Fans thought the days of Damian Lillard wearing a Portland Trail Blazers jersey were in the past. They hoped he'd sign a one-day contract with the Trail Blazers so that he could officially retire with the organization. Nobody guessed that he'd return two years after he requested a trade, not to retire, but to rehab and prepare for another couple of seasons of play.
Lillard signed a three-year, $42 million contract with Portland this summer, weeks after he suffered an Achilles tear in the playoffs. The Trail Blazers didn't let Lillard's previous trade request get in the way of a reunion. They welcomed him back with open arms.
After Portland finished the 2022-23 season with a 33-49 record, Lillard made it known that he wanted the team to prioritize adding proven veterans to the roster rather than embracing youth. The Trail Blazers left the draft lottery with the No. 3 pick, which they used to select Scoot Henderson in June, rather than trading it.
Joe Cronin said Portland was still "committed to building a winner" around Lillard, but a few days later, the star guard officially requested a trade to Miami. The trade saga lasted for nearly three months before the Trail Blazers sent Lillard to the Bucks in a three-team deal. Just like that, the Dame Era was over.
Damian Lillard couldn't stay away from the Trail Blazers for too long
Lillard wanted to compete for a championship, but that didn't happen in Milwaukee alongside superstar Giannis Antetokounmpo. The Bucks were first-round exits in Lillard's two seasons with the team, winning a total of three postseason games. Lillard tore his Achilles in Game 4 of the 2025 playoffs, and Milwaukee's season officially ended at the conclusion of Game 5.
The Bucks decided to waive and stretch the remaining $103 million left on his contract, paving the way for him to be a free agent. There was talk of him joining a team like the Celtics, rehabbing alongside Jayson Tatum and competing for a championship during the 2026-27 season, but he wanted to return to his NBA home.
Portland wanted him back, too.
Cronin said, "It never felt right seeing Damian in a different jersey. We're really excited to bring him back to Portland.
Lillard will spend next season rehabbing, preparing to do what he's always wanted to do — win a title with the Trail Blazers. It's a daunting challenge, made tougher by coming back from that kind of injury at 35 years old (he'll turn 36 before the start of the 2026-27 season), but Dame understands that. He could've taken an "easier" route by signing with a contender, but there is only one place he wanted to be.
It's Dame Time again.