Neil Olshey firing is only going to prolong the wait for your Dame dream trade

How did it come to this? The better question is: Why did the firing of Neil Olshey take so long?

How did it come to this? The better question is: Why did the firing of Neil Olshey take so long?
Image: Getty Images

Let’s try an exercise. Something happens to the Portland Trail Blazers franchise, and they don’t immediately try to trade Damian Lillard. It’s to the point that I wouldn’t be shocked if media outlets have a pre-written template for Blazers stories.


“The Trail Blazers look _____, they should trade Lillard.”

Sad to say, Neil Olshey getting fired is going to keep Dame in the Pacific Northwest until a new GM is hired.

Lillard may not be there next season because Portland’s roster, as it stands, is irredeemably flawed. However, the next person in charge of team management hasn’t even been hired yet, so expecting the franchise to trade the best player in its history, who also happens to be injured right now, before the new GM is onboarded, is wishful writing.

I’m going to speed through the Olshey timeline because he should’ve been fired before ownership “discovered” a reason to let him go without pay. Hired in 2012, the same year Lillard was drafted, Olshey had a couple hits — CJ McCollum and Jusef Nurkic — but far more misses: the Evan Turner contract, the Meyers Leonard contract, the handling of the Chauncey Billups hiring, throwing Terry Stotts under the bus, and, most importantly, flat out failing to build around Lillard, even after signing him through 2025.

I like Norman Powell, but going even smaller when you’re already small in a league that hasn’t seen an undersized backcourt lead a team to a title since Isiah Thomas and Joe Dumars (both defensive-minded players, by the way) nearly 30 years ago was a shit bet. The only other contemporary team built around a small guard not named Steph Curry (who’s not even really small) that saw a Finals was Allen Iverson’s 76ers, and they lost in five.

That Olshey didn’t want to hear it/was in denial/was an asshole is why I’m writing this today. Had ownership listened to @fireneilolshey when it was created in 2018, the Dame situation could’ve been avoided. Now, it’s not only highlighted, but exacerbated by coming in the middle of the season, after a predictably slow start, when there’s another win-now team hovering around .500, dealing with an injured superstar, and trade demands.


For Portland, it just so happens that the injured superstar also is the player who allegedly demanded a trade. To add anxiety, the team is in the luxury tax and owned by someone who may not want to pay it.

It would’ve been nice to have a capable general manager who didn’t simply reshuffle the deck, hoping for a favorable playoff draw. The 2018-19 run to the Western Conference Finals is sadly the outlier in this Portland team’s postseason history under CJ and Dame.


The timing of the Olshey firing was bad for Portland and bad for all the people who want Lillard traded, including Daryl Morey’s arrogant ass. Wasting a superstar’s prime makes any superstar mad and leads to fanbases understanding and eventually accepting that moving on is what’s best for their favorite superstar. That’s why the previous best Trail Blazer ever, Clyde Drexler, was traded and fans still love him.

If Portland shipped out Dame tomorrow, he’d get a king’s welcome every return game because Blazer faithful agree Olshey has severely hampered his chances of contending. But he’s not getting traded tomorrow. No Blazer is getting traded tomorrow. Because they don’t have a GM, and who the hell knows when they’ll hire one or even be able to hire one if he’s GMing for another team right now.


However, the only way Lillard stays long term is if the Trail Blazers remedy the issues ailing the team as soon as possible because as constructed this is a hostage situation, and Stockholm syndrome isn’t a viable out.

Forgive me for not writing the obligatory “Is this the end of Dame time in Portland now that Olshey is fired” piece. Portland fans have been desperate for an imaginative mind to try something new around Lillard for years. Just like I’m attempting to try something new because your Lakers or Sixers or whatever jersey you can photoshop him into dream is a nightmare for Blazers fans, myself included.

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