Missing out on the playoffs has recently been the norm for the Portland Trail Blazers, but it's still not something their franchise is accustomed to overall. The Blazers have made the playoffs 37 out of 53 times in history, including 21 consecutive appearances from 1983-2003.
Given the franchise's consistent regular season success, it's easy to see why the front office and fans alike are eager to get back to the playoffs. General manager Joe Cronin said that making the playoffs next season is a reasonable expectation, calling it "definitely a goal of ours."
That would have been outlandish to say at the start of the season, but the Blazers surprisingly increased their win total by 15 while their young core took significant strides. Despite their progress, the odds will be stacked against Portland to make the playoffs in the Western Conference next season. That is, barring a blockbuster trade -- which they should hold off on.
It's great to have playoff aspirations, just as long as the short-term goal of making the postseason doesn't interfere with building a sustainable, championship-caliber team. Given where they are in their rebuild and, more significantly, their cap space, Portland would be better off making a more aggresive move the following summer.
Blazers must position themselves for the 2026 offseason
Portland has just $76.4 million on the books for the 2026-27 season, nearly $100 million less than next year. Fortunately, Deni Avdija is on a frontloaded contract and will be owed just $13.1 million that season, making him arguably the best contract in the association. They will also have Scoot Henderson ($13.6 million), Donovan Clingan ($7.5 million), Kris Murray ($5.3 million), and Toumani Camara ($2.4 million) still on rookie deals.
That's almost their entire young core that contributed to their end-of-season push for a play-in spot this season, giving Portland yet another reason why they need to trade away their veterans this summer -- the most important of which is Jerami Grant.
Grant is the only one who is on a questionable long-term deal that extends beyond next season, owed over $32 million annually over the next three seasons (assuming he picks up his player option). The Blazers need to move him by almost any means necessary, even if it means having to attach some draft capital along with the deal, as he's quickly become a negative asset to keep around. If they can find a way to do that, they'll have just $42.2 million locked up in 2026-27, providing them with a golden opportunity to land a star in free agency at that point.
Portland isn't a huge market or a popular free agency destination, but they could make a compelling case with their substantial cap space and a pitch that includes the opportunity to join a competitive young core that continues to trend in the right direction. This team is perfectly constructed to seamlessly add a star into the mix, as they already have solid role players in place, such as Camara and Clingan, who can impact winning without needing the ball.
That 2026 offseason should be the Blazers' top priority and at the forefront of each decision they make this summer. Portland has eight players eligible for an extension this summer, most notably Camara and Sharpe.
As of July 20, Camara could sign a four-year, $89.2 million extension. However, as ESPN's Bobby Marks notes, the Blazers would be wise to hold off on that extension until the following summer "to maximize their finances."
Sharpe is the more likely candidate to be extended this summer, especially given his emergence towards the end of the season. But the Blazers would be better off taking a similar approach to how the Philadelphia 76ers managed their cap with Tyrese Maxey. Maxey deserved an extension, but Philadelphia decided to hold off on it to have enough financial flexibility to add Paul George the following summer.
Extensions are just part of the equation, as Cronin also needs to consider the 2026 cap space in any potential trade. The Blazers are in an encouraging position with tremendous cap flexibility coming up, but they must preserve it with any move they make this summer.