Portland Trail Blazers chair Jody Allen told her team in "early September" it was time to "move on" from Damian Lillard, according to the Washington Post's Ben Golliver.
Lillard was dealt to the Milwaukee Bucks September 28.
The seven-time All-Star had requested a trade in July after 11 seasons with Blazers.
"We really need to move on," Allen said on a Zoom call prior to the trade, as recalled by Blazers president Dewayne Hankins. "We've got great young talent. We're not like other rebuilding teams who don't have a strong core of young players. It's time to turn the page."
Allen's talk led to the Blazers' decision to remove Lillard from team promotional materials, where he was replaced by with No. 3 pick Scoot Henderson and last season's breakout star Anfernee Simons, per Golliver.
Despite Lillard's public criticism of the Blazers, he was a frequent defender of Allen. Last summer, he challenged a report claiming Allen had refused to meet with him about his problems with the team. This summer, he took to Instagram live to clarify liking a negative social media post regarding Allen had been an accident.
Lillard also thanked Allen for her "support in some difficult situations away from basketball" in the goodbye letter he posted the day after being traded.
"Jody, the first time I met you, you had on a pair of Alexander McQueen sneakers and a vintage Blazers jacket, and I thought to myself, this is a cool woman," Lillard wrote. "I knew we would be alright. I apologize for any misunderstanding this summer because you have truly been great about everything the last five years."
Despite the positive relationship between Allen and Lillard, it was apparently clear to Allen Lillard wasn't going to be part of the Blazers' future.
According to The Athletic's Shams Charania and Sam Amick, Lillard had told the Blazers he was willing to participate in the start of the season to facilitate a trade with his preferred destination of the Miami Heat, but general manager Joe Cronin was skeptical. Blazers management wanted to remove "speculation and what they believed was a cloud over the organization" before the start of training camp, per Charania and Amick.
That was reportedly when Allen made the call for the team to begin distancing itself promotionally from Lillard. Given that he is now a Buck, it seems to have been the right choice.