The Portland Trail Blazers are in the market for a new top executive after an independent investigation led to Neil Olshey’s ouster last week. Whomever takes over will step into a situation with a superstar who has not been shy about his desire for the franchise to become more competitive, as Damian Lillard stressed on several occasions during the offseason.
That didn’t quite happen — Portland largely opted to run it back with its core players this season with a few changes in its rotation — and now, the team sits 11-14 and is holding onto the final spot in the Western Conference play-in tournament. Lillard hasn’t demanded a trade or anything like that, and according to a new report from Adrian Wojnarowski of ESPN, he’d actually like a contract extension this offseason, one that would pay him $107 million over two years. This, when tacked onto his current deal, would pay Lillard $51 million in 2025-26 and $55 million, the largest single-season sum in league history, the following year when he would be 36 years old.
According to Wojnarowski, this has actually developed into something that has led to a bit of trepidation among some folks who might be interested in taking the Blazers’ top executive job.
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.
This is the latest bit of news about Lillard’s future in Portland, as it was reported earlier this week that he’d like it if the team pulled off a trade for disgruntled Philadelphia 76ers standout Ben Simmons. Currently, Lillard is sidelined as he works his way back from an abdominal injury.
