Damian Lillard Narrates Hilarious Jrue Holiday Experience While With Milwaukee Bucks

Damian Lillard Narrates Hilarious Jrue Holiday Experience While With Milwaukee Bucks

Damian Lillard Narrates Hilarious Jrue Holiday Experience While With Milwaukee Bucks

Jrue Holiday, Damian Lillard (FS Image)

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When the Milwaukee Bucks traded Jrue Holiday away to acquire Damian Lillard via trade, many thought that they had found a perfect recipe to keep Giannis Antetokounmpo rooted to Wisconsin for the rest of his career. After all, Lillard is a scorer par excellence who has had some vintage playoff moments in his career. He would be, by far, the best supporting player that the Greek Freak had played with in Milwaukee.

However, things did not quite go to plan during Dame’s time in Milwaukee. The Blazers legend had a few fit issues before he got injured in his first season in Wisconsin. After Lillard’s injury and eventual recovery, he had to make do without Giannis in the first playoff bow he had with the Bucks after he was ruled out with injury in 2024. Finally, Damian Lillard himself tore his Achilles during the 2025 NBA playoffs and will be out for a year.

The much-vaunted duo was only able to win a single playoff game with both players on the floor. The Bucks decided to cut their losses and waive Lillard this offseason, stretching his $113 million salary out over five NBA seasons while attempting to get more help for Giannis.

Lillard never truly got the opportunity to settle down in Wisconsin. He didn’t uproot his family from Portland as his young kids had their lives around their school and other family members in Oregon. He rented Jrue Holiday’s mansion in Milwaukee and lived alone. And Damian Lillard had a specific complaint with the place owned by the Holidays as a tenant:

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 we’re like what? And we were literally talking about his wifi at his house.

Damian Lillard will have the opportunity to rewrite his legacy in Portland this time around

Damian Lillard’s return to Portland offers a chance to reshape his legacy with the Trail Blazers, where he spent 11 seasons building a reputation as a clutch performer and franchise cornerstone. Lillard’s departure left a bittersweet mark. Fans adored his loyalty and electrifying play, but the team never got close to a championship, with their deepest playoff run being the 2019 Western Conference Finals.

Damian Lillard
Damian Lillard (Imagn)

Damian Lillard can now redefine his narrative in Rip City. At 35, Lillard remains a prolific scorer, averaging 25.7 points per game in 2024-25 with Milwaukee, though his efficiency has slightly dipped (42.3% FG). Portland’s current roster, led by young talents like Scoot Henderson and Shaedon Sharpe, could benefit from Lillard’s veteran presence and playmaking.

His return symbolizes unfinished business as Lillard chases an elusive ring with the team that drafted him sixth overall in 2012. Beyond stats, Lillard’s legacy in Portland hinges on intangibles. His community impact, through philanthropy and loyalty during lean years, made him a beloved figure. Returning could mend any lingering fan resentment from his trade request, reinforcing his image as a player who values roots over ring-chasing. After all, Lillard’s brand has always been about loyalty, and he has a fresh chance to prove it.

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