ESPN's Adrian Wojnarowski reported Tuesday that at least three teams won't reach out to the Blazers about a trade until the six-time All-Star makes a formal demand:
"If Lillard asks out, they know the Blazers will lose some leverage in the asking price—and are waiting on it. Philadelphia made an offer, but New York never did, league sources said. Lillard's reps offered mixed messages on the star's intentions to stay or go, and rival teams say that the star's camp had real concerns about [former general manager Neil] Olshey's willingness to recommend the extension to ownership in 2022."
Lillard is signed through the 2024-25 season, and his four-year, $176.3 extension kicks in this year. An exit from Portland is beginning to feel more and more likely, though.
The Blazers have failed to get out of the first round of the NBA playoffs in four of the last five years, and hiring Chauncey Billups as head coach hasn't changed the franchise's direction. In fact, making the postseason could be a challenge as Portland sits 10th in the Western Conference at 11-14.
As if the on-court difficulties aren't enough to make Lillard question his long-term future in Portland, the Blazers are in the process of finding a replacement for Olshey, whom the organization fired following an investigation into workplace culture.
According to The Athletic's Sam Amick and Shams Charania, Lillard isn't signaling to the front office that he wants to leave now, but he laid out some issues he'd like to see addressed:
"Lillard intends to give the Trail Blazers organization time to find its next leader of basketball operations. But beyond the front office component, the face of the franchise still wants significant changes to the roster. Multiple sources have told The Athletic that Lillard would like to play with Philadelphia 76ers three-time All-Star Ben Simmons. The Trail Blazers’ league-worst defense would instantly improve, and sharing a backcourt with a non-shooter could work given Lillard's high-volume usage."
For now, Joe Cronin is working as the interim general manager, and Wojnarowski reported the search for Olshey's permanent replacement is complicated by Lillard's desire to sign a two-year, $107 million extension on top of his current deal:
"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."
For aspiring GMs, trading Lillard and kicking off a rebuild might be preferable to making short-term moves for a roster that might have reached its ceiling. The Blazers don't have the trade assets to land another marquee star, and acquiring Simmons may not move the needle based on his disastrous playoff showing last year.
Not surprisingly, other NBA teams appear to be smelling blood in the water.
Especially if they miss the postseason, the Blazers could see a lot of their bargaining power at the negotiating table evaporate.