As Damian Lillard enters his tenth season with the Portland Trailblazers, one thing above all sets the tone of his career arc to a disappointingly flat level: nearly all of these campaigns have been, at their bottom line, the same. As the Rookie of The Year in 2013, Lillard found his pace on a team in transition, one that didn’t make the postseason. But after that, the Blazers were plucky “dark horse” contenders the rest of the way. Over the next eight years, Portland was dispatched in the second round of the playoffs twice, the first round five times, and the Western Conference Finals just once. Three of these seasons ended in a sweep, but only the most recent one can be definitively labeled as an underperformance.
The Blazers’ 2021 first round loss to a badly hobbled Denver Nuggets squad brought Lillard’s career into jarring new context. Never before had one of his teams lost because of… ambivalence? Lack of proper logistics? Boredom? It’s hard to say what exactly undid the Blazers against a team playing Austin Rivers and Facundo Campazzo thirty-plus minutes per night, with some Markus Howard minutes sprinkled in for bad measure. But certainly some blame lies with the organization for putting a bullseye on now-fired head coach Terry Stotts mid-season; rarely does such an internal designation, made loud and public, inspire a roster to be their best selves.
Following Stotts’ exit and the bloated controversy around his replacement Chauncey Billups—not to mention all the acrimony around the almost-hired Jason Kidd, who is now with the Dallas Mavericks instead—Lillard seems to be at a crossroads with his team. Through a series of hazy reports too frequent and well-developed not to be considered at least smoke, many are wondering if there is a fire that could send the perennial All-Star out. “Mixed messaging” is the best we can confidently make of Lillard’s approach thus far, but it’s clear the Blazers’ offseason moves (re-signing Norman Powell and bringing in Cody Zeller, Ben McLemore, and Tony Snell as minimum-contract reserves) aren’t helping to keep him put.
These are status-quo-preserving moves. And the myth around Lillard as an annual but unthreatening can’t-miss playoff gunslinging exhibitionist is set to ossify if he goes through yet another first- or second-round exit. This would hardly be a terrible legacy, to be sure—Dame Time, as it is known, is one of the more unifying watching experiences in pro basketball, and has been for years. Arguably the most clutch player of this entire NBA era, Lillard frequently reaches a level of accuracy and moxie from deep, in the most high-leverage moments, and this is, as a piece of entertainment to behold, not unlike Keanu Reeves as Neo, undoing an endless army of Deep State Computer Men in the Matrix franchise.
Something about the fact that he always ultimately loses, too, makes these ballistic displays all the richer. It makes him more of a hero to remain David and never become Goliath, staying faithful to the franchise that drafted him. Putting on such an incredible show in the service of a perpetually decent, rarely title-contending franchise has given a glow to Lillard for long enough that for many, it won’t ever go away. But in the present, the repetitive nature of the Blazers’ failures seems to be grating on Lillard as he peddles lukewarm half-measures about his future in Portland. There is never enough alongside Dame to complement what he does and fill in what he doesn’t do; never enough backcourt or wing defense, never enough extra playmaking to let him roam as the true score-first combo guard that he is.
The flaws in Lillard’s game should be noted with some emphasis. He really doesn’t play defense, and as his star has grown to a size that makes him more important than any coach, the Blazers’ offense seems to be more about his feel for the moment than any kind of dynamic, motion-friendly system that would reliably create easy looks for everyone else. This is fine and well when you can penetrate and pass like LeBron James, but Lillard is mostly a high-effort perimeter specialist whose greatest gift to his teammates is his gravity. Something more formal needs to actually be done with the extra attention he receives from defenses, though.
But because Lillard is probably the best at the specific, highly valuable thing that he does (score efficiently and at volume, and often being even better at this in the closing moments of a game), the Blazers would be wise to have built around his shortcomings sometime between when they became obvious—a while ago—and now. Instead, they have kept Lillard together with C.J. McCollum, a guard with a slightly different but mostly similar and worse version of Lillard’s impact, who hardly complements him at all.
McCollum is the Blazers’ second-biggest contract, and their most important potential trade asset when it comes to a road forward with a currently disgruntled Lillard. Any reasonable conversation about the Blazers taking a meaningful step forward with Lillard begins and ends with breaking up this pretend superstar duo, and at minimum trading McCollum for someone whose game does more to shore up Portland’s glaring weaknesses. To proceed any other way is foolish and hubristic. Lillard will, one way or another, probably leave in a scenario that involves McCollum staying. Lillard knows this, but saying this about the most reliable teammate of your career is awkward, and not really his job.
It is possible that, contrary to how he is signaling, Lillard will endure his organization’s imperfections and stick with what isn’t totally working, content to pour all his power into a cyclical ballad about how the little guys can never be amazing enough to overcome the big boy advantages elsewhere. This isn’t likely, but again, it is possible: this bittersweet tune is, after all, a song he has perfected. Whether he ever learns to sing another is the question at the heart of the odd, unclear place he is with his team right now.