Damian Lillard spent the first 11 seasons of his career with the Portland Trail Blazers, becoming a franchise legend and one of the NBA’s top 75 players over that time.But despite his 3-point prowess and penchant for hitting incredible shots in the game’s biggest moments, he never found true team success, reaching the conference finals only once.In the summer of 2023, Lillard requested a trade to a championship contender.
What followed was a three-year roller-coaster ride beginning with protracted trade negotiations, a surprising move to the Milwaukee Bucks, an imperfect partnership with superstar teammate Giannis Antetokounmpo and more playoff heartbreak.Then, in 2025, in the midst of a second straight first-round postseason exit, Lillard tore an Achilles.
A few months later, Milwaukee made the shocking decision to waive Lillard with two years and $113 million left on his contract.The ups, downs, loops, twists and turns ultimately led Lillard back to Portland, which signed him back in July 2025.
Lillard says the Blazers were the first team to knock on his door after the Bucks let him go.“I’m really thankful that as soon as I was waived, it was the first opportunity presented to me,” Lillard told NBC News on the eve of the season of how he ended up back in Portland.“They know that I can be counted on.
They knew that I wasn’t gonna accept the injury and just be done.They knew how I was gonna respond to that.”The path back to the Blazers certainly wasn’t easy.
Lillard landed in Milwaukee on a team loaded with championship expectations.During his first season with the Bucks, the franchise changed head coaches.
Meanwhile, his chemistry with Antetokounmpo — who has since been traded himself — was constantly called into question.Even as Lillard continued to average more than 24 points per game, the team couldn’t find consistent success.
Injuries marred both postseason runs as Lillard and Antetokounmpo appeared in only four playoff games toge...