Damian Lillard surprised the NBA community by returning to the Portland Trail Blazers after his Milwaukee Bucks buyout.
Lillard rejected overtures from big names like the Los Angeles Lakers and Golden State Warriors to rejoin the Trail Blazers organization.
The point guard’s homecoming creates an interesting dynamic with Jrue Holiday, who was initially traded to Portland in the 2023 deal that sent Lillard to the Bucks.
Portland then reacquired Holiday this summer after his championship run with the Boston Celtics. And with their trade history, some might have expected tension between the two guards.
However, Lillard revealed that their relationship remained positive, with personal connections extending beyond basketball.
Lillard rented Holiday’s Milwaukee home during his two-year Bucks stint, creating regular communication between them. Their conversations covered practical matters rather than basketball tensions.
“Because when I lived in Milwaukee, I rented his house for two years. So I have actually been renting his house for the last two years. So we talked a lot. Like, I was complaining to him about the Wi-Fi,” Lillard explained.
The living arrangement led to mundane discussions that observers misinterpreted as basketball-related tension.
Their on-court interactions during Boston-Milwaukee games sparked speculation about their relationship status.
“Like, it’s a clip online of, like, I shake his hand. We played him in Boston, and we had an interaction, and people were like, what? And then we were literally talking about his Wi-Fi at his house,” Lillard clarified.

Holiday reached out to discuss practical aspects of returning to Portland, including housing recommendations and organizational insights.
“So, he reached out just about, like, areas, like, to live in and stuff like that. And, a little bit about the organization,” Lillard said.
To Holiday, Lillard emphasized his connection to Portland after 13 years with the franchise. It seems like this connection also influenced his decision to return, despite potentially better championship opportunities elsewhere.
“I love living in Portland. My family is in Portland, and it’s a place where people come here to play, I was like, I’m from California, and I’ve been living here for the last thirteen years,” he explained.
Lillard’s current injury status may delay the backcourt partnership’s debut. His recovery timeline will determine when Portland can fully utilize both veteran guards together.
The Trail Blazers hope their veteran leadership can accelerate the development of younger players, while providing playoff experience.
And Holiday’s championship pedigree with Boston adds credibility to their rebuilding efforts.
Their relationship foundation suggests potential chemistry advantages when both players return to full health.
The personal connection established during Lillard’s Milwaukee tenure could translate to on-court success.