Damian Lillard Had Funny Issue With Jrue Holiday During Time With Bucks

Lillard detailed the funny issue he had with Holiday while he played for the Bucks.

Former Milwaukee Bucks guard Damian Lillard (0) drives for the basket against former Boston Celtics guard Jrue Holiday. / Benny Sieu-Imagn Images

With Damian Lillard returning to the Portland Trail Blazers over the weekend on a three-year deal, he will team up for the first time with guard Jrue Holiday, who was traded from the Boston Celtics to the Trail Blazers earlier this month.

Lillard and Holiday's names have been tied together since the Trail Blazers sent Lillard to the Milwaukee Bucks for Holiday in 2023. Holiday was then traded to the Celtics days later. Though this will be Lillard and Holiday's first time on the same team, they previously developed their relationship after that trade because Lillard rented out Holiday's house in Milwaukee during his time with the Bucks.

Lillard recalled Wednesday that were was one major issue as he rented out Holiday's house—his WiFi was not great. The two players talked a lot in large part so Lillard could complain to Holiday regarding the WiFi.

"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."

Damian Lillard on his relationship with Jrue Holiday 😂😂

"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… pic.twitter.com/42mpBv5tzr

— Brenna Greene (@BrennaGreene_) July 23, 2025

Lillard will be taking on more of a mentor—or assistant coach—type role this season as he recovers from a torn Achilles, but he is finally teammates with Holiday and the two should get to play alongside each other in 2026–27.

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