Damian Lillard “wasn’t happy” in Milwaukee before Bucks waived him
Portland Trail Blazers guard Damian Lillard reportedly wasn’t thrilled about his time with the Milwaukee Bucks before the team waived him, according to Aaron Fentress of The Oregonian.
“He was not happy in Milwaukee,” Fentress revealed during Thursday’s episode of the Blazer Focused podcast. “He didn’t want to go there in the first place, he wanted to go to Miami.”
Lillard apparently only agreed to the Milwaukee move because his agent convinced him it gave him a better shot at winning a championship.
“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.”
Mixed signals about Lillard’s Bucks experience
Fans are scratching their heads about what to believe, as different reports tell different stories.
ESPN’s Brian Windhorst said on the Hoop Collective Podcast that Lillard would have actually preferred to stay with the Bucks to keep chasing a championship.
But family matters seem to have played a huge role in his decision-making. According to Julie Evensen of The Oregonian, wanting to be closer to his kids was probably the biggest factor in Lillard signing with the Trail Blazers.
The Bucks officially cut ties with Lillard on July 7, stretching the remaining $103 million on his contract to make room for free agent center Myles Turner, who signed a four-year, $107 million deal.
After exploring his options, the 35-year-old Lillard returned to Portland, where he spent the first 11 years of his career. He signed a three-year, $42 million contract on Thursday.
Bucks will save some cash with Lillard’s new deal
There’s a small silver lining for Milwaukee in all this.
According to ESPN’s Bobby Marks, the Bucks will actually get some salary cap relief thanks to Lillard’s new Portland contract. When they stretched and waived him, Milwaukee was looking at annual cap hits of about $22.5 million.
But since Lillard’s new salary with Portland is higher than the veteran’s minimum ($2,048,494) for the next two seasons, the Bucks will receive about $11.65 million in set-off money.
The math is a bit complicated. They take Lillard’s new Blazers salary, subtract the one-year vet minimum, and divide that in half.
This set-off will kick in after the 2025-26 season and will lower Milwaukee’s annual dead-money cap hits from $22.5 million to $20.2 million through 2029-30.
Dame still shined in Milwaukee despite team struggles
Lillard did have some personal success with the Bucks, making the All-Star team in both his seasons there. He averaged 24.6 points, 4.5 rebounds, and 7.0 assists per game during his time in Milwaukee.
He put up a season-high 43 points against the Philadelphia 76ers on Feb. 9 before missing Milwaukee’s final 14 regular-season games.
The Bucks actually went 10-4 without him and finished the regular season on an eight-game winning streak.
But when it really mattered, things fell apart. Milwaukee got bounced in the first round of the playoffs by the Indiana Pacers in both seasons. Lillard missed time in both series due to injuries, including a torn Achilles in Game 4 of the Bucks’ 2025 series with the Pacers.
