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Will Neil Olshey’s Ouster Lead to the End of the Damian Lillard Era in Portland?

The longtime GM was fired after an investigation into the team’s workplace culture. With the Trail Blazers also struggling to stay in the playoff mix, will one of the steadiest franchises in the NBA finally opt for major change?

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The Trail Blazers fired Neil Olshey on Friday, ending the reign of one of the NBA’s longest-tenured top-level executives—and heightening the intrigue about what comes next for a franchise in tumult.

Olshey’s ouster comes on the heels of the resignation of Chris McGowan, the head of the business side of the Blazers, and four weeks after the team launched an investigation into “workplace misconduct” prompted by employee complaints about the environment at Portland’s practice facility. According to Chris Haynes of Yahoo Sports, the investigation began after staff members said they “have been subjected to intimidation and profanity-laced tirades, among other bullying tactics” over the past 10 years.

“He will talk to you however he wants and treat you however he wants,” a former Blazers employee told Jason Quick of The Athletic in a piece describing Olshey as “a full-time a–hole.”

The franchise on Friday declined to “release or discuss” the details of the independent inquest, but did explain that the firing was “due to violations” of the team’s code of conduct. It’s worth noting, though, that the decision also came the morning after Portland’s worst loss of the season: a 114-83 destruction at the hands of a Spurs team that entered Moda Center 6-13 and with the NBA’s no. 24 offense.

In fairness, the Blazers were without superstar centerpiece Damian Lillard, who’s out of the lineup for at least 10 days while he deals with lower abdominal tendinopathy, and lost replacement Anfernee Simons to a sprained right ankle early in the second quarter. There’s only so much grace you can extend, though: It was the Blazers’ fourth loss by 20 or more points on the season. Only the erratic Grizzlies and the no. 1 pick–chasing Magic, Pistons, and Thunder have more.

“My biggest concern at the moment is I want us to compete harder,” head coach Chauncey Billups told reporters after the loss. “I want us to be more competitive in every game. And I don’t feel like every night we do that. And that concerns me.”

The loss dropped the Blazers to 11-12, ninth place in the West. That’s probably not the return that team owner Jody Allen expected for a $137 million roster that could cost an additional $4.5 million in luxury tax come season’s end. The fact that it came at home probably didn’t help matters, either … especially considering it happened in front of more than 3,000 empty seats. Portland, home to one of the NBA’s most passionate fan bases, has ranked in the top 10 in the NBA in average home attendance for 13 straight seasons from 2008 through 2020. This season, though, the Blazers rank 13th, with the average crowd below 90 percent capacity for the first time since the 32-win 2006-07 season. The already-difficult job of selling yourself as a visionary leader capable of getting the franchise past internal strife and over the hump gets a lot harder once the gate receipts start to drop.

Whichever straw broke the camel’s back, the decision to fire the NBA’s third-longest-tenured basketball decision-maker—only Oklahoma City’s Sam Presti and Golden State’s Bob Myers have been with their teams longer than Olshey, whom the late Paul Allen hired away from the Clippers in June 2012—represents a significant shift for the Blazers. It could also serve as the impetus for a massive overhaul within a team that seems to have grown stale.

The Blazers had a .556 winning percentage under Olshey, ninth-best in the league in that span. They’ve made the playoffs for eight years running, the NBA’s longest active postseason streak. They’ve won 50 games four times, won four playoff series, and made the Western Conference finals once—in 2019, when Dame waved bye-bye to the Thunder and CJ McCollum said goodnight to the Nuggets before Stephen Curry put the Blazers to bed.

Those successes, combined with the ascent of Lillard to MVP consideration and folk-hero status, helped keep the dream of the ’90s alive in Portland—sustaining the belief that, with a couple of tweaks on the fringes of the roster and a little bit of luck come the playoffs, the Blazers could break through and return to the NBA Finals for the first time since Clyde the Glide still soared over the Pacific Northwest. The 2021 playoffs, though, served as a wake-up call. After the Blazers lost in the first round for the fifth time in eight years under head coach Terry Stotts, it was crystal clear that a change was needed.

Olshey responded not by pursuing a rotation-remaking trade, but rather by firing Stotts, the second-winningest coach in franchise history, and insisting that the Blazers’ failings—especially on the defensive end—were “not a product of the roster” he had built. He proceeded in the belief that a new coach and a new defensive scheme could elevate that roster—which led the NBA in points scored per possession after Olshey traded for Norman Powell, featuring a starting lineup that blitzed opponents by 14.2 points per 100 possessions during the regular season and hammered the Nuggets by 20.8 points per 100 in the playoffs—to its rightful place among the NBA’s true title contenders.

