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 opens up about his relationship with Giannis Antetokounmpo after leaving the Bucks to join the Blazers.