's typically the type of approach that results in long-term purgatory, something Portland, unfortunately, knows all too well during the Damian Lillard era.
Why wouldn't they learn from that mistake? The answer involves Portland's front office dynamics, something that is often overlooked when evaluating trades. Despite their recent extensions, general manager Joe Cronin and head coach Chauncey Billups need job security.
Job security is getting in the way of Blazers' long-term success
With the Blazers up for sale, who knows who will ultimately wind up being the new owners? The underlying factor behind this trade is that it will be much more challenging to convince the new ownership not to clean house if Portland misses the playoffs for a fifth straight year.
"I firmly believe that Cronin and Billups must win next season with a new owner on the horizon," The Oregonian's Aaron Fentress said on X. "Jrue Holiday is a win-now addition that could help this team reach the postseason. His contract is irrelevant because Cronin and Billups might not survive an ownership change if they experience their 5th consecutive losing season."
The fact that Holiday's massive contract -- owed $104.4 million over the next three years -- is being labeled "irrelevant" is the exact type of thing that should have Blazers fans concerned.
Irrelevant for Cronin? It clearly wasn't a dealbreaker. But that's not just something the Blazers can simply ignore. It's a Nico Harrison-type move in the sense that Cronin no longer seems to be worried about the ramifications four or five years down the line.
Could this wind up saving their jobs? It's hard to say how things would have played out either way. But it's ironic because this type of myopic thinking would have the opposite intended effect and would persuade us not to keep Cronin around.
The Blazers are now at risk of purgatory
Landing Holiday is a short-term upgrade and a better fit than Simons. But is it even enough to make the playoffs in a loaded Western Conference that somehow only continues to get better?
The Thunder will look to defend their crown and have all 15 players under contract for next season. The Lakers have a whole summer to surround Luka Doncic with complementary pieces. The second-seeded Rockets just landed a top 20 all-time player in Kevin Durant. We could continue because, well, every team in the West wants to be competitive outside of the Utah Jazz.
The Blazers should be patiently zigging while the rest of these teams are zagging. Instead, they find themselves in no man's land with teams like the Kings. Portland has more up-and-coming pieces than Sacramento, but are we sure Cronin is done?
Trading for Holiday doesn't guarantee a playoff spot. In fact, we'd still say they're more likely than not to miss the playoffs for the fifth consecutive season with their current roster. Will the Blazers continue trading valuable future assets to end this drought?
While having Holiday will be much more entertaining for fans who want their team to return to playoff relevancy, we can't help but wonder if this was too much of a brute force to fix that issue. One that could cause more problems down the road, given Holiday's age and contract. Not to mention any other potential moves Cronin has up his sleeve in an attempt to keep his job.
Unfortunately, these front office dynamics are a part of sports, so we don't necessarily fault him. But at the same time, fans have to wonder if Cronin no longer has Portland's best long-term interest in mind. Both things can be true, and Blazers fans should be worried if that is indeed the case.