Question facing Portland owner, new GM: Extend Lillard or trade him?

Boston Celtics v Portland Trail Blazers
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While other GMs circled like a shiver of sharks, smelling blood in the water, Damian Lillard chose not to push for a trade out of Portland last offseason and give new coach Chauncey Billups a chance.

Since then Lillard has battled injury and the worst shooting slump of his career, Portland has gotten off to an unimpressive 11-14 start with the same terrible defense of years gone by, and general manager Neil Olshey was fired for violating the Trail Blazers’ “Code of Conduct.” In short, it has been a dumpster fire.

Now, as the search for the next Portland GM gets underway, the candidates for that position — and, more importantly, owner Jody Allen — face a tipping point with Lillard: Do they extend his contract this coming summer and make him the highest-paid player in the NBA, or is it time to trade him?

Adrian Wojnarowski of ESPN broke down the choice.

Lillard wants a two-year, $107 million extension in July, and he and his agent need the next general manager to sell ownership on the idea. As much as anything, this cuts to the core of the Blazers’ search process. His desire for an extension into his advanced NBA years has turned into a battle for the franchise’s future, an existential threat to reshaping and redirecting the organization in a post-playoff reality.

The prospects of Portland extending Lillard, 31, beyond his $48.8 million in 2024-25 to pay him $51 million at 35 years old and $55 million at 36 threatens to turn an asset of a contract into an albatross…

Among several top-level GM candidates who fit the profile of Portland’s applicant pool, there’s no enthusiasm to grant Lillard his massive extension contract through the 2026-27 season. In fact, several executives told ESPN they would be far more interested in the Blazers job with ownership’s blessing to move Lillard sooner than later.

Lillard himself questioned the sourcing and motivation of the story.

It’s still a valid question.

Lillard has been the face of the franchise and a loyal Trail Blazer his entire career, but he wants to win and get paid. Winning consistently at the highest level hasn’t happened and was not going to happen with this roster but Olshey couldn’t see it. He had a huge blind spot with his guy, CJ McCollum, and while Lillard may have wanted him traded for Ben Simmons — and may still want that — it was doubtful Olshey would ever have pulled that trigger.

Does a new GM want to come in, take on Lillard as he battles age in injuries, then try to trade McCollum and Jusuf Nurkic for players that can have this team contending around Dame? That is a huge ask. No doubt many GMs would prefer a tabula rasa, trade Lillard for young players and picks, and build something new (plus, that path gives a GM years of job security, nobody expects a rebuild overnight). Trading/moving on from a franchise icon like Lillard is not easy, and he can still play the game at a very high level when healthy — that kind of player is hard to replace.

What does Jody Allen want? She sits courtside in nearly every game, but she has been hands-off as an owner compared to her late brother. Absentee would be too strong a word for her ownership style, but it’s closer to that than active.

Since the death of Paul Allen there have been persistent questions about whether Jody would sell the team; as Wojnarowski notes any GM candidate worth their salt is going to ask Allen that directly. If she’s not selling — and there has been no indication she plans to — then what road does she want to go down with the roster? This is an ownership level call.

And it’s the big question facing Portland as it looks to retool its front office.