Neil Olshey Finally Opened The Second Envelope

The day after Portland’s unceremonious first-round exit at the hands of the Denver Nuggets, the Trail Blazers cut ties with long-time head coach Terry Stotts. But Portland’s now-former head coach plays a secondary role in the larger picture. The real story is about the management that remains in place.

As the Blazers’ President of Basketball Operations, Neil Olshey’s actions are reminiscent of an old business joke/fable, explaining how management can bluff their way through problems that might otherwise be pinned on them. Olshey, who earned a bachelor’s degree in English, probably never learned it in school but has almost surely heard it in the field.

There are many variations, but the story typically begins with something like this:

A new CEO has been hired to run a struggling business. And great news! People are excited and upbeat about the long-overdue exit of the current CEO, sending the stock price skyrocketing with high expectations.

Meanwhile, on the way out the door, the previous CEO hands the new CEO three numbered envelopes with notes inside. “Save these for as long as possible, then open the next numbered envelope when you’re in a crisis, and do what’s written on the note.”

Envelope #1: “Blame Previous Management”

Like many upper-middle managers, Neil Olshey plays to his strengths:

1. Deflect blame.
2. Speak for ten minutes without making meaningful statements or taking any responsibility.

One of Olshey’s favorite deflections? Hint that other decision-makers are responsible for the precarious spot the Blazers are repeatedly stuck in. (He also likes to blame the media for not providing the narrative he’d prefer, but that’s another column.)

Paul Allen’s presence created a unique twist for Olshey to implement. He cheerfully told the media that Allen was willing to spend money, while sometimes also hinting at his hands-on micromanagement tendencies (such as this fun clip where Olshey wistfully explains how the late Allen would rewrite their draft plans during the event). But in the process, Olshey subtly absolved himself of future blame, by creating a “Choose Your Own Adventure” situation for the listener:

• Was a transaction successful? “Go to Page 12: Olshey helped Allen make the right decision!”
• Did the player perform below their contract expectations? “Go to Page 30: Olshey begrudgingly accepted Allen’s decision.”

By deflecting responsibility, Olshey can stay out of the fray and let fans argue about which interpretation is correct.

Amazingly, Olshey eventually seemed to realize that he could get away with blaming his own past management by simply not naming the responsible party for the current situation. This can be seen in a semi-infamous 2017 interview with Blazers Broadcasting’s Brooke Olzendam, where he blames the Mason Plumlee trade on “financial realities” due to past decisions, without acknowledging that he himself created those very “financial realities”. This is honestly a quite brilliant maneuver.

That imaginary first envelope was highly effective for Olshey. It became his meal ticket, and it has remained in his pocket for years. It’s probably folded, crinkled, and has eight years of smudges and stains from old takeout containers. He’s been happy to whip out the note, slap it on the table like a compulsive gambler’s last dollar in Las Vegas, and hammer that point home every time anyone voiced concerns. It was the gift that just kept giving.

Until the 2021 NBA Playoffs.

With the team’s owner in attendance for Game 5, every Trail Blazer not named “Damian” shot 1-14 in two overtimes, scoring just two points in a demoralizing loss. Sometimes you can just blame the coach and move on; this time, the players were in a position to succeed, but fell. The Blazers suffered a personnel failure at a pivotal moment. In that moment, Olshey may have been adjusting his tie, Rodney Dangerfield style. The team’s fourth-quarter collapse in Game 6 simply punctuated the failure.

Deflection and passed-blame can only work for so long. In this case, nine years. With eyes on the team’s construction and salary limitations due to “financial realities”, it was time to crack open the second envelope.

Envelope #2: “Reorganize”

Post-playoffs, the Trail Blazers implemented the only reorganization technique available: Rebuilding the coaching staff for the first time since 2012. Olshey doubled down during his exit-interview press conference, laying the Blazers’ deficiencies primarily at the feet of Stotts, promising that replacing the coaching staff will fix the problems, along with the annual roster churn.

But he may have waited too long. Management seem to be satisfied with his statements for now, but others, namely fans and media, had mixed reactions.

After nine years in control of Basketball Operations, all roads lead back to Olshey. Nobody else can be blamed anymore. The Blazers entered the playoffs in a great position, with a relatively healthy team composed of not just the coach Olshey hired, but also the players he acquired. And they couldn’t beat an opponent struggling with injuries.

If the 2021 offseason changes don’t lead to success, Olshey is in a pickle. Unlike envelope #1, envelope #2 is rarely reusable for a General Manager. Sooner or later, he’ll have to open envelope #3.

Envelope #3: “Prepare Three Envelopes...”

With Stotts’ departure, Neil Olshey has publicly tied his fate to the satisfaction of Damian Lillard. And Lillard must know the power that grants: His coaching demand was quickly released by Chris Haynes, then later mitigated via both Haynes and Sam Amick once it went sour. Former Blazers beat reporter Jabari Young hinted that Lillard may be waiting, watching the Blazers’ summer activities before deciding his future. And earlier in the season, Haynes already expressed Lillard’s dissatisfaction. Control of the narrative seems to be paramount to Olshey, and he lost it at a key moment. We may see that Rodney Dangerfield move with his tie again.

Portland’s timeline places Olshey in a precarious position. Even though Lillard is at his peak, he turns 31 in the summer of 2021. Modern athletes typically age gracefully, but that ticking clock still brings a risk of injury or increased unhappiness. Can Olshey afford to say no to Lillard’s requests? If a dissatisfied Lillard decides to leave, Olshey will almost certainly need to crack open that third envelope.