1:37pm: The meeting will take place on Monday, tweets Chris Haynes of Bleacher Report and TNT. Lillard’s agent, Aaron Goodwin, will also be present.
8:51am: The Trail Blazers’ lottery luck and the addition of a strong rookie class weren’t enough to change Damian Lillard‘s mind about playing with a young team, sources tell Sam Amick of The Athletic.
General manager Joe Cronin said over the weekend that he’ll talk with Lillard once the star guard returns from a vacation in France (Twitter link from Danny Marang of 1080 The Fan in Portland). That meeting is expected to take place early this week, giving Lillard and the Blazers time to map out their future before the start of free agency on Friday.
Portland landed the No. 3 pick in this year’s lottery and was able to add a potential future star in Scoot Henderson. The Blazers also picked up Kris Murray at No. 23 and Rayan Rupert at No. 43, adding three more prospects to the collection of young talent already on hand.
However, it’s not the type of team that Lillard prefers as he nears his 33rd birthday next month. Lillard declared after the regular season ended that he wants Cronin to add some veterans who will help turn the Blazers into a contender, and he has repeated that stance in subsequent interviews.
Amick hears that Lillard’s dream scenario is to re-sign Jerami Grant and add Draymond Green in free agency. The Warriors are reportedly confident about their chances to keep Green, but Amick states that the size of his contract could still become an issue.
Amick also points out that the Blazers don’t currently have enough cap room to sign Green, who’s believed to be seeking a new deal with a starting salary in the $20MM range. A sign-and-trade could be possible, although Amick believes a third team would have to be involved to make the financial aspects work.
Amick mentions Raptors forwards Pascal Siakam and OG Anunoby as other possibilities, but he notes that Toronto has numerous teams that are interested in both players.
An important part of this week’s meeting will be for Lillard to gauge the front office’s commitment to upgrading the roster in time for next season, sources tell Amick. If he believes Cronin and owner Jody Allen are serious about building a contender, then he’ll hold off a decision about his future through at least the early part of free agency. If he’s not convinced, Lillard could decide to ask for a trade, possibly before free agency begins.
If that happens, Amick singles out the Heat as the main team to watch. Lillard has “serious interest” in going to Miami, sources tell Amick, and the Heat are believed to be equally interested in acquiring him.
Lillard’s desired destination will factor into any trade because of his years of service in Portland and the size of his contract, Amick adds. With four seasons left at $216MM, including a $63MM player option for 2026/27, Amick states that it’s hard to imagine any team trading for Lillard unless he wants to go there.