Toward that end, Olshey hired former All-Star point guard Billups to lead the team. The choice of Billups—who had never served as a head coach at any level—raised questions about the degree to which Olshey and the Blazers had investigated the 1997 case in which Billups settled a suit brought by a woman who said he sexually assaulted her.

At a press conference introducing Billups as the Blazers’ next head coach, Olshey insisted that the organization “took the allegations very seriously, and we treated them with the gravity that they deserve”—a process that included a background check and an independent investigation that “corroborated Chauncey’s recollection of the events that nothing non-consensual happened.” Pressed for more details on that investigation, Olshey termed its findings “proprietary,” and told reporters they were “just gonna have to take our word that we hired an experienced firm that ran an investigation that gave us the results we’ve already discussed.” A subsequent report by Oregon Public Broadcasting raised doubts about the “thoroughness and intent” of the investigation.

The Blazers pressed on, with Olshey praising Billups’s “natural gravitas, leadership skills” and “history on the defensive end of the floor.” Those traits, however, have not yet produced the designed improvements: Portland’s more aggressive defense still ranks as the third-worst in the NBA, and dead last in opponents’ effective field goal percentage. Asked recently about the challenges of stringing together stops, Billups told reporters, “We give up size every night, man.” When it comes to finding sustainable success on defense with a three-guard starting lineup of Lillard, McCollum, and Powell, plus the 6-foot-3-or-smaller Simons, Ben McLemore, and Dennis Smith Jr. off the bench, Billups said, “We’ll see.”

Director of player personnel Joe Cronin has been elevated to interim GM, and will try to pull Portland out of its early-season nose dive. Cronin, reportedly the team’s “salary cap guru,” isn’t expected to be a candidate to replace Olshey full time; early names on that list include executives Tayshaun Prince of the Grizzlies, Brent Barry of the Spurs, Marc Eversley of the Bulls, Scott Perry of the Knicks, and former Celtics GM and Oregon native Danny Ainge.

In the short term, we’ll see whether Billups can find a way to get Lillard (shooting just 40 percent from the field and 30 percent from 3-point range), McCollum (43 percent from the field and 70 percent from the foul line), and center Jusuf Nurkic (averaging a double-double, but very up and down in terms of his defensive work) on track—and, perhaps, find another way to motivate his struggling veteran-laden team than repeatedly calling them on the carpet. If he can’t, and if the Blazers continue puttering around the bottom of the play-in mix, or worse, in the lead-up to February’s trade deadline … well, then the calls to blow up an Olshey-constructed roster featuring eight players set to hit free agency next summer, with $92.6 million owed to Lillard, McCollum, and Powell in 2022-23, could reach an overwhelming volume.

If Cronin’s empowered to make deals while wearing the interim tag, perhaps he tries to tinker around the margins, leaving the major core pieces alone and seeing what sort of value the league places on vets like Robert Covington and Larry Nance Jr., or youngsters like Simons and Nassir Little. Maybe the Blazers’ new brain trust thinks bigger, taking a long look at a move Olshey had reportedly long been loath to make: trading McCollum in pursuit of the sort of player who could better balance the roster, hiding Portland’s defensive flaws while accentuating its playmaking talent. (Cough, cough.)

Or maybe this is it: the reset button, the clean break, the inflection point when Dame decides it’s time for both him and the Blazers to start over.

Lillard made it clear this summer that he wanted everybody in the Blazers organization to “look in the mirror, because we’ve constantly come up short.” He expressed doubt that replacing Stotts with Billups would be enough to turn Portland into a championship team. He feels urgency: to fix what’s broken and to win a title, or at least meaningfully compete for one. What if Dame, who’s in the first year of a four-year supermax extension, looks at the lay of the land post-Olshey and decides that the time has finally come to say the magic words and become the latest superstar player to push himself to a ready-made title contender? (This is where we remind you that in about two weeks, on December 15, the majority of players who signed free agent contracts last offseason become eligible to be traded, opening the door to all sorts of prospective Lillard suitors and deal structures previously unavailable to the Blazers.)

That’s a whole lot of maybes, ifs, and contingencies; there’s too much in flux in the hours after Olshey’s exit to predict with much confidence the directions in which the next round of decisions might go. This much, though, is certain: Change is coming to Portland. The only questions now are how much, who’ll be left behind to build something new, and whether those who depart could change the shape of the league.

An earlier version of this piece incorrectly referred to Terry Stotts as the winningest coach in Trail Blazers history; he is second in all-time wins.