Damian Lillard’s Hilarious Encounter With Jrue Holiday on the Bucks Goes Viral!

Over the recent weekend, Damian Lillard has re-signed with the Portland Trail Blazers for a three-year term, marking his first collaboration with guard Jrue Holiday, who recently joined the team from the Boston Celtics.

The paths of Lillard and Holiday crossed when the Trail Blazers traded Lillard to the Milwaukee Bucks in exchange for Holiday in 2023. Shortly after, Holiday moved to the Celtics. Although this is the first time Lillard and Holiday are teammates, their relationship began earlier when Lillard stayed in Holiday’s Milwaukee residence during his stint with the Bucks.

Lillard shared with the media on Wednesday that a notable problem he faced while renting Holiday’s property was the subpar WiFi connection. This issue became a frequent topic of conversation between the two athletes.

“While I was living in Milwaukee, I rented his place for two years, so we ended up talking quite a bit. Mainly, I was always bringing up issues about the WiFi,” Lillard explained to journalists. “There’s even a video online where I’m greeting him at a game in Boston, and people were puzzled by our exchange. We were actually discussing his WiFi situation right then.”

This season, Lillard is expected to adopt a more advisory or assistant coach role as he recuperates from a torn Achilles. However, he is thrilled to finally be teaming up with Holiday, with expectations high for them to play together in the 2026–27 season.

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