To an extent, the Trail Blazers already entered the offseason straddling two timelines with Anfernee Simons and Deandre Ayton, but both were young enough to be considered part of their young core had Portland decided to commit to them long-term.
Time will tell whether moving on from both players was in their best interest. Unsurprisingly, they did, but the idea was to move on from them to clear the path for recent top ten picks Scoot Henderson, Shaedon Sharpe, and Donovan Clingan. The Blazers had other plans, such as bringing in Yang Hansen, Jrue Holiday, and now Damian Lillard.
As a result, the gap between Portland's two timelines has widened. That has led ESPN's Tim Bontemps to question the Blazers' direction after Joe Cronin's roster decisions.
"I just don't really get what Portland is trying to do in general. They have this roster that doesn't really make a lot of sense," Bontemps said. "They've now drafted centers in back-to-back years. They draft Yang Hansen 16th overall after drafting Donovan Clingan the year before. Can they actually play together? I don't know. They have Scoot Henderson and Shaedon Sharpe that they drafted high in the lottery the last couple of years, and they haven't been starting."
Blazers must pick a direction and build toward it
Bontemps also touches on Deni Avdija's team-friendly deal of $39.4 million over the next three years. While it's great that Deni has arguably the best contract in the association, it's also not as helpful for Portland's rebuild if they can't capitalize during that contract window. As Bontemps notes, the Blazers likely won't be ready to contend until Avdija's contract is up and he's set for a massive new deal.
Additionally, any advantage Portland has with Avdija's contract and their multiple rookie-scale deals is essentially negated by having Jerami Grant and Holiday on the books.
Keeping veterans like Grant, Robert Williams III, and Matisse Thybulle around and adding aging stars like Holiday and Lillard would make perfect sense for a team like the Houston Rockets, who have a young core that already finished second in the West and could be a piece away from winning a title (hence their trade for Kevin Durant).
But for a Blazers team that exceeded expectations by winning just 36 games, and has a projected win total of just 32.5 for the 2025-26 season, we unfortunately have to agree with Bontemps on their lack of direction.
Portland has an exciting young core, but it isn't ready to contend and nowhere near Houston's star power. They should be organically leaning into their rebuild, with players like Henderson and Sharpe being the key determining factor in whether they reach the playoffs. That way, if Portland makes the postseason, they know their young core is ready to add veteran pieces to it. If not, they continue adding valuable draft prospects to that young core until it reaches that point.
Brute forcing a playoff appearance with aging stars is a shortsighted move that winds teams up in purgatory.