Damian Lillard has scheduled a meeting with the Portland Trail Blazers alongside his agent as his future at the team remains shrouded in doubt.
After Miami Heat speculation and rumours of being disappointed in how the Trail Blazers 2023 Draft played out, Lillard could see an exit from the franchise that selected the point guard 6th overall in the 2012 NBA Draft. Lillard has spent his entire 11-year NBA career in Portland but has long been rumoured to leave if the organisation doesn't emphasise winning.
According to Bleacher Report, Lillard is scheduled to meet with the Trail Blazers alongside his agent Aaron Goodwin. The context of the meeting is said to revolve around the team's immediate direction moving forward, which is not strange regarding his history with the organization.
Lillard's representation was reportedly unhappy with how Portland utilised the No. 3 pick in the NBA Draft after the team took Scoot Henderson, one of the highest-rated point guards on the big draft board, from the G League Ignite. Before the draft occurred, reports flourished of the team possibly using their draft pick and part of a trade involving Lillard that would have potentially paired the All-Start point guard with Mikel Bridges as a member of the Brooklyn Nets
The trade never happened, causing further speculation on the team's plans with Lillard after drafting Henderson. The Trail Blazers also selected power forward Kris Murray with pick 23, and shooting guard Rayan Rupert with pick 43.
In 2021, Lillard was in similar negotiations with the franchise, even meeting with LeBron James and Anthony Davis of the Los Angeles Lakers as he weighed his options prior to re-signing with the team after they promised him a more immediate championship push over the idea of a rebuild.
On a recent appearance on Showtime's The Last Stand podcast, Lillard spoke about moving to a different team after being asked by the media. When asked about the Nets, Boston Celtics, New York Knicks, and Miami Hear, Lillard listed the Heat and Nets as two teams with capable rosters - despite never saying that he wants to be traded.
“Miami, obviously,” said Lillard on ShowTime’s The Last Stand podcast on June 7. “Bam [Adebayo] is my dog for real, but Miami is an obvious one. Brooklyn is another obvious one because Mikal Bridges is my dog too. Both of them have capable rosters."
The Blazers and Lillard have maintained a special relationship over the past decade, showing loyalty to each other in a cut-throat league that has seen players find out they were traded on social media. However, as Lillard ages and the team struggles, philosophies for both entities have seemingly drifted apart.
Blazers GM Joe Cronin has remained firm in his stance that the Blazers will continue to try to win - especially regarding putting the necessary pieces around Lillard to do so. On the other hand, Lillard has made it clear that he doesn't want to stick around for a rebuilding process - especially after the team promised to get him more help at the end of last year.
Lillard is under contract with Portland until 2028, with a player option in the last year of his deal through 2027. If Lillard reveals that he wants to be traded during the meeting, the team will have to find suitors willing to attain the aging guard - or risk him declining his player option, making him an unrestricted free agent, free to go where he wants.