The Bucks won their division in Lillard's first year and locked up the Eastern Conference's No. 3 seed prior to a first-round upset. They finished fifth in the conference last season and fell to the eventual NBA runner-up Indiana Pacers in the opening round. And with that, Lillard's chances of earning a ring before his eventual retirement dwindled.

The Milwaukee Bucks waived Damian Lillard this offseason after he spent two years with the team from 2023 to 2025. When the Bucks first acquired Lillard, there were high expectations that he and Giannis Antetokounmpo would potentially bring the Bucks another title together.