Prior to taking the job as general manager of the Portland Trail Blazers, Neil Olshey walked into a franchise that had replaced its lead decision-maker three times in three years. In fact, Kevin Pritchard, who built a 54-win team around Brandon Roy, still ran the Blazers 2010 NBA Draft while knowing it was his last day on the job.
Simply put, the Blazers general managing position was a revolving door until Olshey took the gig in 2012. Since then, he's been the second-longest tenured general manager in franchise history, making the playoffs all but one season and even making the Western Conference Finals in 2019.
However, now amidst rampant speculation that Damian Lillard is eyeing other destinations to play with noise to back it up, Olshey finds himself running the most important offseason in decades for Portland.
Talkin' Blazers co-host Dan Sheldon says Olshey brought this upon himself, valuing his job security over winning at the highest level with an MVP-caliber player in Lillard.
"I think up to this point, it's been establishing some stability not only for himself but for the organization," said Sheldon. "I think Olshey has always defaulted to stability over taking that big swing because he knew if he swung and he missed, he's fired and he's got to look for a new job.
"He valued his stability and knew it would be good enough for everyone involved... Up until now, he could get away with it because he kept quoting year after year 'We keep making the playoffs', well in some places that's not good enough."
"You're supposed to make the playoffs, you have a top-ten player in the NBA. Stop it," added Channing Frye.
Since the death of Paul Allen, Olshey's viewed as prioritizing his job security above all else, failing to own up to mistakes publicly such as claiming Portland's 29th-ranked defensive rating "was not a product of the roster" he built after giving coach Terry Stotts a bench lineup of Anfernee Simons, Carmelo Anthony, and Enes Kanter.
Olshey has already survived monumental failures such as giving both Allen Crabbe and Evan Turner 4-year deals both worth over $70 million in 2016, failing to pair Damian Lillard with an All-Star teammate while the NBA has seen unprecedented movement of superstars and leaving the 2017 NBA Draft drafting two busts despite three first-round picks.
"The draft isn't for quick fixes and positional need," Olshey said after the 2017 NBA Draft. "The draft is for the long-term. This is about the next 12-15 years."
Both of those "long-term" assets, Zach Collins and Caleb Swanigan, failed to get even a qualifying offer from Portland. Forget the next 12-15 years, Olshey's recent draft picks barely helped the franchise on rookie deals.
Meanwhile, while Olshey has shied away from doing what it takes to trade for unhappy superstars such as Jimmy Butler (traded twice on his last deal), Kawhi Leonard, Paul George, James Harden and more, now the Blazers own franchise building block is more frustrated than ever.
"We didn’t win a championship, so obviously where we are now isn’t good enough,” Damian Lillard said after being eliminated in Game 6.
“I don’t know what a shakeup looks like or what changes will be made or could be made, but obviously as is, it wasn’t good enough. We came up short against a team without their starting point guard and shooting guard (Jamal Murray and Will Barton). ... Obviously, where we are isn’t good enough to win a championship if it’s not good enough to get out of a first-round series with two of their best three or four players not on the floor.”
Last week, Lillard said he hadn't made a firm decision on his future despite a four-year extension kicking in this season.
In fact, Dame put public pressure on Olshey to make moves this offseason so Lillard can win it all in Portland rather than demand a trade.
"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," said Lillard.
"We've made the playoffs all these years in a row. We're not a bad team, we're a winning team. We're in the playoffs every year. We got a great environment. We're in a great city... It's a lot of positives but I just think we've reached that point where it's like, 'ok but it's not enough.' Do we actually want to win it all? Is that what we're shooting for. We got to do things to show that. We got to put action behind that desire to win at that level."
Can Olshey deliver or will he run it back with a team who lost so badly to Denver, it caused Lillard to play for Team USA to be a part of winning?
"The fact that the season wasn't extended for me... leaving a sour taste in my mouth after losing so early to a team that was beat up and injured when I expected to win that series, it gave me that itch to jump back in and play and have that chance to win," said Lillard.
Ball's in your court, Neil.