National Basketball Association

Portland Trail Blazers, franchise cornerstone Damian Lillard facing futures in flux

Updated Dec. 8, 2021 1:42 p.m. ET

By Ric Bucher
FOX Sports NBA Analyst

Damian Lillard, the Portland Trail Blazers’ incumbent star, is naturally one of the attractions for anyone interested in being the team's next president.

He also poses one of the biggest challenges, according to several NBA executives.

"If there are negatives to the job, one of them," an executive explained, "is what to do with Dame."

How could dealing with a six-time All-Star, model citizen and natural leader — who has declined overtures to go elsewhere and, instead, pledged allegiance to the Blazers — be anything other than a blessing?

Because it’s not the what –– it’s the hows with Lillard.

As in, how old he is: 31. How much he has remaining on his existing contract: three years, $135 million. And, now, how much he allegedly wants to sustain that pledge: This summer, he becomes eligible for a two-year, $107 million extension.

In essence, Lillard is saying to the franchise: I pledged allegiance to you. Now I want you to pledge allegiance to me. The problem? Shifting allegiances within the organization make that far from a foregone conclusion.

Gone is the GM who drafted Lillard in 2012, Neil Olshey, who was ousted last week for allegedly presiding over a toxic work environment. Olshey was committed to finding complementary pieces that kept Lillard as the undisputed star of the team.

Gone also is the owner, Paul Allen, who died in 2018. Allen had not only invested in Lillard as the team’s cornerstone but also supported his musical career and philanthropic interests.

The commitment of Olshey's and Allen's successors to Lillard is unclear. The direction that interim GM Joe Cronin will take the roster remains to be seen. Jody Allen, Paul’s sister, inherited the franchise upon his death. Her devotion to the Blazers as a whole, much less Lillard, is uncertain.

League executives — some formerly with the franchise, potential candidates for the job and happy-where-they-are rivals — all agree that the attraction of running the franchise is dulled by that first big hurdle: What to do with Dame?

"I love him," said the executive, citing the aforementioned attributes. "But he’s aging. Do you invest $50 million a year in him? He’s not John Wall, but it could be a John Wall situation. Or do you move him, and what does that look like? Those are big decisions."

Wall is currently wallowing in limbo with the Houston Rockets, an asset dying on the vine of a team that needed a six-game winning streak just to find company at the bottom of the Western Conference standings. Wall has not played since expressing his desire to be traded. Rockets GM Rafael Stone has been unable to find a team willing to take on his $44 million salary this season and the uncertainty surrounding his option to make another $47 million next season or enter free agency.

Damian Lillard and John Wall are in similar situations: accomplished yet aging players with expensive prices. (Photo by Alika Jenner/Getty Images)

It’s not a perfect comparison. Wall has had surgery on both knees and has recovered from a torn Achilles tendon. Lillard broke his foot in college but has not sustained any major injuries in his first nine NBA seasons. But he is also an undersized point guard who, despite the Allens’ financial largesse and Olshey’s constant tinkering with the roster, has never led the Blazers further than one Western Conference finals appearance. In that 2019 WCF, the Blazers were summarily swept by the Golden State Warriors.

Lillard is quite the hefty financial commitment even without the desired extension. Nor is the Lillard quandary the only one any prospective GM candidate has to consider. Another is the future ownership of the team: Paul Allen was a rabid basketball fan, heavily interested in the daily operation of the team and eager to finance a championship. Jody Allen has been as generous financially, but she never shared Paul’s passion for the sport and has done nothing to squash rumors that she intends to sell the franchise.

Then there’s the market: Portland is a small town that is wet and gray for a good part of the basketball season.

"For a young, single guy interested in night life, it’s one of the last places you’d sign up for," an Eastern Conference GM said. "It’s for the guy who is more interested in being a pro player, starting a family and sees the benefits Portland provides along those lines."

On the flip side, the Blazers are one of only two major professional franchises in the state — the other being MLS’ Portland Timbers — and they have engendered a passionate fan base and massive footprint within the community.

"It’s top-three in the league in that regard," a former Blazers executive said. "You’re part of a really important entity in the community."

The burden, of course, is that both the fans and the local media expect a championship. Despite having experienced that euphoria only once, some 45 years ago, and having reached the Finals just two other times, most recently 30 years ago, the Portland community viewed the eight consecutive playoff appearances under Olshey’s command as underachieving.

In any case, indications are that the Blazers are going to be deliberate in their search for Olshey’s permanent successor. The problem is that the team is staring down the barrel of a lost season and the end of that playoff streak — and small-market teams that slip into the lottery don’t always climb out of it all that quickly. Just ask the fans and media in Sacramento or Charlotte or New Orleans.

The Blazers are 11-14, currently living on the fringe of the play-in tournament. The reviews from other teams of first-year coach Chauncey Billups have been mixed. The Blazers got off to a slow start even before Lillard suffered an abdominal injury that has caused him to miss the past four games, three of them losses.

"The franchise is not clearly at the end of a run nor at the beginning of a rebuilding," the former Blazers executive said. "They need to do something. They need a change."

There have been unsubstantiated reports that Lillard wants the team to trade for Ben Simmons, the Philadelphia 76ers’ exiled young star. Accomplishing that would appear unlikely, even if Cronin is more than just a placeholder and has the authority to swing deals. First, reports out of Philadelphia are that team president Daryl Morey would want no less than Lillard in exchange for Simmons. Second, the Blazers’ second-best trade chip, CJ McCollum, was just diagnosed with a collapsed lung and is out indefinitely.

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Ben Simmons liked an Instagram post that referenced his potential pairing with Damian Lillard, but Skip Bayless says they wouldn't mesh.

That leaves center Jusuf Nurkic — in the final year of a four-year, $48 million deal — as the only worthwhile trade chip. But he makes no sense for the 76ers, who already have two established centers in Joel Embiid and Andre Drummond. Nurkic’s overall market value is undermined by both his pending free agency and his injury history. His past three seasons have been cut short by everything from a compound lower leg fracture to a broken wrist.

Olshey’s departure was preceded in late November by the resignation of Blazers’ CEO Chris McGowan, only adding to the sense of an organization in flux. But the franchise ledger still has more positives than negatives, according to prospective GMs. League sources say ownership paid Olshey more than $8 million a year, so finances are not a problem. Other positives include a home-court advantage that has produced a 10-4 record this season and a roster with only two players 30 or older.

One of them is Lillard. On which side of the ledger he belongs is all anyone interested in the GM job really wants to know.

Ric Bucher is an NBA writer for FOX Sports. He previously wrote for Bleacher Report, ESPN The Magazine and The Washington Post and has written two books, "Rebound," the story of NBA forward Brian Grant’s battle with young onset Parkinson’s, and "Yao: A Life In Two Worlds," the story of NBA center Yao Ming. He also has a daily podcast, "On The Ball with Ric Bucher." Follow him on Twitter @RicBucher.