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.

Portland Trail Blazers general manager Joe Cronin gets honest about watching Damian Lillard play for the Milwaukee Bucks.

There is a valid argument that claims the Milwaukee Bucks experiment pairing Giannis Antetokounmpo and Damian Lillard together was a failed one. Two consecutive first-round playoff exits are the most damaging element of the duo’s short-lived time together.