The NBA trade between Damian Lillard and Jrue Holiday last year involved more than just swapping teams—it included exchanging homes as well. Lillard recently revealed in an interview that he spent two years renting Holiday’s house in Milwaukee, which led to casual conversations, including complaints about the Wi-Fi. This unusual personal twist came alongside the professional challenges each guard faced during the transition.
How Lillard Endured Milwaukee Life and Connected With Holiday
When Damian Lillard moved to Milwaukee, he stepped into the home Jrue Holiday had previously occupied. Despite the house’s less-than-ideal Wi-Fi connection, Lillard made the most of the situation and stayed in frequent contact with Holiday.
“When I lived in Milwaukee, I rented his house for two years, so we talked a lot,”
Lillard shared.
“Like, I was complaining to him about the wifi. There’s a clip online of me shaking his hand when we played them in Boston. We had an interaction, and we were literally talking about his WiFi at his house.”
This candid exchange highlights the human side of what is often viewed as a purely professional trade. The two guards found common ground through shared experiences both on and off the court. Lillard’s adjustment challenges were compounded by his family remaining in Portland and difficulties settling into a new environment.
Life Advice From Lillard to Holiday After Their Team Swap
After Jrue Holiday was traded to Portland, the dynamic between the two veterans shifted, with Lillard offering guidance on life in Oregon. He advised Holiday on neighborhood choices, the local culture, and how to handle Portland’s famously rainy weather.
“He reached out just about like areas to live in and stuff like that, and a little bit about the organization,”
Lillard explained.
“I told him, like, I live in Portland, my family’s in Portland. When people come here to play, it’s usually raining, they’re only in town for a night, and it’s just grey skies. But I’m from California and I’ve been living here for the last 13 years. I think once you get here and you get on the ground, you learn to like it, or love it, in my case.”
This advice reflects Lillard’s deep connection to Portland, where he has cultivated a life beyond basketball and adjusted to its unique climate. Holiday, meanwhile, was stepping into a new role in a city that might have felt foreign at first but offered familiar court opportunities alongside his new teammate.
Comparing the Bucks Experiences of Lillard and Holiday
Jrue Holiday’s time with the Milwaukee Bucks had its high points, including winning the NBA title in 2021. In contrast, Lillard’s tenure there was marked by struggles both on and off the court. He faced difficulties adapting, especially as his family remained in Portland, and his stats reflected inconsistency, with a 24.6 points, 4.5 rebounds, and 7.0 assists per game average on 43.8% shooting during his 2023-2025 stint. The Bucks themselves encountered tough competition, which further complicated Lillard’s impact on the team.
Ultimately, this summer saw Lillard returning to the Trail Blazers after being waived by Milwaukee, a move widely regarded as beneficial for his career. Returning to Portland grants him proximity to family and better conditions for recovery while still allowing him to earn a significant salary.
Jrue Holiday’s New Chapter with the Trail Blazers
Even though Portland was not Jrue Holiday’s initial preference this offseason, his role with the Trail Blazers is expected to be substantial next season. As Lillard focuses on his recovery, Holiday’s presence will help solidify the team’s backcourt. Their past personal exchanges and mutual respect position both guards to thrive in Portland’s environment.
The Trade as a Full-Circle Situation for Two Veterans
What began as a high-pressure roster exchange has evolved into a shared journey marked by understanding and camaraderie. Although neither Damian Lillard nor Jrue Holiday likely anticipated the exact path ahead, both have navigated the transition respectfully, punctuated by lighthearted Wi-Fi banter. Now reunited in familiar surroundings, these veteran guards have the opportunity to chase success with a deeper appreciation of the challenges they overcame.
Our Reader’s Queries
Q. Why does Jrue Holiday wear 4?
A. According to Gary Washburn from the Boston Globe, Holiday shared on Thursday that he picked the number because he has three siblings. Before deciding, he contacted Isaiah Thomas, a former Boston player who wore the same number and was once an MVP finalist.
Q. Did Jrue Holiday have a ring?
A. In 2020, he was traded to the Milwaukee Bucks and helped them win an NBA championship in 2021. In 2023, the Portland Trail Blazers traded him to the Boston Celtics. He secured his second NBA championship with the Celtics in 2024. During the 2025 offseason, he was traded back to Portland.