Breaking down all the breakdowns that have taken place in Portland over the last six months could easily take six years.
Three weeks after the Blazers—the stalest team in the league—parted ways with longtime coach Terry Stotts in June, they hired Chauncey Billups, a respected ex-player and analyst, who’d faced a sexual assault allegation from 1997, one he never faced charges for and has said was consensual, but he reached an out-of-court settlement three years later.
At Billups’s introductory press conference, general manager Neil Olshey, who hired Billups, said the team looked into the allegations against Billups and hired a firm to investigate the merits of the case. Asked what that investigation uncovered, Olshey said, “That’s proprietary. … You’re gonna have to take our word that we hired an experienced firm that ran an investigation that gave us the results.” (A number of parties involved in that case—including the then district attorney and Billups’s attorney from back then—told a Portland news outlet that they hadn’t heard from the Blazers as part of whatever investigation that took place.)
Fast forward to November, and Olshey—the man who told us to take him and his organization at their word—was reportedly at the center of an investigation into the nature of the team’s workplace environment, one that eventually resulted in Olshey’s being fired last week for violations of the Blazers’ code of conduct.
All of which explains why it was never acceptable for Olshey to ask nor expect reporters—let alone die-hard fans, or survivors of sexual assault—to merely take the team’s word for anything of that nature. Especially not when the person who pulls the trigger on the hire then is more or less disgraced a few months later on the issue of workplace culture.
The notion of having a potentially toxic person make a coaching hire that has a potentially toxic element to it calls everything into question. It ultimately serves no one well, from the fans, media, the Blazers organization, or even Billups, who now may end up with a permanent boss less personally vested in his vision and development as a young coach.
Joe Cronin, previously the player personnel director, has been tapped to serve as the interim general manager, and he has an on-court mess on his hands. It may not exactly seem that way given that he’s overseeing a small-market club that owns the NBA’s longest-running postseason streak, at eight years in a row, and has a perennial All-NBA point guard on the roster.
But the devil is in the details.
Yes, the Blazers make the playoffs every season. But in those eight consecutive appearances, they’ve won just four series. Only in one of those years, in 2019, did they make it past the second round. And for how great the undersized Lillard has been for years—with countless gestures down at his wrist to denote “Dame Time,” and unforgettable, series-ending buzzer beaters—he’s in the midst of the worst season of his career by far and is currently out of the lineup with abdominal tendinopathy.
There’s a reason Lillard finds himself at the center of more ESPN Trade Machine deals than anyone else at the moment: The 31-year-old’s team, currently 11–15, seemingly hit a wall years ago, yet has made no real push or roster alteration to break through or around it.
Over the past 30 years, just four NBA duos have played nine seasons together without ever reaching the NBA Finals, according to data from Stats Perform: Muggsy Bogues and Dell Curry in Charlotte; Shawn Bradley and Michael Finley in Dallas; Mike Conley and Marc Gasol in Memphis; and Lillard and CJ McCollum in Portland. (Along those same lines, Jusuf Nurkić, Portland’s starting center, has been with the Blazers for the past six years.)
Lillard and McCollum bring plenty of scoring firepower. But the starting backcourt has always lacked the size or defensive chops to get consistent stops. Opposing teams see no resistance when it comes to getting into the paint, shooting 50% on runners—the highest mark in the NBA, per Synergy—against Portland. Opposing teams hit almost 39% of their triples against the Blazers, the highest mark in the league. Opposing teams have the highest effective field goal rate in the league against the club. All of which perhaps makes the next stat unsurprising: Statistically, the Blazers own the worst defense in the entire NBA, something that’s been true—or if not, very close to it—for the better part of the last three seasons now.
For the longest time, it’s been clear that a shakeup is needed. In Lillard and McCollum, the team generally has no problem scoring. But it miscasts Robert Covington—a great help defender, but one who’s long been overrated as a one-on-one stopper against elite wings—and finds itself out of alignment when teams swing the ball on offense. (Opposing offenses use more of the shot clock against Portland than any other team, per Inpredictable. But it makes no difference, with the Blazers unable to get stops.)
The most obvious fix would be to deal for Ben Simmons, who would theoretically give the Blazers the star defender they’ve long lacked while also giving them a valuable offensive weapon that approximates what Draymond Green does in the short roll with Golden State. Much like Stephen Curry, Lillard’s 35-foot range forces opposing defenses to send occasional half-court traps, forcing him to surrender the ball to someone who’d be playing downhill against a 4-on-3 scenario. Between the elite passing, and the athleticism that allows him to get a head of steam toward the rim, we know those are things the 6' 10" Simmons can do.
Of course there would be questions to ask before making such a deal. Is ownership comfortable with an interim general manager pulling the trigger on a deal for that much long-term salary for a player who’s showcased shortcomings underneath the brightest lights and been at the center of a headline-grabbing standoff with his team all season? (If the idea is for Portland to eventually find a permanent general manager instead, perhaps you don’t want the interim making a deal of that magnitude.) Does Lillard actually prefer Simmons to someone like McCollum—currently out with a collapsed lung—as has been reported?
And beyond that, how desperately does the organization need to seek Lillard’s sign-off? Certainly, the team positions itself better if it’s in step with what Lillard thinks and feels. But if the team ends up standing pat throughout the rest of this season and has no clear path upward this coming summer, the Blazers would be doing themselves a disservice to not at least explore what the market for a player like Lillard would yield.
No, the people of Portland wouldn’t like losing the face of its franchise, one Lillard genuinely seems proud to represent, regardless of who all he plays alongside. It wouldn’t spark a flurry of ticket sales and would likely have the opposite effect for one of the NBA’s smaller markets.
But at best, things in Portland have been stale. At worst, aspects of the club’s operation have been toxic. Olshey is out, but major roster changes seem long overdue as well. If not involving Lillard himself, then at least something that gives him a real, fighting chance to be part of a better-than-last-place defense and a team that can consistently make it out of the first round.
Anything less than that, and it continues to feel like everyone involved is merely making the eventual Lillard Band-Aid removal from Portland far more painful than it ever had to be.
More NBA Coverage:
• NBA Mailbag: Damian Lillard's Future With the Blazers
• NBA Power Rankings: Bucks, Bulls Rise in the East
• NBA Trade Ideas: Can the Warriors Land Sabonis?
• The End of the Neil Olshey Era Leaves Blazers in a State of Disarray