The Behind the Bucks Podcast has released a series of three episodes entitled The Damian Lillard Story. Episode 2 especially covers the later portions of his time in Portland and the key events that led to his being traded to the Milwaukee Bucks on September 17, 2023. The series is narrated by Chris Haynes, and all episodes can be listened to from the Bucks+ page on nba.com or pretty much anywhere podcasts can be found. Episode 2 is embedded at the bottom of the page.
This first painful event for Blazers’ fans mentioned in the podcast was the when Lamarcus Aldridge left in free agency for the San Antonio Spurs in July of 2015.