Damian Lillard Shares Hilarious Anecdote Involving Jrue Holiday

Damian Lillard is set to make his return to the Portland Trail Blazers on a three-year deal, teaming up with guard Jrue Holiday, who was recently acquired from the Boston Celtics. The duo's names have been intertwined since Lillard's trade to the Milwaukee Bucks, which involved Holiday, who was later moved to the Celtics shortly after. While this is their first time as teammates, their bond has been strengthened since Lillard rented Holiday's home in Milwaukee during his time with the Bucks. Reflecting on his stay, Lillard humorously noted that the biggest challenge was the poor WiFi connection. Their frequent discussions largely revolved around his frustrations with it. Lillard shared, “During my two years in Milwaukee, I often complained to him about the WiFi.” He recounted a particular moment in Boston when their handshake sparked curiosity, as they were actually discussing his internet troubles. As Lillard rehabilitates from a torn Achilles, he may embrace a mentoring role, eagerly anticipating playing alongside Holiday in the 2026–27 season.