Yesterday the Portland Trail Blazers reunited with Damian Lillard, welcoming the former franchise superstar back to Rip City at the price of $14 million per year for the next three seasons. This comes on the heels of Lillard being bought out by his former team, the Milwaukee Bucks, following an ACL tear suffered during the 2025 NBA Playoffs.
Reactions to the move have been overwhelmingly positive in Portland. Today we’re going to delve a little deeper, asking who will benefit from the reunion and who might be smiling on the outside but thinking harder on the inside this morning.
Winner—Damian Lillard
Damian Lillard would no doubt rather have remained healthy than suffer a year-long injury. But if that unfortunate event had to occur, this was probably one of the more positive outcomes. He gets to rehabilitate in Portland, close to his family. His reputation gets rehabilitated instantly, as he resumes the mantle of hero, leader, and shining star. He did not have that same cachet in Milwaukee, where his effectiveness was questioned and where, ultimately, his teams failed to win. Lack of victories in Portland will not change public perception of him as a hometown idol.
Just as clearly, Lillard has come out of this situation well-compensated to the extreme. First, he signed a maximum contract extension…the least controversial of the financial windfalls that have come to him lately. Then the Bucks bought out that same contract, a historically-huge amount, at least partially because Lillard would remain on the sideline for most of a year (at minimum) recovering from his injury. Then, in a summer when young, talented, fully-functional free agents are signing for lesser amounts in a weak market, Lillard and the Blazers agree to a full Mid-Level Exception with three seasons guaranteed, a no-trade clause, and the last year on a player option just in case. Lillard has the NBA’s version of the Midas Touch right now, a great cushion to fall back on as his career closes.
Winner—Trail Blazers PR and Fans
The Blazers have been slogging along since they traded Lillard back in September of 2023, but they’ve been the pro basketball version of a tree falling in the forest with nobody to hear. The biggest national smash they’ve made is probably drafting Yang Hansen in the 2025 NBA Draft, that because of the surprise factor more than anything else.
It’s not just that Portland’s results were muted, mostly losses and minor transactions. They had nobody to speak up when they did something notable. An engagement ring setting without a diamond, they sat in the back of the case, operational but empty, waiting for life.
Damian Lillard is, was, and will always be a glittery gem. Need a quote? Go to Lillard. Need someone to drum up interest in your team? Put a microphone in front of Lillard. Need a poster to hang on a billboard? Hi, Dame! Smile!
For years, Damian Lillard put a bright face on mediocrity in Rip City, dressing it up so effectively that most Blazers fans treat it like a Golden Age despite zero rings, zero NBA Finals appearances, and only one Western Conference Finals trip, a series from which the Blazers got swept.
Yesterday’s reaction to his return could not have been bigger if he were fully-operational and coming off of an All-Star season. Most Blazers fans skipped right over the part where he won’t take the floor for a year and ran straight into the, “Dame’s back! Everything is right with the world!” camp.
This isn’t even dressing up mediocrity. It’s resurrecting the dead. Damian Lillard is enough of a PR miracle in Portland to do just that. And the energy surrounding him won’t be dimmed by any pesky on-court results until he actually returns.
In this way, 35-year-old, injured, and potentially slumping Damian Lillard is just as good as the earlier version. It’s a gift, and a celebration, that Portland didn’t expect to have. Whatever actual results come from the move, this benefit is clear and sorely-needed.
Loser—Scoot Henderson
One of the reasons the Blazers traded Lillard back in ‘23 was their shiny new draft pick, the much-ballyhooed Scoot Henderson. Henderson developed into a decent player last season after a disastrous rookie campaign. Debate still rages whether he’s on the cusp of assuming a starting role—and the reins of the franchise—or whether he needs more work.
One line of thought says that Henderson could not have better mentors and tutors than Lillard and Jrue Holiday, the other veteran guard the Blazers acquired this summer. On the surface, the new point guard triad looks good. You couldn’t ask for flashier names.
Maybe that mentorship will develop. There’s a lot of noise in the hierarchy, though. Usually when the upward mobility ladder gets top-heavy, young candidates on the bottom run have problems ascending past their more-experienced colleagues. That’s a risk for Henderson as well.
Henderson has a season to prove himself with only Holiday in the mix. If the young guard can achieve liftoff, all will be fine. Between injury and age, Lillard will have an altitude cap when he returns. If Scoot has already exceeded it, he’ll have that airspace alone.
What happens if Henderson really does need to develop, though…if he needs the mentorship that many are anticipating? Basketball is an experiential field. You can only absorb so much academically. The best results come when you take the floor as yourself, get to make decisions (and mistakes) freely, and develop court sense while playing instinctively, lightning-quick and without regret.
Imagine learning to drive with TWO dads, both world-class, neither subject to criticism or dismissal, offering advice from the side and back seats. Even better, imagine developing your performance chops on stage at the county fair with Billy Joel and Elton John in the wings, offering advice. Also, pretend the whole crowd knows they’re back there.
