Damian Lillard’s voice carries. That’s the privilege and power that comes with six All-Star berths and All-NBA selections, with perennial MVP candidacy, with an ever-expanding sizzle reel of cold-blooded crunch-time highlights. Lillard is one of the NBA’s highest-paid superstars: He’s one of just eight players to ink a supermax extension and is a crossover celebrity with multiple high-profile deals off the court, too. When rainmakers of that magnitude speak, everyone listens.
Lillard spoke after his Trail Blazers lost in the first round of the 2021 NBA playoffs to the shorthanded Nuggets. It was a dispiriting defeat: Portland dropped Game 5 in double overtime, despite Dame exploding for 55 points and 10 assists, and blew a 14-point second-half lead at home in Game 6 thanks largely to an inability to defend the pick-and-roll. He spoke plainly, calling on everybody in the Blazers organization to “look in the mirror, because we’ve constantly come up short [and] whatever it is we’re doing is not working.” He spoke directly, expressing doubt that replacing Terry Stotts with Chauncey Billups at the head of the bench—a coaching change that was a shitshow in its own right—is enough, on its own, to transform the Blazers.
“I don’t disagree that maybe Chauncey can really change our team and make us a better team and get us going in that direction,” Lillard told reporters last month while preparing to go to Tokyo with Team USA. “But I think if you look at our team as it is going into next season, I don’t see how you can say, ‘This is a championship team, we just need a new coach.’ ... Do we want to win it all? Do we actually want to do that? Then we’ve got to do things to show that.”
He spoke, essentially, to an audience of one: Blazers president of basketball operations Neil Olshey, who was hired in 2012 and made Lillard his first draft pick that same year. Olshey has shepherded the franchise through a run that has produced eight straight postseason appearances, but that has also resulted in more first-round exits (five) than playoff series victories (four). Olshey made clear when he fired Stotts that he believed Portland’s underperformance last season, particularly on the defensive end, was “not a product of the roster” he’d built, and that he believed a new coach and a new defensive approach could turn that roster into a bona fide championship contender. Lillard made clear—in that pre-Olympics press conference and also reportedly in “long meetings and back-and-forth text messages” with Olshey before it—that he disagreed, calling on the Blazers front office to “be more urgent about what our next step is, and how we move forward.”
While Lillard didn’t elaborate on his definition of “urgency,” he also didn’t sound overwhelmingly thrilled about a summer haul of re-signing Norman Powell for five years and $90 million and adding Cody Zeller, Tony Snell, and Ben McLemore for the veteran’s minimum. And so the NBA world waits for Dame to speak again—to see when, or whether, he’ll say the magic words and become the latest superstar to seek greener pastures in a league-shaking trade.
He hasn’t yet. Lillard, whose four-year supermax extension kicks in this season, said last month that he hadn’t “made any firm decision on what [his] future will be.” Multiple subsequent reports have backed that up, with ESPN’s Zach Lowe writing that “Lillard is not available, and has not asked for a trade,” and Stephen A. Smith describing Lillard on a recent episode of The Lowe Post as “incredibly reluctant to leave Portland.” Just this week, Lillard told viewers on Instagram Live that he’s “not leaving PDX—right now, at least.”
“I don’t think he wants to leave. He has built an empire here,” one Blazers executive told Jason Quick of The Athletic in July. “But we have to assume he is leaving to make sure he is not leaving.”
There’s the rub, though: Olshey’s offseason sure doesn’t seem like one conducted with a level of gravity commensurate with the existential threat of arguably the greatest player in franchise history leaving town for good. Which raises the question: Um, what are the Blazers doing, exactly?
The lack of resolution this summer leaves the Lillard situation hanging over the entire franchise like the sword of Damocles. But if the status quo holds, it’ll also give Olshey the chance to head into the season with Billups at the helm of the roster he’s constructed—one in which he evidently believes quite a bit—in hopes of achieving the sorts of championship-level results that might give the 31-year-old Lillard fresh faith that the rest of his prime has been entrusted to sure hands.
