It turns out Act Two of Lillard's Hall of Fame career could end much like Act One in Portland, however: without a ring and with an earlier than expected exit. Just before he was moved, Lillard had signed an extension to keep him under contract through 2026, with a massive near-$60 million player option in 2026-27.

Apr 22, 2025; Indianapolis, Indiana, USA; Milwaukee Bucks guard Damian Lillard (0) dribbles the ball while Indiana Pacers forward Aaron Nesmith (23) defends during game two of first round for the 2024 NBA Playoffs at Gainbridge Fieldhouse. Mandatory Credit: Trevor Ruszkowski-Imagn Images / Trevor Ruszkowski-Imagn Images