When Lillard was originally traded to Milwaukee, his preferred landing spot was the Miami Heat, but with Jimmy Butler no longer on the team, and the Heat further away from title contention than they were when Lillard was originally on the trading block, that pairing seems unlikely.

Damian Lillard tore his Achilles during Game 4 of the Milwaukee Bucks' first-round playoff loss to the Indiana Pacers. Lillard underwent successful surgery a few days later, but the injury still meant the end of his time with the Bucks as the team chose to stretch his contract and waive him to make him a free agent.

The Bucks acquired Lillard from the Trail Blazers in a three-team blockbuster deal with the Suns in 2023, shipping out Jrue Holiday, Grayson Allen, a 2029 first-rounder and first-round pick swaps in 2028 and 2030.