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.

Portland Trail Blazers guard Damian Lillard shared Jrue Holiday’s message after Bucks release, teasing backcourt that ended up materializing.