What Does Neil Olshey Firing Mean for Damian Lillard and the Portland Trail Blazers?

Sean Highkin@@highkinFeatured Columnist IIIDecember 4, 2021

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PORTLAND, Ore. — Following a month-long workplace-conduct investigation, the Portland Trail Blazers fired longtime president of basketball operations Neil Olshey on Friday morning.

Now comes the hard part—figuring out where a franchise in full-on upheaval goes from here.

To understand where the Blazers might go, you have to understand where they've been. The last six months have seen a fourth first-round playoff exit in five years, an Olshey-driven coaching hire criticized for minimalizing the sexual assault allegations against Chauncey Billups, a summer of rumors about superstar point guard Damian Lillard's discontent with the direction of the roster, an assistant coach placed on leave after being indicted in an insurance fraud scheme, the departure of CEO Chris McGowan just last month, and an 11-12 start to the season—not to mention lots of empty seats.

That's before you even get to Olshey's unceremonious exit, which comes the morning after an embarrassing 114-83 loss at home to the 7-13 San Antonio Spurs. It also comes on the heels of the team's announcement on Wednesday that Lillard would be out for at least 10 days as he treats an abdomen issue that has bothered him for several years.

It is against this backdrop that the organization must now figure out how to fix a team that has stagnated and who will be the one to chart their path forward.

Joe Cronin, a front-office lifer who has been with the organization since 2006 and is in charge of managing the team's salary cap, was promoted to interim general manager on Friday. The team said in their statement announcing the move that it still plans to conduct a search for a permanent head of basketball operations.

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Whoever that person ultimately is will have a series of tough decisions to make.

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Since the start of training camp, Lillard has been pretty definitive about his desire to stay in Portland long-term despite persistent rumors to the contrary. All along, he's pushed for "urgency" in the front office to reshape the roster into a true championship contender. With Olshey now out of the picture and a fresh set of eyes evaluating the roster, previously held ideas about what was possible from a trade standpoint could be upended.

After Thursday's loss in front of a Moda Center crowd that was just over halfway full, Billups, in no uncertain terms, called out the effort of what has become a depressing and listless group to watch on a nightly basis. Their 10-game home winning streak heading into Thursday was offset by a 1-10 road record, and the team is still 29th in the league in defense despite Olshey's offseason insistence that their struggles on that end were due to coaching and not his roster.

Cronin is expected to address reporters in the coming days, which may give fans a sense of where he plans to take the team until a permanent replacement is named. Theoretically, everyone besides Lillard should be on the table in the upcoming efforts to upgrade the roster. 

That includes Jusuf Nurkic, the occasionally impactful but maddeningly inconsistent starting center set to hit free agency in July. That could mean youngsters Nassir Little and Anfernee Simons, who are beginning to break out just as they're up for new deals.

That could also mean CJ McCollum, Olshey's prized draft discovery. A McCollum trade has always been the obvious move to make for a meaningful upgrade, as his pairing with Lillard has repeatedly shown itself to have a hard ceiling. 

Olshey consistently refused to even consider it, preferring to swap out a Maurice Harkless for a Trevor Ariza or a Derrick Jones Jr. for a Larry Nance Jr., rearranging deck chairs on a ship perpetually headed for a seventh seed and a first-round exit.

Maybe the long-speculated-about McCollum-for-Ben Simmons deal becomes a serious possibility now that the Blazers' head decision-maker won't be staking their entire professional reputation on this backcourt.

"We give up size every night," Billups said last month before a home win against the Toronto Raptors. "We are a small group, especially at 1, 2 and 3. They are all pretty much 6'3"."

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The issue of size with Lillard, McCollum and Norman Powell in the starting lineup is one many around the Blazers have pointed out for a long time, but one that Olshey in June characterized as a false media narrative that "Dame gets frustrated with you guys talking about."

It's too early to seriously evaluate the job Billups has done in his first season as a head coach, good or bad. Olshey put him in a tough spot by placing all the blame for the team's poor defense and disappointing playoff showings at the feet of former coach Terry Stotts rather than seriously overhauling the roster. Billups knows it, too. Maybe the next general manager will give him a lineup that allows him to make the mark he wants to make as a coach.

It's been obvious since the death of longtime governor Paul Allen in 2018 that the Blazers have needed wholesale changes to build a true title contender around Lillard. That was never going to happen with Olshey in charge. Short of Allen's sister, Jody, selling the team, Olshey's exit is the single biggest move that could have ensured at least a chance at giving Lillard a team worthy of what he's built in Portland.

Now, it's up to the as-yet-unsettled new management to deliver on it.

Sean Highkin covers the NBA for Bleacher Report. He is a graduate of the University of Oregon and lives in Portland. His work has been honored by the Pro Basketball Writers’ Association. Follow him on TwitterInstagram and in the B/R App.


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