By Last Word On Sports,Pocholo Magsino

Copyright yardbarker

As Simons has been traded to the Boston Celtics, Henderson will be Jrue Holiday‘s understudy next season. As Holiday’s a two-time NBA champion, two-time All-Star and six-time All-Defensive selection, this mentor-student dynamic should be beneficial for the 21-year-old. Of course, nine-time All-Star Damian Lillard can still provide some sort of tutelage despite the fact he’ll sit out the entirety of 2025-26. With that in mind, Henderson is still seen as Lillard’s successor and he wants to live up to expectations.

So far as the other backcourt spot, 6-foot-6 shooting guard Shaedon Sharpe practically has it locked up. As Billups demoted Sharpe to the second unit due to his defense last season, there’s always the chance that the Blazers will look elsewhere. Yet, their depth at the position suggests otherwise.

Sharpe’s primary backup will probably be former San Antonio Spurs guard Blake Wesley, who inked a one-year deal with the Blazers. At 22 years old, he still has loads of potential, but has a career scoring average of 4.3 points per game. Rayan Rupert is another project for Portland, but he had some promising flashes at Summer League, making him a breakout candidate. Two-way player Caleb Love could also make some noise, but he will probably play more in the G League with the Rip City Remix.

Portland’s Wing Depth is Impressive

Portland’s wing depth is impressive because it could help them compete on the same level as top teams. To reiterate, Camara and Avdija look to be the long-term starters in the forward slots. It could be argued that veteran Jerami Grant still deserves a spot. However, he’s been injury-prone in recent seasons and his play was particularly disheartening in 2025-26.