Blazers' Damian Lillard Reportedly 'Was Not Happy in Milwaukee' Before Bucks Exit

Portland Trail Blazers guard Damian Lillard wasn't enjoying his time as a member of the Milwaukee Bucks before the team waived him, according to Aaron Fentress of The Oregonian.

"Also, he was not happy in Milwaukee," Fentress reported on Thursday's episode of the Blazer Focused podcast (2:55 mark). "He didn't want to go there in the first place, he wanted to go to Miami. He relented and went to Milwaukee because his agent talked him into it, right? It gave him a chance to win."

"He wasn't necessarily happy, there wasn't anything against Milwaukee or the Bucks or anything like that where he didn't necessarily want to be there, he did want to win," he added. "But the fit never really worked out."

On July 7, the Bucks officially waived Lillard and stretched the remaining $103 million left on his contract to help facilitate the signing of free-agent center Myles Turner on a four-year, $107 million deal.

Lillard explored his options in free agency before eventually returning to a Trail Blazers organization that he spent the first 11 years of his career with, signing a three-year contract worth $42 million on Thursday.

The 35-year-old experienced individual success during his tenure in Milwaukee, earning All-Star nods in each of his two years with the team while averaging 24.6 points and 7.0 assists per game with the Bucks.

Milwaukee suffered first-round playoff exits at the hands of the Indiana Pacers in each of the past two seasons, though. Lillard missed time in both series defeats due to injuries, suffering a torn Achilles in Game 4 of the Bucks' 2025 clash with the Pacers.

As the star point guard looks to recover in Portland, he reportedly wasn't happy when he was a member of his former team.