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.

Damian Lillard is now a Portland Trail Blazer for the second time, having re-signed with the team that drafted him in 2012 after he was waived by the Milwaukee Bucks on July 6. It was the end of a two-year sojourn with the Bucks, which unfortunately did not land him the championship he sought after asking to be traded out of Portland in 2023.