Damian Lillard’s brief run in Milwaukee is ending with revelations that the All-Star guard was unhappy throughout his tenure with the Bucks.
“He didn’t want to be there. He had to actively try to make sure he wasn’t miserable,” ESPN’s Tim MacMahon said, describing Lillard’s emotional state after being traded to the Eastern Conference contender.
Milwaukee waived the 34-year-old after two seasons, creating $113 million in cap space used to acquire Indiana center Myles Turner. The move ends a disappointing chapter that included an early playoff exit and Lillard’s torn Achilles in April.
Lillard posted 24.9 points and 7.1 assists per game in the 2024-25 season before the injury, remaining productive on the court despite growing discomfort behind the scenes.
According to Jake Fischer of Bleacher Report, Lillard remains connected to Portland, where he maintains an offseason home and is involved in community programs.
The Trail Blazers missed the postseason with a 36-46 record but have young talent and cap flexibility. Lillard’s return would immediately shift their outlook and potentially energize the fanbase.
The Bucks, who finished fifth in the East at 48-34, were eliminated in five games by the Pacers in the first round. With Lillard off the books, they gain flexibility to retool around Giannis Antetokounmpo and their new frontcourt addition.
Lillard now becomes one of the top available free agents, though his recovery timeline remains uncertain. He underwent surgery in May and is expected to miss the start of the 2025-26 season.
Still, several franchises are monitoring his status closely. The Los Angeles Lakers have been linked to Lillard, seeking additional backcourt help after being eliminated in the first round by Minnesota.
While no formal decision has been made, a reunion with the Trail Blazers appears increasingly plausible given the mutual history and Lillard’s deep community ties.
Lillard, a seven-time All-NBA selection, spent 11 seasons with Portland before being traded to Milwaukee in 2023.
