General manager Joe Cronin has high expectations for the Portland Trail Blazers heading into the 2025-26 season. Recently, he outright said that "it's winning time" in Portland, but those intentions have been clear dating back to last year.
The Blazers were among the few teams not to make a trade at February's deadline. Part of that can be attributed to Cronin not wanting to ruin any momentum. Instead of shutting things down as they have in past years, Portland was striving to make a play-in spot in a competitive Western Conference. They ultimately fell short of that goal, finishing with a 36-46 record. But last season's 15-win improvement proved that their young core is too talented to tank, as Portland's youth was primarily responsible for their midseason turnaround in the first place.
The Jrue Holiday conundrum
Now, Cronin and the Blazers are looking to build off that momentum, with aspirations of achieving, at worst, a play-in spot this time around. That's one of the key reasons they decided to swap Anfernee Simons for a 35-year-old Jrue Holiday.
The idea behind bringing in Holiday was that he'd help Portland achieve both its short- and long-term goals with his championship experience and leadership, which will help unlock Portland's young core. However, adding Holiday into an already complicated Blazers roster puts them at a crossroads. They will be forced to decide whether to prioritize the present or the future, particularly when it comes to their starting lineup.
The Blazers' frontcourt should already be decided, with Toumani Camara, Deni Avdija, and Donovan Clingan. Those two final starting spots will likely come down to who earns it between now and the start of the 2025-26 regular season. The four candidates include Holiday, Scoot Henderson, Shaedon Sharpe, and Jerami Grant. Even with Holiday's declining play (11.1 points and 3.9 assists last season), he's still the best player of this group.
But the critical question the Blazers must ask themselves is this: Is Holiday really a positive impact on the development of Henderson and Sharpe if he's the very reason they aren't starting?
A starting five of Henderson, Sharpe, Camara, Avdija, and Clingan would be in Portland's best long-term interest, which should be the priority. Making the play-in isn't as important as the process of trying to achieve that goal. In other words, that's fine for Cronin to strive towards, but only as long as it's not coming at the expense of Portland's future. With Holiday getting in the way of Portland's young backcourt and his $104 million contract on the books, it literally is.