Damian Lillard ‘Was Not Happy in Milwaukee’ With Bucks

Portland Trail Blazers guard Damian Lillard was reportedly unhappy 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 said during Thursday’s episode of the Blazer Focused podcast at the 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. But the fit never really worked out.”

Damian Lillard Wanted To Win An NBA Title With Milwaukee?

Despite Fentress’ comments, fans are unsure what to believe because of conflicting reports.

On the latest episode of the Hoop Collective Podcast, ESPN’s Brian Windhorst said at the 13:20 mark that Lillard’s “preference” would have been to remain with the Bucks to have an opportunity to contend for a championship.

Arguably the biggest factor in Lillard’s decision to sign with the Trail Blazers was wanting to be closer to his kids, per Julie Evensen of The Oregonian.

On July 7, the Bucks officially waived Lillard and stretched the remaining $103 million left on his contract to help create roster space for free agent center Myles Turner, who signed a four-year, $107 million deal.

Lillard, 35, 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, $42 million contract on Thursday.

Bucks To Save $2.3 Million Annually With Lillard’s New Deal

According to ESPN’s Bobby Marks, the Bucks will receive a salary cap benefit as a result of Lillard’s new contract with Portland. When Milwaukee stretched and waived the former first-rounder, that resulted in annual cap hits of about $22.5 million.

Per Marks, since Lillard’s salary with Portland exceeds the one-year veteran’s minimum salary ($2,048,494) for each of the next two seasons, the Bucks will receive a set-off amount of approximately $11.65 million.

The formula for calculating the exact amount involves taking Lillard’s new salary with the Blazers, subtracting the one-year vet minimum, and dividing that amount in half.

The set-off, which will be applied after the 2025-26 regular season, will reduce Milwaukee’s annual dead-money cap hits from $22.5 million to $20.2 million through 2029-30.

Lillard Earned Two All-Star Nods With Milwaukee

Lillard experienced some individual success with the Bucks, earning All-Star selections in each of his two seasons with the team while averaging 24.6 points, 4.5 rebounds, and 7.0 assists per game with Milwaukee.

The 13-year veteran recorded a season-high 43 points against the Philadelphia 76ers on Feb. 9 before being sidelined for Milwaukee’s final 14 games of the regular season.

The Bucks went 10-4 in those contests and ended the regular season on an eight-game winning streak.

Milwaukee, however, suffered first-round playoff exits against the Indiana Pacers in each of the past two seasons. Lillard also missed time in both series due to injuries, including a torn Achilles in Game 4 of the Bucks’ 2025 series with the Pacers.