The Portland Trail Blazers' messy roster got even more complicated after this surprising offseason with the additions of Damian Lillard, Jrue Holiday, Yang Hansen, and Blake Wesley. Portland was already juggling two timelines as a rebuilding team with multiple veterans on the roster, some of whom were interfering with the development of their young core. The gap between those timelines has become even wider as the Blazers moved on from their bridges that could fit either one, including 26-year-old Anfernee Simons and 27-year-old Deandre Ayton.
It's not an ideal situation, but it's also a self-created problem.
Veteran additions complicate Blazers' young core
The Blazers are a 36-win team that exceeded expectations playing in a dominant Western Conference. They should be incredibly patient, prioritizing the development of recent first-round picks Shaedon Sharpe, Scoot Henderson, Donovan Clingan, and Yang Hansen above all this upcoming season. But instead of zigging (tanking) while the rest of the West is zagging (winning), Portland is attempting to keep up. The most obvious example of this was trading Simons for 35-year-old Holiday, but Cronin has repeatedly gone on record saying that Portland also wants to win now.
Cronin's impatient moves complicate things for the Blazers roster, particularly when it comes to the starting lineup. Portland's frontcourt is solidified with their building blocks of Deni Avdija, Toumani Camara, and Donovan Clingan (until Hansen proves otherwise). With the final two starting spots, head coach Chauncey Billups must decide what direction to take Portland's rebuild. Does he lean into development with Henderson and Sharpe, or prefer experience with Holiday and Jerami Grant?
That answer remains to be seen, but if it represents where the Blazers' roster currently is, it may be a combination of the two timelines: Henderson and Holiday.
Sharpe could be the odd man out at the worst possible time
Despite his declining play (11.1 points and 3.9 assists), Holiday's two-way impact and championship experience make him Portland's best bet to help them win games out of those remaining options. It's possible Billups even elects to start Holiday and Grant, which would likely infuriate every Blazers fan out there. But starting Holiday and Henderson together in the backcourt is a realistic option -- one that became much more viable after Holiday's recent comments during his media availability, in which he discussed his complementary fit alongside Henderson in particular.
Last year, it was Grant that made Sharpe the odd man out of Portland's starting five after Billups benched him midseason for his lack of defense. This time around, it could be another veteran taking Sharpe's spot in Holiday.
The Blazers are caught in this cycle where they want their young core to match their win-now approach, but they aren't prioritizing their development enough to make that realistic. And they keep pushing that threshold further with each veteran addition. That's the exact opposite approach Portland should have at this point in their rebuild, and it couldn't have come at a worse time.
The Blazers have until the start of the 2025-26 season to decide on Sharpe's extension as he enters the final year of his rookie-scale contract. If nothing materializes, Sharpe will become a restricted free agent next summer. And if Portland isn't making him a priority this season, they won't have as much clarity to help make what could be a franchise-altering decision.