Per ESPN's Adrian Wojnarowski, Lillard's camp is "privately selling the idea of trading his veteran teammates with value and rebuilding around him" while selling team management on signing him to a two-year, $107 million extension when he's eligible to sign it in July.
Lillard's situation comes as the Blazers are in the process of starting their search for a new general manager. They fired Neil Olshey on Dec. 3 following an independent investigation into allegations that he created a toxic work environment by bullying and intimidating staffers.
According to Wojnarowski, Portland's search for Olshey's replacement "will soon be underway" with the team still deciding whether or not it will hire a search firm to recommend potential candidates.
"The Blazers will be wise to expect every candidate to come armed with two important questions: What are owner Jody Allen's plans to keep or sell the team? And more immediately, would a new GM have autonomy to rebuild the franchise not around but without Lillard," Wojnarowski wrote.
The idea of giving Lillard an extension averaging $53.5 million per year through the 2026-27 season when he will be 36 years old hasn't generated any enthusiasm from "several top-level GM candidates who fit the profile of Portland's applicant pool," per Wojnarowski.
There was speculation throughout the offseason about whether or not Lillard would request a trade from the Trail Blazers. He shut down those rumors in October while speaking to Jason Quick of The Athletic.
"Everybody is saying what they think I'm thinking, and what they think I'm going to do, but like, I'm not leaving Portland, you know?" he said.
Wojnarowski noted that Lillard "had no leverage to choose his next team over this past summer" because the 31-year-old is in his first season of a four-year, $176.3 million extension he originally signed in July 2019.
Amid an 11-14 start to the season, the Blazers appear to have reached a tipping point. Shams Charania and Sam Amick of The Athletic reported on Monday that Lillard "would like to play" with Ben Simmons.
There's no indication at this point that Portland and the Philadelphia 76ers are discussing a deal for Simmons. Wojnarowski noted three teams interested in Lillard "are waiting on him to make an offseason trade demand before calling Portland."
Lillard is currently out of action with an abdominal injury he has been dealing with since playing for Team USA in the Summer Olympics. The six-time All-Star is averaging 21.5 points per game, but he's shooting a career-low 39.7 percent from the field in 20 starts this season.