Blazers’ Damian Lillard reveals immediate Jrue Holiday message after Bucks release

“As soon as I got waived, he sent me the

emoji”

The significance wasn’t lost on the 13-year veteran. He interpreted the emoji as a signal from Holiday that the door was open for a return to Portland. For the 35-year-old point guard, it marked a full-circle moment after being traded to the Bucks in 2023 as part of a deal that originally involved Holiday. While Lillard spent two seasons in Milwaukee, averaging 25.7 points per game, Holiday found success with the Boston Celtics, helping the team win the 2024 NBA title. But the guard was traded back to Portland this June for Anfernee Simons, just one month before the Bucks waiver cleared Lillard’s cap-heavy contract from their books.

Now, both players find themselves on the same rebuilding team that finished 36-46 last season. For Holiday, who is 35-years-old, the pairing offers not only veteran leadership but emotional continuity. His experience winning at the highest level adds a proven pedigree to a Trail Blazers team in transition. That background could help propel Portland to the next step in its rebuild.

Holiday’s message, and the lighthearted story Lillard shared—about discussing Wi-Fi in the house he rented from Holiday in Milwaukee after they were traded for each other—only reinforced how close their connection has remained despite never being teammates until now.

Their careers have long been intertwined, dating back to the Blazers icon attempted to recruit Holiday to Portland in 2021. That never materialized—until now. What began as an emoji may evolve into one of the more compelling veteran backcourts in the Western Conference, especially if both players remain healthy through the upcoming season.

Though the NBA free agency market remains active, few moves carry the emotional weight or fan intrigue of this new pairing. With Portland leaning on young talent and smart contracts, Lillard and Holiday could serve as crucial guides on and off the court.

If nothing else, the “

” text may go down as one of the most memorable recruiting pitches of the summer.