Damian Lillard is currently under contract through the 2024-25 with the Trail Blazers. That tenure could extend through the 2026-27 season if Lillard and the Blazers agree to a lucrative two-year extension in the 2022 offseason. According to ESPN’s Adrian Wojnarowski, that looming negotiation sits at the center of the Blazers’ search to replace recently-fired President of Basketball Operations Neil Olshey.
On Tuesday, Wojnarowski explained that Lillard’s drive for an extension has added friction to the Blazers’ operations.
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 2024-2025 to pay him $51 million at 35 years old and $55 million at 36 years old threatens to turn an asset of a contract into an albatross.
Wojnarowski went on to detail how the current field for Olshey’s former post is shaping up. According to the report from ESPN, several executives have voiced concerns about how Lillard’s potential extension could impact the Blazers’ future.
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.
Wojnarowski capped off his insight into prospective extension talks between the two parties by detailing the rumored lengths that Lillard’s camp is going to in order to sell the Blazers on the idea.
Now, Lillard’s group is privately selling the idea of trading his veteran teammates with value and rebuilding around him — on that extension. Some candidates initially believed that Lillard’s reps would have input with ownership on the next GM, but that has faded quickly. Rival GMs knew they had to deal directly with Olshey to get deals done with the Blazers, that he had full autonomy to make decisions. Those seeking Olshey’s old job believe they need to sell themselves to ownership, not to those surrounding the star player.
Lillard, who is currently out of the lineup with a lingering abdominal injury, has appeared in 20 games this season.
You can read the full report from Wojnarowski at ESPN+ (subscription required).