Trail Blazers general manager Joe Cronin has said it's a "reasonable expectation" for Portland to make the postseason in 2025-26. There's a wide gap between where Cronin thinks the Blazers are and where they actually stack up in the loaded Western Conference. And it's wrecking their rebuild.
Last season's end-of-season stretch, primarily led by their young core, was encouraging for the Blazers' future outlook. They have a legitimate foundation to build off of after a top ten defensive finish in 2025. But that doesn't mean that the playoffs are suddenly in reach and that Portland is a Jrue Holiday-Anfernee Simons swap away from that ambitious goal coming to fruition.
For instance, the Blazers have a projected win total of 32.5 on DraftKings, which is a far better indicator of what reality is for this young Portland team rather than an overly optimistic GM.
Joe Cronin is leading the Blazers to purgatory
As a result of the head-scratching trade for Holiday, the Blazers are now on the books for a declining 35-year-old guard who is owed $104 million over the next three years (accounting for a player option). Combine that with Jerami Grant's $102.6 million during that same stretch, and Portland suddenly has two of the worst contracts in the entire association.
This offseason, we've seen the new CBA's impact on teams and players alike. The Boston Celtics had to dump the salaries of Holiday and Kristaps Porzingis. Free agents are signing for team-friendly values because everyone is afraid of overextending their budget.
We've even seen the Blazers fail to make a free agency addition up to this point despite their $14.1 million MLE because they want to keep their books clean. That's understandable as Portland will have a lot of rookie-scale players due for extensions in the coming seasons. But why contradict that by taking on one of the worst contracts in all of basketball? And at that point, why not fucommit to making subsequent moves to help make the postseason more attainable? Or at the very least, keep a flawed but talented Deandre Ayton around for one more season?
Holiday has won championships in Milwaukee and Boston because he was the missing piece they needed for a ring. Meanwhile, Portland knows it can't contend out west, but Cronin hopes that an aging Holiday will push them back into the playoffs. That type of thought process derails teams' rebuilding trajectories and winds them up in purgatory.
The Blazers missed out on any potential draft capital they could have gotten for Simons elsewhere. And because of the upgrade from Simons to Holiday, they will now likely have a worse draft pick next summer. They also have yet to resolve their starting lineup issue surrounding Scoot Henderson and Shaedon Sharpe, as at least one will likely still come off the bench for a rebuilding team. Not to mention, there is a slight injury concern surrounding Holiday, with Portland having to revise the initial trade because of his medicals. This swap may be fun in the short term, but it has added more problems to Portland's plate.
The Blazers aren't ready to contend, and Cronin should've been more patient this summer.