The Blazers’ Offseason Looks Hopeless. Here Are Some Straws to Grasp At.

Damian Lillard has made his intentions clear: Trail Blazers president of basketball operations Neil Olshey must find a way to improve the team’s roster. If Olshey fails, the franchise’s cornerstone player may begin packing his bags.

In case you’ve been hiding under a rock since the injured Denver Nuggets eliminated the Blazers in May, the offseason has been an escalating farce: The team fired coach Terry Stotts, hired Chauncey Billups as his replacement, endured fan outrage over Billups’ 1997 sexual-assault allegation, conducted an investigation to reassure fans, refused to take questions about the investigation, and fired the investigator for sharing porn on his Twitter account.

Lillard watched all of this as he prepared to complete in the Olympics. In Tokyo, he’s playing his usual terrific basketball, and issuing consistent if not reassuring statements: He says his future in Portland depends on the urgency with which Olshey improves the roster.

After a very quiet draft night for the Blazers last week, all eyes in Rip City turn toward the opening of NBA free agency at 3 pm on Monday. Any chance of satisfying Lillard’s wishes will kick off then.

The first domino: Norman Powell

Olshey’s first priority will be to re-sign free agent Norman Powell. The 6-foot-3 guard played a key role for the Blazers during the latter half of the season, averaging 17 points per game while shooting 36% on 3-pointers after being acquired from the Toronto Raptors in a trade-deadline deal.

But hanging on to Powell’s services may not be straightforward. He will be an unrestricted free agent and thus can sign with any team in the league. A franchise with significant cap room, like the New York Knicks, may throw a massive offer at Powell if it strikes out with the marquee free agents.

As a team that projects to be far over the NBA’s salary cap threshold, if Powell does walk away, Olshey will have no way to replace him with a player of a similar caliber. Powell was arguably the team’s third-best player, behind Lillard and CJ McCollum, so the talent-poor Blazers simply cannot allow that to happen.

Of course, Powell and his agent will know that and presumably drive a hard bargain. It may cost upwards of $20 million a year to keep Norm.

Will Olshey finally swing for the fences?

Assuming Olshey does convince Powell to stay in Portland, his next consideration will be rebalancing the Blazers’ roster. Lillard, McCollum and Powell are all extremely talented on offense but range from iffy to downright bad on defense. They’re also all about 6-foot-3. Even in 2021, that’s a woefully undersized trio against many teams.

Ideally, Olshey will construct a mega-trade that swaps McCollum and draft picks for an All-Star-caliber player who better complements Powell and Lillard. Someone like Toronto’s Pascal Siakam, Philadelphia’s Ben Simmons, or Indiana’s Domanatas Sabonis—all three are reportedly available for trade offers. Jusuf Nurkic, who is on the final year of his current contract, could be used to sweeten the pot if a potential mega-trade does emerge.

The catch: Astute Blazers fans are rolling their eyes right now. Fans, and even the media, have pondered a McCollum trade for literally years but Olshey has repeatedly stated that such a deal is off the table.

No comprehensive explanation has ever been offered for the CJ trade resistance. Is Olshey hesitant to trade one of “his guys”? Does Lillard value McCollum so much as a teammate and friend that he’s pressured the front office to resist trade offers? Or does McCollum simply lack significant trade value as a one-dimensional scorer?

Whatever the explanation, Lillard’s waning patience and the presumed re-signing of Powell forces Olshey to more seriously evaluate McCollum trade possibilities.

Can the Blazers sign any free agents?

After making decisions about Powell and McCollum, Olshey’s attention will turn to filling out the team’s bench. Last year’s playoff rotation leaned heavily on Enes Kanter, Carmelo Anthony, and Afernee Simons as backups. Those three make the Lillard-McCollum-Powell trio look like the 2000 Blazers on defense. Regardless of what happens with McCollum, Olshey must find more depth.

The catch is that the Blazers will have few options to acquire free agents. After (hopefully) reupping Powell, they will be into the NBA’s luxury tax, or very close to it, and will only be able to sign new players using the taxpayer midlevel exception or a minimum salary contract. The TMLE, worth $5.9 million, must be put to good use to lure a veteran who can immediately improve the bench rotation and absorb heavy minutes when a starting player is unavailable. Big men like Kelly Olynyk or Nerlens Noel, as well as fan favorites like Bobby Portis or Patty Mills, might catch Olshey’s attention.

Similarly, turning a minimum salary exception into a rotation player would be a huge boon for the Blazers’ chances. (Think Carmelo Anthony, but competent on defense.)

Beyond that, the Blazers do not have many trade assets outside of McCollum and Nurkic. If no blockbuster trade emerges, Olshey’s next best bet for immediate improvement via trade will likely be to package future first-round draft picks with a player who can serve as salary ballast (e.g., Derrick Jones Jr.) to grab an impact player from a noncontender. He employed this strategy to perfection last year, packaging Trevor Ariza and draft picks to snag Robert Covington.

What’s the most likely outcome?

Olshey does not have an easy job this summer. Lillard, and every fan in the city, is tired of losing in the first round of the playoffs. Without dramatic improvements, Dame Time runs out by next summer.

Given Olshey’s past hesitancy to trade McCollum, the most likely scenario is that the Blazers re-sign Powell and then pray that the Lillard-McCollum-Powell-Covington-Nurkic starting lineup is good enough to hang with the elite teams in the league. Pushing your chips in on those five isn’t a hopeless bet, but they’ll need bench help to have even a puncher’s chance at contending. After locking in the starters, Olshey must acquire multiple productive players with both the TMLE and a minimum contract, as well as by trading a future first-round pick for immediate help.

Basically, cross your fingers that Olshey can reproduce the glorious Enes Kanter and Rodney Hood trade deadline acquisitions of 2019 and that we don’t get stuck with another summer of pretending that Mario Hezonja and Pau Gasol will get the Blazers over the hump.

There is still a tiny glimmer of hope, but as the clock on Lillard’s prime keeps ticking, that hope keeps fading.