Even before the Holiday and Lillard acquisitions, my gut feeling was that the relationship between Henderson and the Blazers was on uneven ground. That’s not anything but a personal analysis; take it for what it’s worth.
I understand that both veteran guards arrived via opportunistic circumstances. The progression wasn’t A to B to C. The Blazers had the chance and jumped at it. That wasn’t necessarily because of Henderson, rather regardless of him.
I don’t think Henderson’s path forward in Portland is clearer now than it was a month ago. Less so, in fact. If Head Coach Chauncey Billups can avoid the temptation to limit Scoot in favor of his more accomplished teammates, if Scoot can get teammates to gel around him, if Scoot can finish developing his professional skills and confidence himself, and if the Blazers succeed, Lillard and Holiday will probably fall into place without too much fuss. If any of those things fail to happen, the temptation for dad to say, “Let me drive for a minute,” is going to be strong. That is not going to be good for Scoot’s development.
Winner—Joe Cronin
For years, Blazers General Manager Joe Cronin has done mostly blue-collar work from his lofty perch. His biggest move was trading Lillard in the first place, a necessary and relatively-unspectacular process of acquiring future assets in the wake of a disgruntled superstar. Acquiring Jerami Grant and Deandre Ayton, re-signing Anfernee Simons…the moves were significant, but didn’t make big splashes. Despite the Blazers welcoming successful young players Deni Avdija and Toumani Camara over the past two years, many fans were wondering if Cronin was capable or willing when it came to big-time moves.
Technically speaking, Cronin still hasn’t taken a huge swing. He traded down and executed a draft pick to get Yang Hansen. He signed Lillard after Lillard had been waived by another team. These are mundane operations.
The Splash Quotient has gone WAY up for Cronin since the NBA Draft, though. Holiday was a reasonably big name to trade for. Yang made national news when drafted and largely backed that up in Summer League. Lillard ended up frosting and decorating that cake in world-class fashion.
Cronin may not be a markedly different GM now than he was in May, but he’s bought himself some grace and appreciation from Blazers fans and, for better or worse, put a high-profile stamp on his tenure. That’s been a missing ingredient heretofore. It’s present in abundance at this juncture.
Loser—Chauncey Billups Maybe?
At first it seems ridiculous to say that Blazers Head Coach Chauncey Billups might be impacted negatively by adding Lillard and Holiday to his roster. More players equals more options. More depth equals more resilience. The Blazers have sorely needed both.
It’s not that easy, though. Coaches live and die by two things: wins and expectations.
Holiday and Lillard have sent the team’s profile through the roof. They are Olympians, All-Stars, paragons of their styles of play, and one of them is considered among the best players the franchise has ever seen. Whatever logic or reason claim, expectations for the Blazers will soar over the next season.
Realistically, though, both guards are in their mid-30’s, production has dropped for each in recent years, and Lillard won’t even play until he rehabs from injury. It’s like erecting a big McDonald’s sign but having no fries and only an eighth of a Pounder. That may get fixed eventually, but in the meantime, who are you going to get mad at? The manager.
Billups’ win-loss record is already bad…historically so. When the actual games start, if the Blazers don’t start winning, publicity and flashiness are going to seem ironic. More to the point, they might be used as further evidence that coaching, not talent, is to blame for Portland’s woes.
Throw in a little bit of that “two dads in the back seat” vibe for the first-team-ever coach and you don’t necessarily have a rosy picture forming for Billups. It could work. Maybe he’ll come out looking like a genius. But if not, Lillard and Holiday don’t necessarily erect a guardrail on the side of Billups’ road. They might make the pavement slightly more slippery, at least when it comes to reputation and expectations.
To Be Determined—The Actual Blazers
If you clear away all the hype and celebration, the Blazers just got a fairly-seriously injured, 35-year-old star guard whose value comes on the offensive end and whose gravity is larger than that of the rest of the roster combined. That’s not an automatic recipe for success. The recovered Lillard isn’t going to be better at defense than he was prior to the injury. We don’t know for sure how much his offensive explosiveness will come back. There’s a chance that this signing becomes much ado about…not much. If it’s going to be more, both Lillard and his teammates will need to prove it.
That’s not an indictment of the move. It was a reasonable thing to do, at least for now, regardless of outcome. But the publicity and goodwill surrounding Lillard’s signing is at a supercharged 10. The actual benefit on the court is not likely to get anywhere close to that.
If Lillard can give what any other MLE-level player would be expected to, this should turn out OK. The potential variance ranges higher that than, but it also dips below. I’m not sure anybody is sure what will come of the move in practical terms. It just feels good.
For now, that’s enough. There have been few enough reasons to celebrate in the last half-decade in Portland. Let the banners fly. The chips are going to fall where they may anyway. Until then, we’re all winners, right?
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