The moment when Damian Lillard's return to the Portland Trail Blazers was conceived

The seeds for Damian Lillard’s return to the Portland Trail Blazers were planted during his first season with the Milwaukee Bucks, as detailed by ESPN’s Jamal Collier. His agent, Aaron Goodwin, and Portland's general manager, Joe Cronin, had a conversation in January 2024. During that meeting, they identified past communication breakdowns and agreed that there were no hard feelings between the parties.

Lillard had requested a trade to the Miami Heat in the summer of 2023. However, when the trade did not materialize in September, Goodwin informed the Blazers that Lillard would stay in Portland. Nonetheless, the management wanted to resolve the situation before the start of training camp and traded him to Milwaukee. "Mostly, it was misunderstandings and lack of communication," admitted Lillard. "Joe and I never talked about [a possible return]. We just let things be. I think that was the mistake."

Lillard had always envisioned finishing his career with the Blazers, even before being traded. The meeting came unexpectedly after suffering an Achilles tendon rupture during the previous playoffs. Milwaukee decided to waive him and apply the stretch provision, allowing the Bucks to make an ambitious addition in free agency: Myles Turner.

The moment the trade was finalized

Collier reports that the possibility of trading Lillard was already on the table in Milwaukee even before his injury. The Bucks' management was considering various strategies, and trading Lillard was seen as an extreme measure to find another star to accompany Giannis Antetokounmpo.

Lillard chose to return to Portland by signing a three-year contract for 42 million dollars after being waived. Cronin met with him at his Portland home to inquire about his physical and mental state during the rehabilitation. He also discussed the team's progress in the rebuilding process. At that time, Lillard expressed that he believed the Blazers were heading in the right direction. Shortly after, both parties reached an agreement.

Lillard is expected to spend the entire 2025/26 season recovering from the injury. His agent fully trusts his comeback. "It's Dame. I know Dame," stated Goodwin. "I know his desire, his fight, how hard he works. And I didn't see this as the end of his career. Rather, I think he could even extend it because he always gives his all, and his body needed a rest."

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