Damian Lillard is a member of the Portland Trail Blazers again. What a time to be alive. The star point guard’s return coincides with his 35th birthday and extensive rehab for an Achilles tear that will likely hold him out of the 2025-26 season. But those details don’t matter right now.
The Blazers have lured one of their greatest names back for the price of the Mid-Level Exception after securing a relative haul from his departure two years earlier.
Lillard won’t be his prime self and no one should
be expecting him to be. But on his return to the court, he should hopefully still be able to launch from the logo, attack the rim with above-average ferocity and pass adeptly to willing scorers. Honestly, if he’s 75 percent of the player he was, the Blazers should be popping champagne corks.
One of the biggest issues Lillard faced through his first stint with the franchise was his teammates. After LaMarcus Aldridge left, Lillard was stuck with CJ McCollum, Jusuf Nurkic and a list of names who didn't fit and were too gaudily paid to deliver a real contender.
Ironically, it was the trade that sent Lillard to the Milwaukee Bucks that gave current General Manager Joe Cronin the opportunity to build a versatile and sensical squad.
The first Lillard era never had genuine two-way wings who could relieve his offensive burden. The Blazers have that now. The first Lillard era never featured versatile size and length to help mask his own defensive deficiencies. The Blazers have that now. The first Lillard era rarely had depth that made sense. The Blazers have that now.
By the end of last season, many Blazers pundits, including this writer, remarked at how the Blazers had the perfect supporting cast but were without a genuine star or two. They still don’t have the star — Lillard’s age and physical limitations probably count him out of that category. But at least we get to see what it looks like with competent and complementary pieces around him.
As for the Blazers backcourt, I wrote earlier this month that Jrue Holiday should start over Scoot Henderson, alongside one of Shaedon Sharpe or Toumani Camara. That won’t change with Lillard unlikely to return to the court until October 2026.
But what does it mean for Henderson long term?
Pinning your future hopes on Lillard and Jrue Holiday, who both just turned 35, would be a little shortsighted, especially with Lillard not likely to play again until age 36.
But there’s an issue. Though still young, Henderson hasn’t reached the heights many had hoped for. The arrival of Holiday and Lillard are a testament to that. Henderson’s failed expectation has also likely been exacerbated by his draft position and the circumstances of him joining Portland just before Lillard’s initial departure.
This expectation may also make it difficult for him to remain in a lesser role on the Blazers moving forward. What I mean is that the Blazers might be better off trading Henderson to a team that still believes in his pre-draft prowess. A move far more shrewder than burying him on the bench.
Scoot Henderson
After jumping two spots at the 2023 NBA Draft Lottery, the still-rebuilding Blazers took the guy they believed was the best available player with the third pick. Unfortunately, that decision likely prompted Lillard’s departure given the position they both play.
But two years is an eternity in professional basketball. The now third-year guard has shown signs of an intriguing skillset but a severe lack of consistency.
Henderson clearly possesses natural passing ability, but the skillset is yet to deliver in reality. Sure, he hasn’t been surrounded by legitimate scorers but the fact that he finished in the 48th percentile in assist rate among point guards last season is telling.
He can shoot but concerns over his ability to navigate traffic, make smart decisions and take over games haven’t gone away. He’s an average defender who has the measurements, namely a 6’9 wingspan, to be decent but he’s also yet to show this consistently.
I’ve enjoyed his moments of production but I’m just not sold on his ability to do it night in, night out.
Three Point Guards?
Is there a world where Lillard, Holiday and Henderson can co-exist. The answer is obviously yes for the next 12 months. But come 2026-27 opening night, it gets complicated. Of the three, Holiday is the most competent off ball but I’m reluctant to have him share a backcourt with either Lillard and Henderson for too long, even with his defensive prowess.
For me, the Blazers probably need to keep two of the three. One starts and one comes off the bench. Why not start both? Because for the first time in years, the Blazers boast real size and talent at shooting guard, whether it’s Shaedon Sharpe or Toumani Camara. Why go back to two small guards again? We know this doesn’t work.
There’ll be periods where two of the three share the court but this team now has a defensive identity. It would behoove Chauncey Billups to lean into that identity.
Despite his defensive issues, when Lillard returns in 12 months, you’d have to expect the former Weber State star to be one of those two preferred point guards. And unless Holiday falls off a cliff this season, he’s the other.
For Henderson to usurp Holiday, the latter would have to start showing his age and/or the former would have to surprise us by taking a real leap in Lillard’s absence.
A leap for Henderson wouldn’t necessarily mean making February’s All-Star showcase. But it would signal improved decision making and finishing with a reduction in turnovers to the point where he is trusted to run an offense.
Trade Value
Looking at the recent Jake Fischer report, Holiday was reportedly in the Toronto Raptors’ sights for the price of the ninth pick (Collin Murray-Boyles) and RJ Barrett. If the Blazers chose to move on from Holiday, I’d do that deal even though I dislike Barrett’s remaining two years and $57.3 million. I’d also hazard a guess to suggest there would be other suitors interested in the savvy veteran.
As for Henderson, he’s still only two years removed from being selected with the third overall pick and is far from a bust. If the Blazers do move him, they’re not getting the same return they might have yielded for him on draft night in 2023.
But he’s still on a rookie-scale deal and, as such, is far from a negative value contract. I could definitely see one of the other 29 teams taking a swing. I just don’t know what kind of assets the Blazers get in return.
Conclusion
For Henderson, this is his season to prove he belongs in Portland. While I’m not wild about handing the point guard position over to two 35-year-olds, Henderson hasn’t shown he deserves a spot over the two veterans. Conversely, burying Henderson as a third-string point guard makes even less sense.
To this point in his career, Henderson has been a victim of circumstance. He was taken third in a deep draft, prompting the departure of one of his franchise’s greatest players — who has just returned.
I wonder what his status would look like if he’d been taken in the mid-20s by a team going through a less impactful upheaval. Unfortunately, the reality is now a little more sobering for Henderson. Show us something this season or serious decisions will need to be made.
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