The Blazers’ offseason looks hopeless. Here are some straws to grab hold of.

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

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

Lillard watched it all as he prepared to finish the Olympics. In Tokyo, he plays his usual excellent basketball and issues consistent, even reassuring statements: He says his future in Portland depends on how urgently Olshey improves the roster.

After a very quiet draft night for the Blazers last week, all eyes in Rip City are on the NBA free agency opening at 3 p.m. Monday. Any chance of fulfilling Lillard’s wishes will then begin.

The first domino: Norman Powell

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

But hanging on to Powell’s service may not be straightforward. He will be an unrestricted free agent and will therefore be able to sign with any team in the league. A franchise with a large margin, like the New York Knicks, can throw a massive offer to Powell if they hit big-name free agents.

As a team that plans to be far above the NBA salary cap threshold, if Powell leaves, Olshey will have no way of replacing 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 just can’t allow that to happen.

Of course, Powell and his agent will know this and likely make a tough deal. It can cost over $ 20 million a year to keep Norm.

Will Olshey finally swing for the fences?

Assuming Olshey convinces Powell to stay in Portland, his next consideration will be to rebalance the Blazers roster. Lillard, McCollum and Powell are all extremely talented on offense, but range from questionable to downright bad on defense. They are also all around 6 feet 3 inches tall. Even in 2021, it’s a woefully undersized trio against many teams.

Ideally, Olshey will build a mega-trade that trades McCollum and draft picks for a star-caliber player who better complements Powell and Lillard. Someone like Pascal Siakam from Toronto, Ben Simmons from Philadelphia or Domanatas Sabonis from Indiana, all three would be available for commercial offers. Jusuf Nurkic, who is in the final year of his current contract, could be used to sweeten the pot if a potential mega-trade emerges.

The catch: Astute Blazers fans are rolling their eyes right now. Fans, and even members of the media, have been pondering a McCollum trade for literally years, but Olshey has repeatedly said such a deal is not an option.

No full explanation has ever been offered for CJ’s trade resistance. Is Olshey reluctant to swap one of his “guys”? Does Lillard value McCollum so much as a teammate / friend that he pressured the front office to resist commercial offers? Or is McCollum simply lacking in significant business value as a one-dimensional marker?

Whatever the explanation, Lillard’s waning patience and alleged re-signing from Powell forces Olshey to take a more serious look at McCollum’s business possibilities.

Can the Blazers sign free agents?

After making decisions regarding Powell and McCollum, Olshey’s attention will turn to filling the team bench. Last year’s playoff rotation relied heavily on Enes Kanter, Carmelo Anthony and Afernee Simons as substitutes. These three make the Lillard / McCollum / Powell trio look like the 2000 Blazers in 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) Powell’s relaunch, they will be subject to, or very close to, the NBA luxury tax, and will only be able to recruit new players using the mid-level taxpayer exception. (TMLE) or a minimum wage contract. The $ 5.9million TMLE must be put to good use to attract a veteran who can immediately improve bench rotation and absorb heavy minutes when a titular 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.

Likewise, turning a minimum wage exception into a rotational player would be a huge boon to the Blazers’ chances. (Think Carmelo Anthony, but proficient in defense.)

Beyond that, the Blazers don’t have a lot of business 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 pack 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 non-competitor. He used that strategy to perfection last year, packing Trevor Ariza and draft picks to hook Robert Covington.

What is the most likely outcome?

Olshey doesn’t have an easy job this summer. Lillard, and all the fans in town, are tired of losing in the first round of the playoffs. Without dramatic improvements, Dame Time runs out by next summer.

Given Olshey’s past reluctance to trade McCollum, the most likely scenario is that the Blazers will re-sign Powell and then pray that the starting Lillard / McCollum / Powell / Covington / Nurkic roster is good enough to stay. with the league’s elite teams. Pushing your chips on these five is not a hopeless bet, but they’ll need help off the bench to even get a puncher’s chance to fight. After blocking the starters, Olshey must acquire multiple productive players with both the TMLE and a minimum contract, as well as trading a future first-round pick for immediate help.

Basically, fingers crossed that Olshey can replicate Enes Kanter and Rodney Hood’s glorious trade deadline acquisitions of 2019 and we don’t get stuck with another summer of pretending that Mario Hezonja and Pau Gasol will get the Blazers on the bump.

There is still a small ray of hope, but as Lillard’s bounty clock continues to tick, that hope keeps fading.

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