As Damian Lillard makes his comeback to the Portland Trail Blazers on a three-year contract, he will join forces for the first time with guard Jrue Holiday, who was recently traded from the Boston Celtics to the Trail Blazers.
Lillard and Holiday’s names have been connected ever since the Trail Blazers traded Lillard to the Milwaukee Bucks for Holiday in 2023, with Holiday subsequently being sent to the Celtics just days later. Although this marks the first time Lillard and Holiday are on the same roster, they built their relationship after that trade because Lillard rented Holiday’s home in Milwaukee during his tenure with the Bucks.
Lillard remembered on Wednesday that there was one significant problem while he stayed at Holiday’s house—the WiFi was subpar. The two players communicated frequently, mainly so Lillard could voice his frustrations about the internet connection to Holiday.
Lillard mentioned to reporters, “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,”
“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.”
Dame on his relationship with new teammate Jrue Holiday 🙏
“I rented his house for two years [in Milwaukee]. I was complaining to him about the wifi.” 😂
(via @BrennaGreene_, @NBCSCeltics) https://t.co/Erdvo8RAtQ pic.twitter.com/kG45nuJqbc
— Bleacher Report (@BleacherReport) July 24, 2025
As he recovers from a torn Achilles, Lillard will assume a more mentor-like or assistant coach role this season, but he is finally teammates with Holiday, and they are expected to play together in the 2026–27 season.
