In the 2023 offseason, the Portland Trail Blazers made a shocking move to ship Damian Lillard to the Milwaukee Bucks in a three-team trade. Before this move, Lillard spent the first 11 years of his NBA career in Portland, but the opportunity to team up with two-time MVP Giannis Antetokounmpo in Milwaukee had to be too hard to pass up on.
However, after just two years with the Bucks and a torn Achilles in the 2025 playoffs, Milwaukee and Lillard parted ways. The nine-time All-Star hit the open market after being waived, and who did he decide to sign with? None other than the Trail Blazers.
Despite being out for the entire 2025-26 season, Lillard went to All-Star weekend to represent Portland in the Three-Point Contest. While at All-Star weekend, Lillard spoke about why he decided to sign with the Trail Blazers in the offseason.
“When I had an opportunity to go to any team, I picked this team. I picked the team because, for one, it’s the team that I wanted to win a championship with all along. And two, the team is in position, in my eyes, to do that. Especially with me being a part of it. I think we do have a chance. It was an easy decision,” Lillard said about re-signing with Portland.