Damian Lillard ‘Was Not Happy In Milwaukee,’ Never Wanted To Get Traded To Bucks

Damian Lillard “was not happy in Milwaukee” and never wanted to get traded to the Bucks, according to Aaron Fentress of The Oregonian.

When Lillard requested a trade from the Portland Trail Blazers in 2023, he wanted to land with the Miami Heat. However, Portland and Miami couldn’t agree to a deal. 

The Bucks acquired Lillard from the Trail Blazers in 2023. Lillard spent two seasons in Milwaukee and was never himself off the court since he was away from his family. 

“Also, he was not happy in Milwaukee,” Fentress said. “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.”

Lillard averaged 24.6 points, 4.5 rebounds and 7.0 assists with the Bucks. He tore his left Achilles tendon in the 2025 playoffs and will miss all of next season. 

Milwaukee waived and stretched Lillard, who was slated to make $113 million over the next two seasons with the Bucks. That amount will be stretched over the next five seasons.

Lillard signed a three-year, $42 million contract with the Trail Blazers. He gets to be around his kids while rehabbing his injury. 

A future Hall of Famer, Lillard will make $70 million next season from the Bucks and Trail Blazers. The veteran holds 17 Portland franchise records. 

Lillard played in 58 games for the Bucks last season. He averaged 24.9 points, 4.7 rebounds and 7.1 assists while shooting 44.8% from the field, 37.6% from beyond the arc and 92.1% from the free-throw line. 

A top 75 player of all time, Lillard has career averages of 25.1 points, 4.3 rebounds and 6.7 assists with the Trail Blazers and Bucks. He’s fourth in NBA history in 3-point field goals. 

Lillard has made nine All-Star teams and seven All-NBA teams. He won the 2012-13 Rookie of the Year Award with the Trail Blazers.