When the Milwaukee Bucks acquired Damian Lillard in a trade involving Jrue Holiday, fans anticipated that the move would help secure Giannis Antetokounmpo’s future in Wisconsin by pairing him with one of the league’s premier scorers. Lillard, known for his clutch playoff performances, was expected to be the best complementary player Giannis had ever had in Milwaukee.
However, Lillard’s time with the Bucks was marked by setbacks. Shortly after arriving, he experienced some physical issues before suffering an injury during his first season in Milwaukee. Giannis also missed the playoffs in 2024 due to injury, forcing Lillard to compete without his star teammate. Then, in the 2025 <a href="https://www.buzzineintl.com/category/basketball/nba/”>NBA playoffs, Lillard suffered a torn Achilles, sidelining him for an entire year.
As a result, their partnership yielded only one playoff victory with both players on the court. The Bucks opted to waive Lillard during the offseason, choosing to stretch his $113 million contract over five years to free up resources and pursue additional help to support Giannis.
Damian Lillard’s Unique Living Situation in Milwaukee
Lillard did not relocate his family from Portland during his Milwaukee stint, as his young children remained rooted in their Oregon community and schools. Instead, he rented the mansion previously owned by Jrue Holiday, living alone for two years in Milwaukee. This arrangement led to a humorous and unexpected complaint involving the house’s Wi-Fi.
“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, NBA Player
This amusing exchange took place during an interaction between the two players, highlighting an unusual aspect of Lillard’s experience off the court while living in Holiday’s home.
Returning to Portland Spurs Opportunities to Rebuild Legacy
Damian Lillard’s return to the Portland Trail Blazers presents a significant chance to reshape his legacy with the team that originally drafted him sixth overall in 2012. Over 11 seasons with Portland, Lillard has been known as a clutch scorer and franchise cornerstone, though a championship has eluded him. His deepest playoff advancement with the Blazers was the 2019 Western Conference Finals run.
During his one season in Milwaukee, Lillard maintained his scoring prowess, averaging 25.7 points per game in 2024-25, despite a dip in shooting efficiency to 42.3 percent. Portland’s roster, now featuring young talents like Scoot Henderson and Shaedon Sharpe, stands to benefit from Lillard’s veteran leadership and playmaking skills.
Beyond his on-court numbers, Lillard’s strong ties to the Portland community and his philanthropic efforts have solidified his beloved status among fans. His decision to return may soften any lingering hard feelings following his trade request, reinforcing his reputation as a player who values loyalty and roots over simply chasing championships.
The Broader Impact of Lillard’s Milwaukee Experience
Lillard’s challenging tenure in Wisconsin underscores the unpredictable nature of high-profile player acquisitions. The injuries sustained by both Lillard and Giannis prevented the duo from fulfilling the championship expectations envisioned by the Bucks organization and its fans. Meanwhile, Lillard’s living arrangements, including renting Holiday’s mansion and dealing with peculiar issues like Wi-Fi, add a relatable dimension to his professional journey.
The Bucks’ decision to move on from Lillard and focus on building around Giannis will likely shape their future roster strategy. For Lillard, returning to Portland offers a chance to write a new chapter that blends his scoring ability with leadership roles alongside the next generation of Blazers stars.
Our Reader’s Queries
Q. What surgery did Damian Lillard have?
A. Damian Lillard had a surgery today that went well to fix a torn Achilles tendon in his left leg. Dr. Neal ElAttrache did the operation in Los Angeles. Bucks orthopedic surgeon Dr. Carole Vetter also gave advice for the procedure.
Q. What does Damian Lillard have tattooed on his arm?
A. He’s been selected as an All-Star and has received several honors, such as the Rookie of the Year award in 2013. Overall, Damian Lillard chose the number 0 for his jersey to honor his roots in Oakland, and the cities of Ogden and Portland, where he has lived during key times in his life.