Damian Lillard’s first training session in Milwaukee after spending 11 years with the Portland Trail Blazers left an unforgettable mark on him.
In an era when players do not think twice before demanding a trade in hopes of winning an NBA Championship, Damian Lillard waited 11 years before giving up on the Portland Trail Blazers.
During his time with the Trail Blazers, Lillard established himself as one of the top stars in the league but could never take the organization to a championship run in the postseason.
After more than a decade of suffering through mediocrity, Lillard finally demanded a trade and was sent to the Milwaukee Bucks as part of a blockbuster deal.
Changing teams after more than a decade is never easy, and Lillard experienced that during his first practice with his new team.
“Discomfort. Once I felt a little uncomfortable like, damn, I don’t know where I’m at. I’m driving, play zone or where I’m at,” Lillard told NBA insider Chris Haynes.
“This isn’t my team. I’m joining Giannis’ team. I’m joining a new organization.”
Even though Dame has been with the Bucks for nearly two years, the organization will always remain Giannis Antetokounmpo’s team.
After all, he is a home-grown talent who led the Bucks to a famous NBA Championship run in 2021.
Wearing a new organization’s jersey, Lillard was pushed out of his comfort zone. But it ultimately helped him find a new fight and beat it.
“I wasn’t in my comfort zone. It was a new fight for me that I hadn’t had to fight for over a decade. So it just kind of presented me like some hurdles. You know, it gave me something to go against.”
Fast forward to 2025, Lillard has grown as a player and leader for the Bucks as he has helped the team reach the fourth seed in the Eastern Conference, albeit after a poor start to the season.