It’s an awfully bold gamble, but it might not necessarily be one that’s drawing dead. Olshey shipped Gary Trent Jr. to Toronto for Powell at the 2021 trade deadline in the belief that the longtime Raptors swingman would elevate Portland’s already-potent offense into the stratosphere. The post-trade returns bore that out: The Blazers led the NBA in points scored per possession after Powell’s arrival, and scored at an even higher clip during the first-round matchup with Denver. According to Cleaning the Glass, when the new-look starting five of Lillard, Powell, CJ McCollum, Robert Covington, and Jusuf Nurkic shared the floor during the regular season, Portland blitzed opponents by 14.2 points per 100 possessions—the second-best net rating of any lineup to log at least 750 possessions together—and nerfed the Nuggets by an obscene 20.8 points per 100 in the starters’ minutes in Round 1.
The issues came when the second unit entered—particularly on the defensive end, as Denver carved the Blazers to ribbons whenever Carmelo Anthony and Enes Kanter were on the court. Although both brought value on the offensive end and on the boards, the Nuggets were able to leverage their lack of foot speed in space to force Portland’s defense into rotation, creating open shot after open shot. Both will play elsewhere this season. Olshey’s betting that even if Zeller (perpetually plagued by injuries in Charlotte, but damn solid when healthy), Snell, and McLemore can’t quite replicate Melo’s and Kanter’s firepower, they’ll provide steadier defensive play and enough complementary shooting to help prevent leads from turning into deficits while the starters catch their breath.
Some semblance of addition by subtraction in the reserve corps—plus leaps forward from youngsters Anfernee Simons and Nassir Little—would be massive for the Blazers. A full season of Powell, who averaged 17 points per game as a hand-in-glove fit in Portland’s offense, should help, too. Combine those with healthier turns from McCollum, who was averaging nearly 27 points per game before suffering a foot fracture that cost him 25 games, and Nurkic, who missed 10 weeks with a fractured right wrist and in whose minutes Portland defended at a top-five rate, plus a hoped-for defensive improvement under Billups (who insists it will no longer be “optional to play hard defensively” in Portland), and maybe you can see the Blazers get out of the gates quickly in a West loaded with talent but lacking a runaway favorite. (You might need to squint a bit.)
Maybe that puts Portland in position to seize an opportunity in the run-up to the February trade deadline, where Olshey has taken some bigger swings in years past—landing Powell last season, Trevor Ariza in 2020, Nurkic in 2017, and Arron Afflalo in 2015—to round out the rotation. Maybe, if a few things break right, the Blazers can enter May with both the puncher’s chance that Dame always provides and the sort of balance and depth they’ve rarely brought to bear.
If you’re thinking that’s an awful lot of “maybe” on which to hang the future of your franchise, you’re not alone. But then, given the state of affairs and of Lillard’s patience, that’s just about all Olshey can still hang things on.
He fired the second-winningest coach in franchise history and hand-picked his replacement; if the Billups experiment goes up in flames, he’s extremely unlikely to get another crack at making the hire. He doubled down on his belief in the quality of the rosters he’s built, in spite of the recurring lack of balance and depth that has so often left the Blazers with no recourse but Bail Us Out, Dame.
He’s put together a team with eight players set to hit free agency in the summer of 2022 and where the only players on guaranteed deals extending beyond this season are Lillard, McCollum, and Powell … and yet, the Blazers as constructed still won’t have significant salary cap space next offseason, even with a skeletal roster, because those three guards are set to make $92.6 million in 2022-23 and $99.4 million in 2023-24.
The loss to Denver felt like it marked the end of an era, but it hasn’t marked the end of Olshey’s reign. That would likely change if Lillard asks out, though; it’s hard to imagine Olshey getting to stick around to sketch the blueprint for what comes next in Portland. Frankly, it’s hard to imagine much about what life for the Blazers would look like: Rebuilt around McCollum, Powell, and whatever high-end player/prospect they get for Dame (cough, cough)? Stripped down to the studs for a rebuild? (Portland does own all of its own first-round picks moving forward.) Some accursed middle path that leaves the Blazers wandering through the proverbial late-lottery desert, in search of a new north star to follow?
Maybe that’s why Olshey is standing so firm, why Lillard hasn’t yet raised his voice again, why the franchise and the franchise player are spending their summer in a staring contest. Frustrating though it may be, there’s a certain comfort in what’s familiar. On the other side of desperate all-in trades and magic words lies the unknown and, with it, the potential for irrevocable, discomfiting change. The principals in Portland seemingly aren’t all the way ready for that yet, and so we wait, ears open, for the words that would reverberate and change everything—for Lillard, for the Blazers, and perhaps for the power structure in a league that’s never been more all in.