The basketball world was left stunned when Damian Lillard found himself back in a Portland Trail Blazers uniform. His return to the franchise where his NBA journey began in 2012 came after the Milwaukee Bucks made the shocking decision to waive him, despite his status as one of the greatest shooters of this generation.
Most believed his legacy would protect him, even while recovering from an Achilles injury.

What Made the Bucks’ Decision So Historic?
This move represents the biggest waiver-and-stretch in NBA history. The Bucks committed to paying Lillard $22.5 million annually for the next five years, ensuring the sharpshooter secures a substantial paycheck even if he steps away from the game entirely.
Back in Portland, where Lillard first established himself as a great player, he recently opened up about his time in Milwaukee and his experience playing alongside Giannis Antetokounmpo.
How Did Damian Lillard Describe Playing Alongside Giannis Antetokounmpo?
In a recent interview with the Milwaukee Journal Sentinel, Lillard spoke candidly about partnering with one of the modern era’s greatest forwards. “I thought it was a great experience, man. It was a great experience. I think more than anything just the luxury of playing with a player as great as him,” he said.
“I do everything I can to position myself and the team to do well, and he’s a guy that does all of those things with the same edge and worry. That was something I really appreciated, too,” Lillard added.
Lillard’s journey to Milwaukee began in 2023 following a lengthy saga of trade rumors that initially linked him to the Miami Heat. The Bucks instantly improved on paper with his addition, though the move caught many by surprise. With Lillard and Antetokounmpo sharing the court, Milwaukee appeared destined for greatness.
The duo did capture the NBA Cup in 2024, defeating the Oklahoma City Thunder in the final in Las Vegas. Interestingly, OKC went on to win the NBA Championship that same season, while the Bucks crashed out of the playoffs in the first round.
Why Couldn’t the Bucks Capitalize on Their Star Power?
Injuries proved to be the primary obstacle preventing Milwaukee from reaching their potential. They fell to the Indiana Pacers in the 2024 playoffs when Antetokounmpo was sidelined with a calf injury. Similarly, Lillard battled his own health issues this year, first dealing with deep vein thrombosis.
The nine-time All-Star managed to return for Game 4 this year, but ruptured his Achilles tendon, leaving him in agony. The Bucks’ superstars seemed plagued by unfortunate timing and bad luck.
In a surprising turn of events, Milwaukee offloaded Lillard’s contract to sign Myles Turner. Ultimately, the situation has worked out for everyone involved. Lillard is back home where his career began, while the Bucks look to bounce back in next year’s postseason.
