According to Aaron J. Fentress, a pioneer reporter from the Oregonian, Lillard was unhappy in Milwaukee and never thought he would be traded to the Bucks.
According to previous reports, Lillard wanted to be traded to the Heat when applying for a deal in 2023, but the Trail Blazers and the Heat failed to reach an agreement. The Bucks got Lillard through a trade in 2023, who spent two seasons in Milwaukee. Lillard almost never left the court when he was away from his family.
Fentress said: "Lillard was not happy in Milwaukee. He didn't want to go to Milwaukee at first, he wanted to go to Miami. But the agent convinced Lillard, who made a concession and went to Milwaukee."