General manager Joe Cronin has win-now aspirations for an up-and-coming Trail Blazers team that showed significant growth last season, saying that "it's winning time" in Portland. He also showed that through his actions by swapping Anfernee Simons for an aging (and declining) Jrue Holiday.
But the Blazers' rebuild isn't done -- they need to continue stressing patience. Attempting to compete for a playoff spot with win-now moves risks limiting their overall playoff ceiling. Portland still doesn't have that bona fide star to guide them through a deep playoff run, and they need to pump the brakes until they find that missing piece.
"I think the goal should be Lotto again. I want to be in the lottery again if I'm the Blazers," Kevin O'Connor said on The Kevin O'Connor Show. "I think their team has a lot of good talent -- a lot of players that could potentially be championship-caliber role players -- but I don't think they have the guy yet. I don't think they have the guy to lead a championship team yet. And that's in part because Scoot Henderson is looking like a really good player potentially, but not an All-Star type of player."
Blazers can find missing star in loaded 2026 class
The Blazers could trade for a star, but they must be very selective about who that player is. It's oftentimes a catch-22 because the only stars worth sacrificing valuable assets for are the ones teams aren't willing to give away unless it's a significant overpay. Portland is projected to have cap space in the 2026 offseason to potentially add a big-name free agent, but that shouldn't be counted on, as Portland isn't popular free agency destination.
The best bet for a rebuilding, small-market team to land that star is via the draft. One of Portland's strengths is in its scouting department and assistant general manager Mike Schmitz, a former ESPN draft analyst. They need to capitalize on that strength by increasing their likelihood of landing a top pick and finding that 1a star.
"This year's draft class in 2026 likely has that guy AJ Dybantsa at BYU, Darryn Peterson - point guard at Kansas, or [Cameron] Boozer going to Duke. There are some guys that could be the star of a championship team," KOC added. "So, to me, I think that's going to be the No. 1 priority for the Blazers. Be competitive, but don't make the play-in. I want to be in the lottery."
The 2026 unprotected first-round pick the Pelicans sent the Hawks for Derik Queen would have solved Portland's dilemma -- they could have made that playoff push and gained valuable experience for their young core while simultaneously landing a top ten pick. But now that the Blazers are forced to pick one or the other, positioning themselves for another lottery pick is the right decision.
Cronin may feel more pressure to win now, considering the Blazers have an active four-year playoff drought with new owner Tom Dundon set to take over in 2026. But hopefully, that doesn't cause him to ignore Portland's dire need to land a star in the draft.