Actually, he did it with Lillard in 2012 and it worked. He very specifically signed no PG would even kind of compete with Dame for minutes. All Olshey gave Stotts was Ronnie Price. I think it's one of the reasons Lillard is loyal to us. He knows he was gifted a career as a starting PG in this league and he doesn't forget it.
Olshey didn't sign any competent backup at all in Dame's rookie season after Indiana matched Hibbert's offer sheet. That was the worst bench in Blazer history, and one of the worst in NBA history. That was Olshey trying to cheapscrew something risk-free together and the next off-season, he added Mo Williams and replaced Hickson with Lopez. It was still a shitty bench, but at least Portland had a competent backup PG. And, IIRC Portland's record when Mo scored in double figures was even better than the 54 win pace they had that year
it’s also one of the main reasons Stotts has job security imo. I remember a couple years ago he mentioned how he stays out of Olsheys way and leaves all the roster construction up to him. That egomaniac would’ve fired Stotts awhile ago if he wasn’t so submissive. I’d say his loyalty (if you wanna call it that) to Neil is more significant than Dames loyalty to him.
Stotts and Olshey do not always agree on players or their playing time. Stotts isn't "submissive" to Neil, like you claim. Meyers is one example.
That’s because Neil doesn’t have any control over playing time, short of going over Stotts’ (or any other coaches) head, which would surely piss Dame off. He’s not dumb.
However, Olshey frequently constructs the roster to force Stott's hand on making sure he plays 'his guys'. Just last year Olshey only provided the following PF on the roster to start the year: Collins, Skal (currently out of the league), and Tolliver (out of the league). I guess you could possibly argue Mario (out of the league) and Little (rookie) were options - but I view both more as SF. If that doesn't scream "Play the guy I want you to", I don't know what does.
oh yeah, I definitely think he manipulates the roster. Even now, Stotts is essentially forced to play Simons because as bad as he’s been, he’s still the only real ballhandler they’ve got not named Dame. The only other option Terrys got is to run Dame into the ground.
The Blazers won't add a veteran as it would push them into the luxury tax. So the only option is a two way player or first doing a trade such as dumping Collins.