Damian Lillard’s return to Trail Blazers puts Scoot Henderson squarely on the clock in Portland

The news that Damian Lillard is returning to the Portland Trail Blazers tells us a lot of things. One, Lillard is more interested in returning home to be near his family and rejoining the organization that drafted and developed him into a future Hall of Famer than he is in chasing a championship, which he is all but sure to end his career without if this is indeed his last stop. 

Two, the Blazers are bringing Lillard back as much for his value as a mentor as his actual basketball ability, which will still be significant but likely not up to his superstar standard when he returns to the court more than a year from now. 

Which brings us to number three. 

Scoot Henderson is on the clock. 

Indeed, the Blazers have a lot of young players who can and hopefully will benefit from the tutelage of a veteran like Lillard, but Henderson is the guy who was supposed to be Lillard’s direct successor. That’s the reason why Lillard was traded in the first place. To clear a path for Henderson to take over as the next franchise player. But some halfway decent stretches notwithstanding, he has failed to take meaningful steps down that path through his first two seasons. 

How Damian Lillard just won the offseason by returning to the Trail Blazers

James Herbert

If Henderson doesn’t make the proverbial leap in Year 3, Lillard will likely be back as Portland’s starting point guard in 2026-27, and from there, who knows how Henderson’s career will shake out? Once you have the backup tag, it’s hard to shake. Certainly, nobody would be turning their offense over to him if he were given three years to earn that responsibility in Portland and failed to deliver. Right now, he has the look of a journeyman point guard who will end up coming off the bench for a lot of teams over the course of an ultimately disappointing career. 

But this year, he has a golden opportunity to flip that script, to tap into the potential that had so many of us downright drooling over him mere minutes into his first summer league game after Portland got him at No. 3 overall behind Victor Wembanyama and Brandon Miller in 2023. 

Simmons wasn’t alone here. Just about everyone loved Scoot, including, obviously and most importantly, Joe Cronin, who jettisoned probably the best player in franchise history to hand a teenager the keys. Cronin’s move to bring Lillard back isn’t necessarily an indication that the Henderson trial period is over, but ironically, Lillard now represents Scoot’s potential successor. This is a crazy league. 

Now, the Blazers don’t want it to play out that way. In a perfect world, Henderson, who will likely start out in a bench role behind Jrue Holiday and Shaedon Sharpe (who, incidentally, is also sort of on the clock as he and Scoot were supposed to be the future backcourt) will parlay the intangible value of veteran wisdom with the tangible threat of Lillard eventually replacing him into a breakout season. 

We know that talent isn’t an issue. He’s an elite athlete among elite athletes. In theory, there shouldn’t be many guys who can stay in front of him, or, even if they do, deal with his physicality. Consistency and continued progression toward at least league-average shooting are the keys. He can still get there. He’s only 21. 

And again, Portland is still invested in it happening. From a pure basketball standpoint, the trade for Holiday was a strange one in that Portland signed up to pay north of $100 million over the next three years for a 35-year-old player on the decline. But as a mentor, Holiday made perfect sense, at least before Lillard became available, for Scoot. 

More importantly, Anfernee Simons, Portland’s starting point guard last year, was sent to Boston in the Holiday deal. At this point, Simons is a significantly better player than Henderson. You don’t make that move unless you are committed to clearing enough minutes and touches to give Henderson an honest opportunity to finally fulfill, or at least seriously begin to fulfill, his full promise. 

If he can’t do it now, with Simons out of his way and Lillard and Holiday whispering wisdom into his ear, some hard questions are going to have to be answered with Henderson up for a rookie extension next summer and eligible for restricted free agency the next. 

The Blazers would love for Henderson to eliminate the need to even ask the question of whether Henderson fits into their future plans, or even better, who their starting point guard will be in 2026-27. If this time next year the Blazers’ biggest problem is whether Lillard will accept a bench role behind Henderson, they’ll be grinning from ear to ear. But they aren’t going to hand Henderson anything. They’ve put the ball in his hands. Now it’s up to Henderson to do something real with it.