Damien Lillard surprised the NBA community by returning to the Portland Trail Blazers after the acquisition of the Milwaukee Bucks.
Lillard rejoined the Trail Blazers organization, rejoining overtures from big names such as the Los Angeles Lakers and Golden State Warriors.
Point Guard Homecoming creates interesting dynamics for Jrue Holiday, who was first traded to Portland on a 2023 contract that sent Lillard to the Bucks.
Portland regained vacation this summer after a championship run with the Boston Celtics. And some may expect tensions between the two security guards due to their trade history.
However, Lillard revealed that their relationship was positive and that personal connections extend beyond basketball.
Lillard rented a Milwaukee home on Holiday during the two years of Bucks, creating regular communication between them. Their conversations covered practical issues rather than basketball tension.
“When I lived in Milwaukee, I rented his house for two years. So I actually rented his house for the past two years. So we talked a lot.
The arrangements of life led to a common argument that observers misunderstood as basketball-related tensions.
Their on-court exchanges during the Boston-Milwaukee game sparked speculation about the circumstances of their relationship.
“It’s an online clip where I waved him. We played him in Boston, and we interacted, and what was the people like? And we were literally talking about his Wi-Fi in his house.”

Holiday reached out to discuss practical aspects of returning to Portland, including housing recommendations and organizational insights.
“So he reached out to those areas, things like that, things like that, and things like that, and a bit about the organization,” Lillard said.
Until the holidays, Lillard highlighted his connection with Portland 13 years later in the franchise. This connection also seems to have influenced his decision to return despite opportunities for better championships elsewhere.
“I love living in Portland. My family is in Portland. It’s where people come here, I’m from California and I’ve lived here for the last 13 years,” he explained.
Lillard’s current injury situation could delay the debut of the backcourt partnership. His recovery timeline determines when Portland can fully utilize both veteran security guards.
The Trail Blazers hope that veteran leadership can accelerate the development of young players while providing a playoff experience.
And the holiday championship pedigree with Boston adds credibility to their reconstruction efforts.
Their relationship foundation suggests potential chemical benefits when both players return to full health.
Personal connections established during Lillard’s Milwaukee tenure could lead to on-court success.