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The Milwaukee Bucks made one of the most shocking moves of the offseason when they waived and stretched Damian Lillard, less than a year after acquiring him. But what unfolded next turned out to be one of the more heartwarming moments of this NBA summer, a homecoming for the All-Star guard.
After being waived, Lillard became a free agent for the first time in his career. And despite the swirling rumours of potential new suitors, he had already made one thing clear: his rehab from an Achilles injury would happen in Portland, the city where he spent 11 years and built both his legacy and his life.
So when the news broke that Lillard would be rejoining the Portland Trail Blazers, it wasn’t entirely a surprise, but it was deeply meaningful. And, according to Lillard himself, a familiar face may have nudged the decision along.
Speaking in a recent interview, Lillard revealed that the first message he received after being waived was from none other than Jrue Holiday, his former Bucks teammate and 2021 NBA Champion.
“As soon as I was waived, and obviously he knows that I live here and built my home here and stuff, so he just sent me the eyeball emoji,” Lillard said with a smile. “And I kinda knew already. I already knew where I was pivoting to when he sent it, but I just didn’t wanna say nothing too soon.”
Holiday, who recently landed in Portland following a stint in Boston (where he won another title in 2024), may have unintentionally, or very intentionally, set the wheels in motion for a reunion between Lillard and the city that raised him.
It’s rare to see full-circle stories like this in the modern NBA. After a dramatic trade to Milwaukee in 2023, followed by an injury-shortened season and his eventual release, Lillard’s return to Portland feels like more than just a basketball move, it’s a personal and emotional one.
While he won’t be competing on the court this upcoming season due to his Achilles rehab, his presence will be felt in the Trail Blazers organisation, the city, and the locker room. Portland now has both Holiday and Lillard, two respected veterans and champions, in their ranks, even if only one is expected to suit up in the short term.
It’s unclear what Lillard’s long-term playing future looks like. But for now, the return to Portland offers closure, comfort, and a connection to home. and maybe, just maybe, a spark of something new down the road.