The Portland Trail Blazers brought in veteran Jrue Holiday to provide valuable mentorship to help unlock up-and-coming backcourt pieces Scoot Henderson and Shaedon Sharpe. From that standpoint, Portland couldn't have picked a better player to bring in. Holiday is a proven winner at both the Olympic and NBA levels. He's a star guard who has bought into a team-first mentality, which contributed to those championships on his resume.
Between Chauncey Billups, Damian Lillard, and Holiday, the Blazers have built an elite infrastructure to support growth. However, the issue with Holiday in particular is that he's going to be cutting into the on-court production of these players.
Jrue Holiday is blocking the development of his own students
Portland has three players who should be considered locks to start: Deni Avdija, Toumani Camara, and Donovan Clingan. Assuming that is the case, it leaves just two spots left between four players: Holiday, Henderson, Sharpe, and Jerami Grant. That forces Billups to decide whether to prioritize youth or winning.
In a perfect world, the Blazers want to win because of their youth. That's just not realistic, given how behind they already are in the landscape of the Western Conference.
If Portland wants to end a four-year playoff drought, or even earn a play-in spot for that matter, they are going to have an extremely slim margin of error. That goes out the window when considering the growing pains that they'll inevitably have to endure if they prioritize the likes of Henderson and Sharpe. Both are promising guards who have shown flashes of their respective star ceilings, but neither has been able to put it all together on a consistent basis yet.
Portland's best bet to eventually catch up in the West is for these young guards to take the next step. In theory, Holiday will help achieve that. But Portland already has mentorship in place between Billups and Lillard, with the latter likely sidelined for the entire 2025-26 season. That makes Holiday's purpose on this team redundant, diminishing the value of keeping him around.
Holiday is brought in to be a mentor, but is going to take away minutes and touches, and potentially a starting role from the very players he was brought in to help. Considering the diminished value of his mentorship, Portland's starting lineup dilemma, and his massive contract, the cons of keeping him outweigh the pros. The Blazers were wise to trade Anfernee Simons and get assets before having to deal with his looming expiring contract. However, by swapping Simons for Holiday, Portland merely traded one crowded backcourt situation for another, more expensive one.