The End of the Neil Olshey Era Leaves the Trail Blazers in a State of Disarray

Olshey was fired by Portland on Friday. Whoever succeeds him will have plenty of problems to solve.

The beginning of the end for Neil Olshey came last June, when the embattled Blazers GM stood in front of reporters to announce the firing of Terry Stotts and attempted to convince them it was Stotts, not the roster, that was the problem. The defense was better than the cellar-dweller it had been the last two seasons, Olshey insisted, and the core of the team—specifically Damian Lillard and C.J. McCollum—could still be molded into a winner.

Six months later Olshey is gone, though not—at least officially—for the Blazers' current mediocrity. Portland terminated Olshey on Friday after an independent investigation revealed evidence of a toxic work environment. The team declined to offer specifics and says it will not release the report, but for weeks investigators at O’Melveny & Myers have been interviewing current and former employees, gathering evidence against Olshey. Many of the stories were similar, sources familiar with the investigation told Sports Illustrated: Olshey could be verbally abusive, sometimes publicly, creating what at times was a palpable tension inside the Blazers practice facility.

Olshey is out, Joe Cronin (for now) is in, and the bulldozer may not be far behind. A quarter of the season is gone and the Blazers are no closer to winning than they were last season. Thursday night’s 31-point loss to San Antonio dropped Portland to 11–12 on the year. The defense remains one of the league’s worst. They have a sterling 10–2 record at home and a dreadful 1–10 mark on the road. Chauncey Billups’s disciplined, structured style has yet to take hold on a roster that had grown used to Stotts’s free flowing system. Lately, Billups has taken to publicly pleading with the team to compete harder.

“I think pretty good,” Billups said this week, in response to a question about how his coaching has been received. “But at the end of the day, it’s not easy. It’s not easy all the time to hear when you are not doing what you are supposed to do, especially from the coach. All I care about is I believe we should play one way. I know what wins, I know what’s important. When we don’t do it, obviously I’m going to always bring it to the table, to those players, to those people. And I know it’s not always going to be well-received.”

Whoever takes over in Portland—Yahoo! Sports reported that Bulls executive Marc Eversley and Knicks GM Scott Perry could be in the mix, and you can be sure Danny Ainge's name, an Oregon native and an ex-Blazer, will come up—can only reach one conclusion: This team needs to change. It’s nobody’s fault. This group has simply plateaued. There’s no fringe nibbling deal that will vault the Blazers into conference contenders, no tweak that will elevate them into a top spot. We know, because they have tried.

Olshey was long reluctant to pull the trigger on franchise-altering moves, in part because doing so felt like an admission of failure. Olshey is extremely proud of his draft record. He plucked Lillard with the sixth pick in 2012. He took McCollum, another mid-major star, with the 10th pick a year later. He drafted them, invested in them. And over time he became too attached to them. Instead of shaking things up, Olshey spent lavishly in recent years trying to find the right pieces to put around them.

A new GM needs to take an objective look at this roster. There’s a world where a McCollum for Ben Simmons swap could be available, and if it is, the Blazers should pounce on it. Simmons is damaged goods right now, but at his best he is a dynamic playmaker, one capable of defending four positions.

There needs to be a serious conversation with Lillard, too. Lillard is 31 and, even with this season’s sluggish start, is still among the NBA’s best. But the Blazers aren’t winning anything the next few years. Lillard will likely be looking for another max-level extension next summer that tacks two years and a $100 million more onto his deal.

Does Portland want to commit to a player beginning to show wear from his oversized workload?

Does Lillard, fiercely loyal, want to spend his remaining years on a fringe contender?

There are big decisions ahead in Portland. The Olshey Era had great moments on the court (a trip to the Western Conference finals in 2019) and a run of playoff appearances (eight, the longest active streak) but what’s left is a team in need of an overhaul. It ended ugly for Neil Olshey in Portland. But one way or another, it was going to end.