Damian Lillard will be suiting up the next time the Portland Trail Blazers play basketball. That's an exciting thought, as it's felt like longer than three seasons since Portland has played without its franchise icon.
But this isn't the same team that Lillard left in 2023, evidenced by their recent playoff appearance without him. That's for the best, as it signals the Blazers will be bringing in Lillard as a bonus rather than relying so heavily on him to solve all their problems after such a brutal injury this late in his career.
However, it does complicate Portland's backcourt picture in the short term. The Blazers have two aging stars, Jrue Holiday and Damian Lillard, and two up-and-coming guards, Scoot Henderson and Shaedon Sharpe.
Blazers' two-timeline approach clouds Scoot Henderson's role
Portland is expected to receive plenty of trade interest in Holiday this summer. While they should at least listen to offers, Holiday's two-way skillset and versatility are the perfect fit alongside Lillard's offensive-minded game.
NBA insider Jake Fischer reported that team officials "believe the two veterans can function together nicely," noting their strong connection formed during the Tokyo Olympics. That said, he also adds that the Blazers could wind up trading Holiday to clear the path for Henderson.
"Isn't it conceivable that the Blazers would seek to create more backcourt opportunity for Henderson, whom they selected with the No. 3 overall pick just three years ago, by shipping out Holiday?"
This is the two-timeline dilemma that Portland's front office has brought upon itself.
Will the Blazers trade Jrue Holiday this summer?
Holiday mentioned at this exit interview that he'd like to stay and continue building in Portland. It remains to be seen if he gets his wish, and it could ultimately depend on how much value he has on the trade market.
I get the sense that Portland isn't actively shopping Holiday because they acquired him with the intention of keeping him this time around. But if they get an offer too good to pass up, I also don't see him as off-limits. That's the approach general manager Joe Cronin has taken throughout this entire rebuild: patient, but with a firm stance on trade value.
If it weren't for the postseason, I'd say to keep Holiday and Lillard and try to win now, given their closing windows. However, Henderson showed flashes of upside in that series against San Antonio that could justify an increased role.
Consistency remains an issue for their former No. 3 overall pick, but the Blazers haven't made it any easier for him. His role and minutes have fluctuated a lot, and Henderson would benefit from being made more of a priority.
Scoot Henderson's off-ball growth helps the backcourt logjam
Helping his case is that he's embraced a more off-ball role this season, making it easier to share the backcourt with Lillard.
"I've been playing off the ball more," Henderson said at his exit interview. "It'll be special to see how that pans out. Dame was one of my favorite players growing up. I used to play 2K and have 50 or 60 with him. It'll be special for Rip City to see that."
Henderson is quietly becoming an ideal role player for the Blazers. His career has taken a strange trajectory as he's developed into more of a 3-and-D piece than many expected, in part because of Holiday's veteran impact on defense.
The Holiday trade has gone perfectly to plan up until this point, but what is the plan now with Lillard back in the picture?
A crowded backcourt could prove to be a luxury for Portland, considering it was a major area of weakness for a team that struggled with shooting and playmaking. But the front office will have to balance Portland's short and long-term outlook this offseason, especially when it comes to Henderson's development. That could depend on how much they value Henderson in this rebuild. Is he truly a building block? The way this offseason shakes out should tell us where he stands.
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