Damian Lillard returned to the Portland Trail Blazers on a three-year contract this past weekend, reuniting with guard Jrue Holiday for the first time as teammates. Lillard and Holiday’s names have been linked ever since the Trail Blazers traded Lillard to the Milwaukee Bucks for Holiday in 2023, a move followed soon after by Holiday’s trade to the Boston Celtics. Though this season will mark their initial collaboration on Portland’s roster, their connection has grown off the court, particularly during Lillard’s stay in Milwaukee.
Lillard’s Experience Renting Holiday’s Milwaukee Home Included a Surprising Challenge
During his time with the Bucks, Lillard rented Jrue Holiday’s house in Milwaukee, which led to frequent conversations between the two players. Lillard recently shared that the biggest frustration he faced while living there was the poor WiFi connection. The internet issue became a running joke and a common topic in their talks, highlighting a unique side of their relationship beyond basketball.
“When I lived in Milwaukee, I rented his house for two years so we talked a lot. Like, I was complaining to him about the WiFi,”
Lillard told reporters.
“There’s a clip online of like I shake his hand, we played them in Boston, we had an interaction and people were like ‘What?’ And we were literally talking about his WiFi at his house.”
This candid moment shows how their off-court camaraderie helped maintain their bond despite being on different teams. The exchange about poor internet during games reflects a more personal and lighthearted aspect of their friendship in contrast to the intense nature of professional sports.
Lillard’s New Role on the Trail Blazers and Future Collaboration with Holiday
As Lillard begins this season recovering from a torn Achilles, his role will shift more toward mentorship and mentorship-like duties, with limited court time expected. Despite this, he and Holiday will officially share a team for the first time, paving the way for them to play alongside each other in the 2026–27 season. This development underscores a full-circle moment for both players after their trade history and time apart.
Their renewed partnership could provide the Trail Blazers with a seasoned backcourt dynamic, combining Lillard’s veteran leadership and Holiday’s defensive prowess as the team rebuilds. Fans and analysts alike will be watching closely to see how their relationship evolves on and off the court moving forward.
Our Reader’s Queries
Q. Why does Jrue Holiday wear 4?
A. According to Gary Washburn from the Boston Globe, Holiday shared during Thursday’s practice that his decision was influenced by having three siblings. Before deciding on the number, he spoke with Isaiah Thomas, a former Boston player known for wearing that same number.
Q. Did Jrue Holiday have a ring?
A. He was traded to the Milwaukee Bucks in 2020 and won his initial NBA championship with them in 2021. In 2023, Holiday moved to the Boston Celtics from the Portland Trail Blazers and earned another NBA championship in 2024. He was then traded back to Portland during the 2025 offseason.