In a timeline where the Jae Crowder trade went down, there's no way one can say the move to add Damian Lillard was worse for the Milwaukee Bucks. Nevertheless, ESPN's Zach Kram highlighted the Lillard deal, calling it Milwaukee's worst roster move of the 2020s in a recent article. One could make an argument, sure, but the Crowder trade still stings.
Knowing what the Bucks knew at the time, opposing teams would have done the Damian Lillard deal if they had the chance. Who wouldn't want to pair two top 75 players together to forge one of the best one-two punches in the NBA?