To be fair to Neil Olshey, it's not like the Trail Blazers have readily available paths to the type of major roster upgrades that could vault them to legitimate championship contention.
If he could push a magic button to consummate a blockbuster trade for a star or sign a max-level player in free agency, it's safe to say Olshey would have done it even before Damian Lillard voiced his mandate for change on Friday.
At least some portion of Olshey's wide-eyed confidence in Portland's roster status quo is based in realities of its wholesale lack of flexibility. Not only are the Blazers a team full of pricey veterans poised to pick toward the end of the first round as long as Lillard is in town, but they're poised to butt up against the salary cap in 2021-22 even before addressing their biggest free agency domino.
Assuming Derrick Jones Jr. picks up his player option and Portland fully guarantees the final year of Jusuf Nurkic's contract, the Blazers will have $112.5 in committed money—a hair above the salary cap—next season for just eight players. That's no surprise to Olshey.
He's the one who inked Lillard and C.J. McCollum to massive, tandem extensions in the afterglow of Portland's trip to the 2019 Western Conference Finals, and he's the one who dealt Gary Trent Jr. for Norman Powell at the trade deadline despite the Blazers only possessing team control over the former.
Portland will be powerless to stop Powell, an unrestricted free agent, from signing with another team come August 2. The only advantages the Blazers have over competing suitors for Powell are Bird Rights carrots of a five-year contract and maximum annual raises of eight percent of his previous salary. Teams hoping to lure Powell with cap space can only give him up to a four-year deal with five percent annual raises.
Maybe Portland's ability to exceed any contract extended to Powell will lead to him re-signing in Rip City despite some tempting offers elsewhere. It better. Powell's free agency was always going to be the Blazers' most important matter of business this summer, but Lillard's demand for change only adds to the weight of its significance.
If Powell walks in August, perhaps for a bigger role with the New York Knicks or more organizational stability with the San Antonio Spurs, cash-strapped Portland will have no means of replacing his salary slot. Bird Rights allow the Blazers to re-sign Powell irrespective of the salary cap, a luxury they don't have with free agents from other teams.
Obviously, Portland is in no financial or existential position to withstand the loss of a player earning quality-starter money. The Blazers will need every team-building tool at their disposal—plus some heretofore dormant initiative and ingenuity from Olshey—to even come close to putting a revamped, title-worthy supporting cast around Lillard.
He made clear on Friday what Portland's failure to do so will mean for his future, Lillard's longing to bring a title to Rip City be damned.
Say what you will about Powell's two-way limitations and whether he's worth an $18-20 million annual contract in a vacuum. He's average at best on defense, with lagging positional versatility and a penchant for falling asleep away from the ball. As much as Powell's improved as a shooter since entering the league, his straight-line attacks in the halfcourt and overall prowess in transition could wane as his athleticism fades.
In an ideal world, would the Blazers want to give Powell, 28, a four-year deal at the high end of his market value? Probably not, but the constraints of Olshey's prior spending and composition of the incumbent roster means they must. Portland has no other option.
At least that's a far better proposition than the alternative, though. If Powell leaves in free agency, it'll be a flashing red light for Lillard's departure—whether via an imminent trade demand or one more season with the Blazers bound to end in postseason disappointment.