Damian Lillard Rented Jrue Holiday’s House, Then Gave Him Crucial Advice After Trade To Portland

NBA trades are usually all business, but for Damian Lillard and Jrue Holiday, last year’s blockbuster swap had a surprisingly personal twist. Not only did the two veteran guards switch teams, but they also swapped homes. During a recent interview, Lillard revealed that he had been renting Holiday’s house in Milwaukee and even had to complain to him about the Wi-Fi.

"When I lived in Milwaukee, I rented his house for two years, so we talked a lot," said Lillard. "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."

As Lillard was starting his tenure with the Bucks, he took over the space previously occupied by Jrue Holiday. It had terrible WiFi, adding yet another complication to Lillard's miserable transition. When Holiday was later traded to Portland, the roles reversed, and Lillard gave him advice on where to live, how to handle the city’s rain, and why he still calls it home 13 years later. 

“He reached out just about like areas to live in and stuff like that, and a little bit about the organization. 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."

Unlike Jrue Holiday, who won a title with the Bucks in 2021, Lillard's tenure in Milwaukee did not go nearly as smoothly. He struggled to adjust from the very start and struggled to settle in with his family still based in Portland. At the same time, his performance on the court was less than ideal (24.6 points, 4.5 rebounds, and 7.0 assists per game on 43.8% shooting from 2023-2025) as the Bucks struggled to keep up with their competitors.

This summer, Lillard finally returned to the Trail Blazers after being stretched and waived by the Bucks, and it was probably the best thing for his career. Not only does he get to rehab close to home, but he also gets to make a lot of money while doing it.

In the case of Jrue Holiday, it's no secret that the Blazers were not his first choice this summer, but he'll be playing a big role next season as Lillard continues his recovery. Now that he and Lillard are teammates, Jrue can get even more comfortable in Portland and learn to make the most of his new surroundings.

What started as a high-stakes roster swap has turned into a full-circle moment for two respected veterans. They may not have chosen this path, but Dame and Jrue have handled the transition with mutual respect and just enough friendly Wi-Fi slander to keep things light. Now, both are back in familiar roles, and for the first time in a while, they’ll get to chase wins with a shared understanding of what it took to get here.