For two years now, the question in Portland hasn’t been if Scoot Henderson will take the keys to the franchise, but when.
Back in 2023, fans were eager to fast-forward the Scoot Era the moment he became Damian Lillard’s replacement. From Day 1, Scoot had the swag, the burst, the highlight tape, and the confidence to shine. But he also had the weight of expectations put on his shoulders, despite everyone knowing the rebuild was officially in its first stage.
Now, two seasons in, the “when” has shifted back to “if” for some, who still hope he has face-of-the-franchise potential.
Scoot’s rookie year was rocky. His second season? It was better, but inconsistent. The flashes were there with elite speed in the open floor, glimpses of a pull-up game, and a growing feel for pace. But the full package never came together.
Now, in a summer full of moves, Portland has presented Scoot with the ultimate opportunity despite introducing a new set of challenges for the 21-year-old.
Anfernee Simons is gone. Shipped off to Boston, the team’s highest-scoring, highest-usage guard no longer stands between Scoot and full-time offensive responsibility. Combine that with Deandre Ayton’s 18.9 shot attempts per game being released, and that feels like a potential game-changer.
Of course, the Blazers flipped the narrative right back by bringing in two high-usage veterans, Jrue Holiday and Damian Lillard.
Yes, that Damian Lillard.
In a move nobody saw coming, Dame returns on a three-year deal, not to be the face of the future, but to be a stabilizing presence both during and after his recovery. Add in Holiday, a two-time champion floor general, who Blazers fans remember for torturing Dame and CJ McCollum during the 2018 playoffs, and Scoot’s situation remains complicated.
That’s where the “ultimate challenge” comes in.
On paper, it looks like Scoot just got buried behind two better point guards. And maybe, in stretches, he will be.
Holiday, who also has three years remaining on his deal, is still one of the best defenders in the league and a calming presence to organize a team. Lillard remains one of the most dangerous shooters alive. When healthy, both command more than respect; they command the ball, which is something Scoot needs in his own hands to be effective.
Of course, there’s a flip side. Scoot now has the opportunity to learn from two of the best in the business. Portland may not be handing Scoot the keys, but they’re surrounding him with tools to help him eventually earn them.
When it comes to Holiday, he plays with a pace and discipline that Scoot can lack. Lillard, on the other hand, has mastered the art of manipulation, controlling defenders, bending coverages, and using his gravity to create for others.
Between Lillard and Holiday, there may not be a better duo to help a young guard learn how to play smart, not just fast. And the development doesn’t have to be linear. Scoot can share the floor with Jrue this season, and then Dame the next, whether Holiday is around or traded. Scoot can learn to play off the ball, find rhythm as a secondary attacker, and hopefully, eventually pressure defenses from the corners as a catch-and-shoot threat.
It won’t be simple, of course. The Blazers are more than just Holiday and Lillard. The team expects big things from Shaedon Sharpe this season. Deni Avdija can take another leap, too, especially as a secondary playmaker. And Portland’s X-factor might just be Yang Hansen, the 7’1” center already drawing buzz as a perimeter-capable creator.
That’s a lot of cooks in the offensive kitchen. But maybe that’s exactly what Scoot needs—a little friction going into his third year.
Scoot has always been at his best when challenged. His G League years weren’t about comfort, and neither were his first two NBA seasons. That’s part of what makes him such an intriguing bet. The resilience, the willingness to grind, the flashes of growth between setbacks—they’re all there.
This new roster? It demands that he evolve. And quickly. But that could be a good thing.
The truth is, Scoot’s window isn’t closing, but, realistically, it is shifting. This season might not be about taking over but instead transforming. Improving decision-making, tightening the handle, and learning how to command a game without dominating the ball will be important.
The role won’t be handed to him, but with both Lillard and Holiday at age 35, it’s there for the taking.
If Scoot rises to it—if he leans into the mentorship, absorbs the lessons, and is able to better control pace—he’ll come out of this season more ready than ever to lead. Maybe not by force, but by proof.
Because the best leaders? They don’t ask for the keys. They earn them.
That’s exactly what Scoot can do under the leadership of two stars nearing their final chapters.
Be the first to comment