Quick and simple question:
When do we know that it's time to start rooting for lottery position instead of wins? Is there a formula for how far under .500 you have to be before losses shift from "Darn, I wanted to beat them" to "Well, that's a 0.05% improvement in our odds to draft somebody good?"
Quick and simple answer: with the team as it stands, never.
I can give you 112,000,000 reasons why, too. Next year I’ll be able to give you 142,000,000. Only two teams are paying more salary than the Blazers this year: the Cleveland Cavaliers and the Los Angeles Clippers. One of those is World Champion, the other figures to go deep into the playoffs. If you pay for a Rolls Royce and get a Ghost instead of a Phantom, you’ll live with that. If you pay for a Rolls Royce and get a Yugo, something’s going to break.
Neil Olshey has been brilliant with his recent high draft picks. The lottery would be Portland’s surest way to acquire talent. But that option closed the moment they wrote all those checks. Missing the playoffs would call Portland’s entire plan into question. Coach Stotts would take serious heat and the flames might lick as high as Olshey himself. Blame would cascade downwards too. Despite the obvious scoring prowess, people would start to question how good Portland’s core guards are. It’d be a nuclear-level event.
Speaking of that core, the Blazers have to protect it not just from external criticism but from internal doubt. Portland’s eggs rest securely in the basket of Damian Lillard and CJ McCollum. Absent a blockbuster trade, they’re committed to that duo in perpetuity. Goodwill from their stars is imperative. The franchise cannot give the impression of waffling with the roster as a whole or in their confidence in that backcourt. As soon as Dame and CJ lose faith, the whole experiment is going out the window and a complete rebuild is in the offing. Those long-term contracts look secure now but four years go by quickly, especially when you consider that free agency will all but force you to move them within three if they’re not certain to return.
Keep in mind also (this will make you cringe): Lillard is 26 years old and in his fifth NBA season. He’s not a youngster waiting for his prime years, he’s entering the cusp of them. When his current contract expires he’ll be 30. McCollum is behind him, of course, but not far. The Blazers dare not waste the fat part of this backcourt’s bell curve. They’re not close to that yet, but a trip to Lottery Land would not be a promising start.
Consider also that unless the Blazers hit a super-bonanza, a lottery pick would take 2-3 years to develop. Banking on a plan to save an era that would be half over before the plan even hits full stride doesn’t seem feasible.
That’s why everybody inside and outside the organization should be rooting for wins and wins alone right now. That’s the only thing that will make things better. Anything else outside of a major trade will be cold comfort.
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—Dave email@example.com / @Blazersedge / @DaveDeckard