Blazers' core becomes crystal clear after Jrue Holiday trade

By trading away Anfernee Simons and two second-round picks to the Boston Celtics in exchange for Jrue Holiday, the Portland Trail Blazers and general manager Joe Cronin have made their stance on who they view as a part of Portland's core crystal clear. Moving forward, they are building around Shaedon Sharpe, Toumani Camara, Deni Avdija, and Donovan Clingan.

Where does Scoot Henderson now fit into Portland's plans?

Scoot Henderson still has time to join that core, but that will be put on hold after landing a clear-cut starter in Holiday. The trade is a half-baked vote of confidence in Scoot. Aaron Fentress of The Oregonian referred to the likelihood of Portland trading Simons as a toss-up, depending on their confidence in Henderson.

"Unless an ideal trade presents itself, and the Blazers are convinced Henderson can run the team, Simons will return as the starting point guard," wrote Fentress.

Given Holiday's age and contract, we wouldn't call this an ideal trade. And are the Blazers actually convinced Henderson can run the team? The idea of trading Simons was largely to clear the path for Henderson and give him the keys to the backcourt, which this trade didn't accomplish.

The silver lining for Henderson, however, is that this does give him a clear path to taking over that role in the near future. It takes the pressure off of him to immediately take over a role that Portland clearly didn't feel he was ready for, but still had optimism about his ability to one day get there.

The guard position takes the longest to adjust to in the NBA. Henderson will likely have three full seasons with two valuable mentors in Holiday and head coach Chauncey Billups (assuming Jrue picks up his $37.2 million player option in 2027-28). At that point, Henderson will just be entering his prime, giving him plenty of time to improve several aspects of his game, including defense, finishing, three-point shooting, and decision-making.

The trade for Holiday shows that the Blazers are doubling down on their defensive-minded identity under Billups. They were a top ten defense in 2025 and should continue to remain in that tier as everyone in their core outside of Sharpe is a lockdown defender. Holiday will not only bolster their previously lackluster backcourt defense, but he's also a better fit for their established core than Simons. He'll fit in seamlessly with their new-look offense built around Avdija as their point forward.

Most importantly, Holiday is a veteran who won't hinder the development of this core as someone who can impact winning without demanding the ball.

Some may question the fit of a rebuilding Blazers team adding a 35-year-old guard to their roster, but that's precisely why we like the deal relative to most. There was too much overlap with their existing roster. Now, there's a clear timeline and gap between Holiday and Henderson. With that comes much-needed clarity in terms of backcourt hierarchy and fit.